BIOMOLECULES , POLYMERS & POC

1. IIT-JEE Syllabus

Carbohydrates: Classification – mono, di and polysaccharides (Glucose, Sucrose and

Starch only); hydrolysis of sucrose. Amino acids and Peptides: General structure and
physical properties. Properties and uses of some important polymers (natural rubber,
cellulose, nylon, teflon, PVC),

2. Carbohydrates

2.1 Introduction

The group of compounds known as carbohydrates received their general name because of early
observations that they often have the formula Cx(H2O)y - that is, they appear to be hydrates of
carbon.

Limitations: The above definition could not survive long due to the following reasons:

i) A number of compounds such as rhamnose, (C6H12O5) and deoxyribose (C5H10O4) are known
which are carbohydrates by their chemical behaviour but cannot be represented as hydrates
of carbon.

ii) There are other substances like formaldehyde (HCHO, CH2O) and acetic acid [CH3COOH, C2
(H2O)2] which do not behave like carbohydrates but can be represented by the general
formula, Cx(H2O)y.

Carbohydrates are defined as polyhydroxy aldehydes or polyhydroxy ketones or substances

which give these on hydrolysis and contain at least one chiral carbon atom. It may be noted here
that aldehydic and ketonic groups in carbohydrates are not present as such but usually exist in
combination with one of the hydroxyl group of the molecule in the form of hemiacetals and
hemiketals respectively.

2.2 Classification

Chemically carbohydrates are polyhydroxy aldehydes or ketones or substances that yield these on
hydrolysis.
(A) ON THE BASIS OF FUNCTIONAL GROUPS:
Carbohydrates with an aldehydic group are known as aldoses and those with
ketonic group are called ketoses. The number of carbon atoms in a carbohydrate (monomer
unit) is indicated by prefix tri, tetra, penta etc. The name of the carbohydrate containing aldehydic
group end in “ ose” while suffix for ketonic group is “ ulose”.
For example,
4carbon containing aldehydic carbohydrate is tetrose. [OHCH2(CHOH)2CHO].
It contains two chiral carbon and the name of optical isomers are Derythrose, Dthreose,
Lerythrose, Lthreose.
4carbon containing ketonic carbohydrate is called keto tetrose [OHCH2.CO.CHOH.CH2OH].
It contains 1chiral carbon and name of optical isomers are D & Lerythrulose.

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(B)On the basis of number of monosaccharide units (saccharide is latin name for sugar)
carbohydrate yields on hydrolysis.
Carbohydrates are divided into two main classes, sugar and polysaccharides. Sugars are
crystalline substance with a sweet taste and soluble in water. Polysaccharides are more complex
than sugar, their molecular weight being far greater, are noncrystalline substances which are
not sweet and are insoluble or less soluble in water.
Examples of sugar

i) Monosaccharides: The monosaccharides are polyhydroxy aldehydes or polyhydroxy ketones

which cannot be decomposed by hydrolysis to give simpler carbohydrates. Examples are
glucose and fructose, both of which have molecular formula, C6H12O6.

H
C 6H 12O6 + H2O 
 No reaction
glucose or
fructose

ii) Oligosaccharides: The oligosaccharides (Greek, oligo, few) are carbohydrates which yield a
definite number (2-9) of monosaccharide molecules on hydrolysis. They include,

a) Disaccharides, which yield two monosaccharide molecules on hydrolysis. Examples are

sucrose and maltose, both of which have molecular formula, C12H22O11.

H
C12H22O11 + H2O 
 C6H12O6 + C6H12O6
sucrose glucose fructose


H
C12H22O11 + H2O 
 2C6H12O6
Maltose glucose
Trisaccharides, which yield three
monosaccharide molecules on hydrolysis. Example is, raffinose, which has molecular
formula, C18H32O16.

H
C18H32O16 + 2H2O 
 C6H12O6 + C6H12O6 + C6H22O6
raffinose glucose fructose galactose

iii) Polysaccharides: The polysaccahrides are carbohydrates of high molecular weight which
yield many monosaccharide molecules on hydrolysis. Examples are starch and cellulose,
both of which have molecular formula, (C6H10O5)n.

H
(C6H10O5)n + nH2O 
 nC6H12O6
starch glucose

In general, the monosaccharides and oligosaccharides are crystalline solids, soluble in water
and sweet to taste. They are collectively known as sugars. The polysaccharides, on the other
hand, are amorphous, insoluble in water and tasteless. They are called non-sugars. The
carbohydrates may also be classified as either reducing or non-reducing sugars. All those
carbohydrates which have the ability to reduce Fehling’s solution and Tollen’s reagent are
referred to as reducing sugars, while others are non-reducing sugars. All monosaccharides
and the disaccharides other than sucrose are reducing sugars.

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3. Monosaccharides

The monosaccharides are the basis of carbohydrate chemistry since all carbohydrates are either
monosaccharides or are converted into monosaccharides on hydrolysis. The monosaccharides
are polyhydroxy aldehydes or polyhydroxy ketones. There are, therefore, two main classes of
monosaccharides.
O
||
1. the Aldoses, which contain an aldehyde group (  C  H)
O
||
2. the Ketoses, which contain a ketone group (— C —)

The aldoses and ketoses are further divided into sub-groups on the basis of the number of
carbon atoms in their molecules, as trioses, tetroses, pentoses, hexoses, etc. To classify a
monosaccharide completely, it is necessary to specify both, the type of the carbonyl group and
the number of carbon atoms present in the molecule. Thus monosaccharides are generally
referred to as aldotrioses, aldotetroses, aldopentoses, aldohexoses, ketohexoses, etc. Glucose
and fructose are specific examples of an aldose and a ketose.
H O CH2OH
|
C C=O
| |
H – C – OH HO – C – H
| |
HO – C – H H – C – OH
| |
H – C – OH H – C – OH
| |
H – C – OH CH2OH
|
CH2OH fructose
Glucose (an aldohexose) (a ketohexose)

3.1 Trioses

D and L Terminology: The simplest of all CHO CH2OH

carbohydrates that fit the definition we have | |
given for carbohydrates are the trioses, *CHOH C=O
glyceraldehyde and dihydroxyacetone. | |
Glyceraldehyde is aldotriose, and CH2OH CH2OH
Glyceraldehyde Dihydroxyacetone
dihydroxyacetone is a ketotriose. (an aldotriose) (a ketotriose)

Glyceraldehyde contains one asymmetric CHO CHO

| |
carbon atom (marked by an asterisk) and can H – C – OH HO – C – H
thus exist in two optically active forms, called | |
the D-form and the L-form. Clearly, the two CH 2OH CH2OH
D-Glyceraldehyde L-Glycera aldehyde
forms are mirror images that cannot be
superimposed, that is they are enantiomers.

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O O
|| ||
1 1
CH D Means on CH
| the right |
2 2
H – C – OH HO – C – H
| | L Means on
3 3 the Left
CH2OH CH2OH
D-Glyceraldehyde L-Glyceraldehyde

The two forms of glyceraldehyde are especially important because the more complex
monosaccharides may be considered to be derived from them. They serve as a reference point
for designating and drawing all other monosaccharides. In carbohydrate chemistry, the Fischer
projection formulas are always written with the aldehyde or ketone groups at the top of the
structure. By definition, if the hydroxyl group on the asymmetric carbon atom farthest from
aldehyde or ketone group projects to the right, the compound is a member of the D-family. If the
hydroxyl group on the farthest asymmetric carbon projects to the left, the compound is a member
of the L-family. The maximum number of optical isomers of a sugar is related to the number of
asymmetric carbon atoms in the molecule and may be calculated by the following simple
equation.
Maximum Number of Optical Isomers = 2n, where n = the number of asymmetric carbon
atoms.
Since glyceraldehyde contains only one asymmetric carbon atom, the number of optical isomer
is 21. We know that 21 is = 2, and we have seen that there are indeed two different
glyceraldehydes.

3.2 Aldotetroses

If we examine the general formula of an aldotetrose, 1. CHO

we see that they contain two asymmetric carbon |
atoms (marked by asterisks). 2. *CHOH
|
3. *CHOH
This means that 22 or 4 optical isomers are |
possible. They may be represented as the following 4. CH2OH
an aldotetrose
two pairs:
CHO CHO CHO CHO
| | | |
H – C – OH HO – C – H HO – C – H H – C – OH
| | | |
H – C – OH HO – C – H H – C – OH HO – C – H
| | | |
CH2OH CH2OH CH2OH CH2OH
Mirror images (recemic pair) Mirror images (recemic pair)
D (–)-erythrose L (+)-erythrose D (–)-threose L (+)-threose

All four isomers have been prepared synthetically. The D- and L-erythrose are mirror images,
that is, they are enantiomers. They have exactly the same degree of rotation but in opposite
directions. Equal amounts of the two would constitute a racemic mixture, that is, a mixture that
would allow a plane-polarised light to pass through the solution unchanged but could be
separated into detrorotatory and laevorotatory isomers. The same comments hold for D- and L-
threose. However, D-erythrose and L-threose are not images, that is, they are diastereomers
(optical isomers that are not mirror images are called diastereomers), and the degree of rotation
of each would probably differ.

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3.3 Aldohexoses

If we examine the general formula of aldohexose, we see that it 1. CHO

contains four asymmetric carbon atoms. |
2. *CHOH
This means that 24 or 16 optical isomers are possible. D and L |
forms of altrose, allose glucose, mannose, galactose, talose, 3. *CHOH
arabinose and idose |
4. *CHOH
Only three of the sixteen possible aldohexoses are found in |
nature (all sixteen isomers have been prepared synthetically). 5. *CHOH
They are D-glucose, D- mannose, and D-galactose. No one of |
these three optical iosmers is a mirror image of any of the others, 6. CH2OH
so all three are diastereomers of each other. an aldohexose

3.4 Epimers

A pair of diastereomers that differ only in Epimers Epimers

O H O H O
the configuration about of a single carbon H
atom are said to be epimers. e.g D(+)- C C C
glucose is epimeric with D(+) -mannose | | |
H – C – OH H – C – OH HO– C – H
and D(+) -galactose as shown below:
| | |
HO– C – H HO– C – H HO– C – H
| | |
HO– C – H H – C – OH H – C – OH
| | |
H – C – OH H – C – OH H – C – OH
| | |
CH2OH CH2OH CH2OH
D (+)-Galactose D (+)-Glucose D (+)-Mannose

3.65 Cyclic structure of monosaccharides

We know that aldoses (and ketoses) react with alcohols to give first hemiacetals (and
hemiketals) and then acetals (and ketals), i.e.,

OH OR
| |
ROH
– C = O + ROH – C – OR  
 – C – OR
–H2O
| | |
H H H
Aldehyde Hemiacetal Acetal

OH OR
| | |
ROH
– C = O + ROH – C – OR  
  – C – OR
–H2O
Ketone Hemiketal ketal

Since monosaccharides contain a number of hydroxyl groups and an aldehyde or a keto group,
therefore, any one of the –OH groups (usually C4 or C5 in aldohexoses and C5 or C6

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in ketohexoses) may combine with the aldehyde or the
keto group to form intramolecular hemiacetal or
hemiketal. As a result, the open chain formulae do not
represent the actual structures of the monosaccharides.
Their actual structures are cyclic involving five or six O O
membered rings containing an oxygen atom. The five Furan Pyran
membered ring containing one oxygen atom because of its similarity with furan is called the
furanose form and the six membered ring containing one oxygen atom because of its
resemblance with pyran is called the pyranose form. In nut shell, all the monosaccharides
(pentoses and hexoses) in the free state always exist in the pyranose form. However, in the
combined state some monosaccharides such as ribose, 2-deoxyribose, fructose etc., usually
exist in the furanose form.

3.6 Cyclic structure of Glucose – Anomers

1  1
1
H – C – OH H– C=O HO – C – H
| | |
2 2 2
H – C – OH H – C – OH H – C – OH
| | |
3 3 3
HO– C – H O HO– C – H HO– C – H O
| | |
4 4 4
H – C – OH H – C – OH H – C – OH
| | |
5 5 5
H– C H– C–O–H H– C
| | |
6 6 6
CH2OH CH2OH CH2OH (II)
(I)
-D(+)-Glucose or D(+)-Glucose -D(+)-Glucose or
-D(+)-Glucopyranose (Open chain form) -D(+)-Glucopyranose

We have discussed above that monosaccharides have cyclic hemiacetal or hemiketal structures.
To illustrate, let us first consider the example of D-glucose. During hemiacetal formation C5 – OH
of glucose combines with the C1 – aldehydic group. As a result, C1 becomes chiral or asymmetric
and thus has two possible arrangements of H and OH groups around it. In other words, D-
glucose exists in two stereoisomeric forms, i.e., -D-glucose and -D-glucose as shown below:

In -D-glucose, the OH group at C1 is towards right while in -D-glucose, the OH group at C1 is

towards left. Such a pair of stereoisomers which differ in configuration only around C1 are called
anomers and the C1 carbon is called Anomeric carbon (or glycosidic carbon. The cyclic
structures of monosaccharides can be better represented by Haworth Projection formulae. To
get such a formula for any monosaccharide (say -and -D-glucose), draw a hexagon with its
oxygen atom at the upper right hand corner. Place all the groups (on C1, C2, C3 and C4) which
are present on left hand side in structures I and II, above the plane of the ring and all those
groups on the right hand side below the plane of the ring.

The terminal – CH2OH group is always placed above the plane of the hexagon ring (in D-series).
Following the above procedure, Haworth Projection Formulae for -D-glucose (I) and -D-
glucose (II) are obtained as shown below:

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6 CH2OH 6 CH2OH

5 5
H H H OH

H H
4 1 4 1
OH H  OH H
OH OH OH H
3 2 3 2
I II
H -D-Glucose OH H -D-Glucose
or -D(+)-Glucopyranose
OH
or -D(+)-Glucopyranose

3.7 Cyclic structure of Fructose

Like glucose, fructose also has a cyclic structure. Since fructose contains a keto group, it forms
an intramolecular hemiketal. In the hemiketal formation, C5– OH of the fructose combines with
C2-keto group. As a result, C2 becomes chiral and thus has two possible arrangements of
CH2OH and OH group around it. Thus, D-fructose exists in two stereoisomeric forms, i.e., -D-
fructopyranose and -D fructopyranose. However in the combined state (such as sucrose),
fructose exists in furanose form as shown below:

6
2 1 CH2OH O
HO – C – CH2OH OH
| 
3
H – C – OH O 5 2
|
4
H – C – OH H H H CH2OH
| 1
5
H– C
4 3
|
6
CH2OH -D-Fructofuranose OH OH

3.8 Mutarotation

The two stereoisomeric forms of glucose, i.e., -D-glucose and -D-glucose exist in
separate crystalline forms and thus have different melting points and specific roations.
For example -D-glucose has a m.p. of 419 K with a specific rotation of +112° while -
D-glucose has a m.p. of 424 K and has a specific rotation of +19°. However, when either
of these two forms is dissolved in water and allowed to stand, it gets converted into an
equilibrium mixture of -and -forms through a small amount of the open chain form.

-D-Glucose Open chain form -D-Glucose

(36%) (0.02%) (64%)

As a result of this equilibrium, the specific rotation of a freshly prepared solution of -

D-glucose gradually decreases from of +112° to +52.7° and that of -D-glucose
gradually increases from +19° to +52.7°.

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This change in specific rotation of an optically active compound in solution with time,
to an equilibrium value, is called mutarotation. During mutarotation, the ring opens and
then recloses either in the inverted position or in the original position giving a mixture
of -and--forms. All reducing carbohydrates, i.e., monosaccharides and disacchardies
(maltose, lactose etc.) undergo mutarotation in aqueous solution.

3.9 Reactions of Glucose

1. MILD OXIDATION
Mild oxidation of aldoses gives aldonic acid. Br2 water or alkaline solution of iodine oxidises only
the aldehydic group to give aldonic acids.

2. STRONG OXIDATION
Strong oxidation of aldoses oxidise both CHO group and terminal CH2OH group into COOH
to give aldaric acid.

3. REDUCTION OF SUGAR
Sugar can be reduced into corresponding alcohols by variety of reducing agents like
high pressure catalytic hydrogenation (Ni/H2), NaBH4, (iii) Na/Hg (iv) electrolytic reduction in
acidic medium.

4. REACTION OF ALDOSE AND KETOSE WITH PHENYL HYDRAZINE

Aldose and ketose both react with phenyl hydrazine (excess) to form osazones, which contain
two phenylhydrazone group and also give aniline and ammonia. The overall reaction may be
represented as.
N
CHO HC=NNHPh HC NHPh
PhNHNH2
CHOH CHOH HOCH

N NH NH
HC NHPh NHPh HC + PhNH2
HC
CH C C=O
H
OH O

Ketoses (for example, Fructose) also react with phenyl hydrazine in similar way
O O
CHOH H H
CH C
PhNHNH2 PhNH2
C=O C=NNHPh C NHPh
NH

O NNHPh
+2PhNHNH2
HC HC + NH3 + H2O
PhNH2
C=NH C=NNHPh

Only C1 and C2 in glucose and fructose are involved in osazone formation and the reaction do
not run through out the chain. This is because osazone formed is stabilised by chelation.

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NHPh
6
HOH2C O N
5 1 H
4 2 N
3
OH N Ph
OH
Fig. 5.1

Glucose and fructose both form same osazone. This means configuration of glucose and
fructose is similar at all the carbons except C1 and C2.

5. REACTION WITH CONCENTRATED HCl

This reaction is only given by aldohexoses and aldopentoses. When aldohexoses are treated
with conc. HCl (or H2SO4), they first give hydroxymethyl furfural, which then decomposes into
other products.

conc . HCl
HOCH2(CHOH)4CHO    3H2O +
HOH2C O CHO

6. REACTION WITH ACID CHLORIDES AND ACID ANHYDRIDES

When monosaccharides are acylated with acetyl chloride in presence of anhydrous ZnCl2, all the
hydroxyl groups are acylated. For example, glucose gives a pentaacetate.
CHO Anhydrous CHO
ZnCl2
(CHOH)4 + 5CH3COCl (CHOOCCH3)4 + 5HCl
CH2OH Acetyl chloride CH2OOCCH3
Glucose Glucose pentaacetate

7. REACTION WITH PCl5

When treated with PCl5, all the hydroxyl groups are chlorinated.
CHO CHO
(CHOH)4 + 5PCl5 (CHCl)4 + 5POCl3 + 5HCl
CH2OH CH2Cl
Glucose Pentachloroglucose
(Glucose pentachloride)

8. REACTION WITH METALLIC HYDROXIDES

Glucose reacts as a weak acid and on reaction with calcium hydroxide to form calcium
gluocosate.
C6H11O5OH + HOCaOH C6H11O5OCaOH + H 2O
Calcium hydroxide  and Calcium glucosate

9. FORMATION OF GLYCOSIDES
Glucose reacts with methyl alcohol in presence of dry HCl to form  and methyl glycoside of
glucose. The reaction takes place only on OH of hemiacetylic carbon. Other hydroxyl groups
are unreactive.

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To methylate all the OH groups, methylating agent used is dimethyl sulphate.

H OCH3 CH3O H
C C

(CHOH)3 O (CHOH)3 O

CH CH

CH2OH CH2OH
Methyl glucose Methyl glucose

Fig. 5.2

10. REACTION OF CARBONYL GROUP (ALDEHYDIC GROUP)

Glucose is reduced by sodiumamalgam in presence of acid into corresponding hydroxyl
compound, sorbitol.
NaHg
CH2OH(CHOH)4CHO + 2H CH2OH(CHOH)4CH2OH
H2O
Glucose HO Sorbitol

11. REACTION WITH HCN

HCN reacts with glucose to form an addition product, glucose cyanohydrin.
CN
CH2OH(CHOH)4CHO + HCN CH2OH(CHOH)4CH
Glucose H O
Glucose cyanohydrin OH

12. REACTION WITH HIO4

Glucose consumes five moles of HIO4 to give five moles of formic acid and one mole of
formaldehyde. Fructose consumes five moles of HIO4 to give three moles of formic acid, two
moles of formaldehyde and one mole of CO2.

13. KILIANI FISCHER SYNTHESIS

The aldoses can be stepped up with the help of following sequence of reactions. Aldose is
treated with NaCN /HCN (cyanohydrin formation) and hydrolysed producing aldonic acid.
Theoretically, one isomer of an aldose produces two diastereomeric aldonic acid, however one of
this is obtained in greater yield in practice. The aldonic acid is separated at this stage and
separated acids when heated forms lactone, which when reduced which sodiumamalgam
gives higher aldose.

CN COOH O=C HC=O

HC=O HCOH HCOH HCOH HCOH
O
(HCOH)2 (HCOH)2 (HCOH)2 (HCOH)2
CN/HCN H3O+ Na/Hg (HCOH)2
HCOH HCOH HCOH HC CO2
HCOH
CH2OH CH2OH CH2OH CH2OH CH2OH
a Daldopentose a cyanohydrin a glyconic acid a lactone a Daldohexose

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14. RUFF’S DEGRADATION METHOD
In this method, aldose is oxidised by bromine water to corresponding aldaric acid
(only CHO is oxidised into COOH) and calcium salt of this acid when treated with Fenton’s
reagent (H2O2/Fe2+) the aldose is converted into corresponding lower aldose.
CHO COOH CO2
CHO
CHOH Br2 water CHOH CHOH 2+
Ca salt H2O2/Fe
(CHOH)3
(CHOH)3 (CHOH)3 (CHOH)3
CH2OH
CH2OH CH2OH CH2OH
(Aldopentose)
(Aldohexose)
This method involves oxidative decarboxylation, where CHOH in oxidised to CH=O without
any configurational changes of the other chiral carbons.

4. Disaccharides
Carbohydrates which upon hydrolysis give two molecules of the same or different
monosaccharides are called disaccharides. Their general formula is C12H22O11. The three most
important disaccharides are sucrose, maltose, and lactose. Each one of these on hydrolysis with
either an acid or an enzyme gives two molecules of the same or different monosaccharides as
shown below:

H
C12H22O11  H2O 
 C6H12O6  C6H12O6
Sucrose or invertase Glu cos e Fructrose
H
C12H22O11 + H2O  
 C6H12O6 + C6H12O6
or Maltase
Maltose Glucose Glucose

H
C12H22O11 + H2O  
 C6H12O6 + C6H12O6
or Lactase
Lactose Glucose Galactose
Disaccharides may also be considered to be formed by a condensation reaction between two
molecules of the same or different monosaccharides with the eliminatioin of a molecule of water.
This reaction involves the formation of an acetal from a hemiacetal and an alcohol in which one
of the monosaccharides acts as the hemiacetal while the other acts as the alcohol.

4.1 Maltose

Maltose is another disaccharide, which is made up of two Dglucose units joined together by
glycosidic linkage in such a way that one anomeric OH (C1) is joined with OH (C4) in other unit.
6
6 CH2OH
CH2OH
O H O OH
H 5
H 5
H 4
H 1
4 1 OH H
OH H 2 H
3 2 O 3
OH
H OH H OH

Dglucopyranose Dglucopyranose

Structure of Maltose (D glucopyranose D glucopyranose

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4.2 Sucrose

It is formed by condensation of one molecule of glucose and one molecule of fructose. Unlike
maltose and lactose, it is non-reducing sugar since both glucose (C1 - ) and fructose (C2 - ) are
connected to each other through their reducing centres. Its structure is shown below:

4.1.1 Hydrolysis 6
CH2OH
(Invert Sugar or Invertose). Hydrolysis of sucrose
with hot dilute acid yields D-glucose and D-fructose. 5 O
H H

H H
C12H22O11 + H2O 
 C6H12O6 + C6H12O6
4 1
Sucrose D-glucose D-fructose OH H
[] D = +66.5° [ ]D = +53° [ ]D = –92°  -link
HO 2
Invert Sugar 3
[] D = (+53°) – (–92°) = –39°
H OH O  Glycosidic
Sucrose is dextrorotatory, its specific rotation being linkage
+66.5%, D-glucose is also dextrorotatory, []D = +53°, (Glucose unit)
but D-fructose has a large negative rotation, []D = - CH2OH O  -link
92°. Since D-fructose has a greater specific rotation
than D-glucose, the resulting mixture is
laevorotatory. Because of this the hydrolysis of
sucrose is known as the inversion of sucrose, and the H H OH CH2OH
equimolecular mixture of glucose and fructose is
known is invert sugar or invertose.

OH H
(Fructose unit) Sucrose

5. Polysaccharides

Polysaccharides are formed when a large number (hundreds to even thousands) of

monosaccharide molecules join together with the elimination of water molecule. Thus,
polysaccharides may be regarded as condensation polymers in which the monosaccharides are
joined together by glycosidic linkages. Some important polysaccharides are:

1. Cellulose 2. Starch
3. Glycogen 4. Gums and
5. Pectins

5.1 Starch

It is a polymer of glucose. Its molecular formula is (C6H10O5)n where the value of

n (200 – 1000) varies from source to source. It is the chief food reserve material or storage
polysaccharide of plants and is found mainly in seeds, roots, tubers, etc. Wheat, rice, potatoes,
corn, bananas etc., are rich sources of starch.

Starch is not a single compound but is a mixture of two components – a water soluble
component called amylose (20%) and a water insoluble component called amylopectin (80%).
Both amylose and amylopectin are polymers of -D-glucose.
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Amylose is a linear polymer of -D-glucose. It contains about 200 glucose units which are linked
to one another through -linkage involving C1 of one glucose unit with C4 of the other as shown
below:
C1 – C4 – -linkage

(– Glucose – Glucose – Glucose – Glucose –)n

Linear Polymer

Amylopectin, on the other hand, is a highly branched polymer. It consists of a large number
(several branches) of short chains each containing 20-25 glucose units which are joined together
through -linkages involving C1 of one glucose unit with C4 of the other. The C1 of terminal
glucose unit in each chain is further linked to C6 of the other glucose unit in the next chain
through C1 – C6 -linkage. This gives amylopectin a highly branched structure as shown below.-

C1  C4 -linkage
Glucose  Glucose  Glucose
 C1  C6 -linkage
Glucose  Glucose  Glucose
 C1  C6 -linkage
Glucose  Glucose  Glucose

Hydrolyis: Hydrolysis of starch with hot dilute acids or by enzymes gives dextrins of varying
complexity, maltose and finally D-glucose. Starch does not reduce Tollen’s reagent and Fehling’s
solution.

Uses: It is used as a food. It is encountered daily in the form of potatoes, bread, cakes, rice etc.
It is used in coating and sizing paper to improve the writing qualities. Starch is used to treat
textile fibres before they are woven into cloth so that they can be woven without breaking. It is
used in manufacture of dextrins, glucose and ethyl alcohol. Starch is also used in manufacture
of starch nitrate, which is used as an explosive.

6. Amino Acids

6.1 Introduction and Nomenclature

Amino acids are molecules, which contain two functional groups, one is carboxylic group and
another is amino group. Amino acids are derivatives of carboxylic acids in which one hydrogen
atom of carbon chain is substituted by Amino group.

Amino group may be at , ,  position with respect to carboxylic group

H2N  CH2  COOH Amino acetic acid, or Glycine

CH3  CH (NH2)  COOH  - Amino propionic acid or Alanine

H2N  CH2  CH2 COOH  - Amino propionic acid

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H2N  CH2  (CH2)2  COOH  - Amino butyric acid

Some amino acids contain a second carboxyl group or a potential carboxyl group in the form of
carboxamide: these are called acidic amino acid some contain a second basic group which
may be an amino group these are called basic amino acids.

HOOC  CH2  CH  COOH H2N  CH2  CH2  CH2  CH2  CH  COOH

 
NH2 NH2
Aspartic acid Lysine
(Acidic amino acid) (Basic amino acid)

6.2 Physical Properties and Structure

Although the amino acids are commonly shown as containing an amino group and a carboxyl
group, certain properties are not consistent with this structure.

1. In contrast to amines and carboxylic acids, the amino acids are nonvolatile solids, which melt
at fairly high temperatures.

2. They are insoluble in organic solvents [i.e. non polar solvents] and are highly soluble in
water.

3. Their aqueous solution is neutral.

4. Their aqueous solutions behave like solutions of substances of high dipole moment.

5. Acidity and basicity constants are ridiculously low for - COOH and – NH2 groups

All these properties are quite consistent with a dipolar ion structure for the amino
acids (I)
+
H3N  CHR  COO––
(I)
Amino acid : dipolar ions

In the physical properties melting points, solubility, and high dipole moment are just what would
be expected of such a salt.

The acid base properties also become understandable when it is realized that the measured Ka
actually refers to the acidity of an ammonium ion, RNH3+
+
H3NCHRCOO– + H2O H3O+ + H2NCHRCOO–
[H3O  ][H2NCHRCOO ]
Ka 
[  H3N  CH  RCOO  ]

and Kb actually refers to the basicity of a carboxylate ion, RCOO–

+
H3N  CH  RCOO– + H2O +
H3N  CHR COOH + OH–

[  H3N  CHR  COOH][OH ]

Kb 
[  H3NCHRCOO  ]
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When the solution of an amino acid is made alkaline, the dipolar ion(I) is converted to the anion
(II); the stronger base, hydroxide ion, removes a proton from the ammonium ion and displaces
the weaker base, the amine
+
H3N  CHRCOO– + OH– H2N CHRCOO– + H2O
(I) (II)
Stronger Stronger Weaker Weaker
acid base base acid

When the solution of an amino acid is made acidic; the dipolar ion I is converted into the cation
(III); the stronger acid H3 O , gives up a proton to the carboxylate ion, and displaces the weaker
carboxylic acid.
+
H3N CHRCOO– + H3O+ +
H3N CHRCOOH + H2O
(I) (III)
Stronger Stronger Weaker Weaker
base acid acid base

In summary, the acidic group of a simple amino acid like glycine is  NH 3 not –COOH, and basic
group is –COO- not –NH2.

6.3 Iso Electric Point

What happens when a solution of an amino acid is placed in an electric field depends upon the
acidity or basicity of solution. In quite alkaline solution.
+ +
– H + – H +
H2N-CHRCOO H3N.CHRCOO
– – H3N.CHRCOOH
OH OH
(II) (I) (III)

Anions (II) exceed cations (III), and there is a net migration of amino acid toward the
anode. In quite acidic solution cations (III) are in excess, and there is a net migration of
amino acid towards the cathode. If (II) and (III) are exactly balanced, there is no net
migration; under such conditions any one molecule exists as a positive ion and as a
negative ion for exactly the same amount of time and any small movement in the
direction of one electrode is subsequently cancelled by an equal movement back
towards the other electrode. The hydrogen ion concentration of the solution in which a
particular amino acid does not migrate under the influence of an electric field is called
the isoelectric point of that amino acid.

An amino acid shows its lowest solubility in a solution at the isoelectric point, since
here there is the highest concentration of the dipolar ion. As the solution is made more
alkaline or more acidic, the concentration of one of the more soluble ions, II or III
increases.

If an amino acid has amino group and one carboxyl group, it has two pK values. The
isoelectric point (PI) of this amino acid has the average value of the both pK values.

We take example of glycine.

H3+N  CH2  COOH H3N+  CH2  COO– + H+ …(1)

Conjugated acid (CA) Dipolar Ion (DI)
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BIOMOLECULES , POLYMERS & POC
[D I][H ]
At equilibrium K1 
[CA ]

H3N+  CH2  COO– H2N  CH2  COO– + H+ …(2)

DI Conjugated Base (CB)
[CB][H ]
At equilibrium K 2 
[DI]
[DI][H  ]
[CA] =
K1
K 2 [DI]
[CB] =
[H  ]
At isoelectric point [CA] = [CB]
[DI][[Hi ] K 2 [DI]
 Where [Hi ] = conc. of [H+] at isoelectric point.
K1 [Hi ]

or, [Hi ] 2 = K1 K2
or, 2log [Hi+] = log K1 + log K2
or –2 log (Hi+] = - log k1 – logK2
or 2pHi = pK1 + pK2
pK1  pK 2
or pHi =
2
7. Peptides

As the amino acid molecules contain both basic as well as acidic group it might be expected that
an intermolecular reaction may take place between the carboxyl group of one amino acid and
the amino group of another amino acid, with the elimination of a molecule of water.

R R R R
   
H2N  CH  COOH + H2N  CH  COOH  H2 N  CHCO  NH  CHCOOH

Since the resulting molecule still has a free amino and a carboxyl group, it may react with other
amino acids at either of the ends to give a higher molecular weight linear or condensation
product. Every two amino acids are linked by means of a –CO-NH group, which is commonly
referred as peptide bond. So now we can define a peptides as the amides formed by
interaction between amino groups and carboxyl groups of amino acids.

Depending upon the number of amino acid residues per molecule, they are known as dipeptides,
tripeptides and so on and finally polypeptides.

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7.1 Naming of Polypeptide

A convenient way of representing peptide structures by use of standard abbreviations.

According to convention the N-terminal amino acid residue [having the free amino
group] is written as the left and the C terminal amino acid residue (having the free
carboxyl group) at the right end.

A peptide is named by indicating its sequence of amino acids beginning with the N-terminal
residue.

H2N  CH  CONH  CH  CONH  CH  CONH  CH  CONHCH2 COOH

| | | |
CH3 CH2-OH CH2-C6H5 CH2-CONH2
Alanine SerinePhenylalamine Asparagine glycine

This pentapeptide is called alanyl-sery-phenylalanyl-asparaginyl-glycine or using the common

abbreviations as H-Ala-Ser-phe-Asn-gly-OH. All naturally occurring important peptides, however,
posses a shorter individual name.

7.2 Structure of Poly peptides

To identify the structure of a peptide, the peptide in question is first hydrolysed to its
constituent amino acids, which are separated and identified. The amount of each amino
acid is measured, and hence the number of each kind of amino acid can be calculated.

The next problem is to determine the sequence of the various amino acids constituting
the peptide. This is very difficult task, because there is a large number of possibilities
in which the constituent amino acids may be linked in the peptide, e.g. even is a
dipeptide, having glycine and alanine, the two amino-acids may be present in either of
the two ways.

CH3 CH3
 
H2N – CH2 – CO – NH – CH – COOH H2N – CH – CO – NH – CH2 – COOH
Glycylalanine Alanylaglycine

The two structures differ in the respect that in the first the N-terminal amino acid is
glycine (i.e. the amino group of glycine is free) and C-terminal amino acid is alanine,
while in the latter the N-terminal amino acid is alanine and C-terminal acid is glycine.
Various chemical methods have been developed to remove either of the two terminal
amino acid residues of a polypeptide in a stepwise manner and hence the arrangement
of the various amino acids in a polypeptide can be established.

8. Polymers

8.1 Introduction

Sit quietly and think about your activities today from the morning. You wake up in the morning,
You want to brush your teeth. You fetch your toothpaste. The tube is made up of a polymer. Your
brush is made up of a polymer. When you want to rinse your mouth, you open your
plastic(polymer) tap. The pipe lines used to bring water to your tap is made of PVC(polymer).
Skip it. You start preparing your break fast. You take a non-stick tawa. Non-stick? What does
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BIOMOLECULES , POLYMERS & POC
that mean? What is it made of? It is poly tetrafluoro ethylene abbreviated as teflon, a polymer.
See, how polymers play an important role in our daily life from dawn to dusk. The molded chair in
which you are sitting is a polymer. The pen with which I'm writing this is a polymer. Want to know
more about polymers? Read further.

Polymers can be called as macromolecules. Macromolecules can be considered as an

association of small molecules to give a big molecule. Macromolecules can be man-made, too.
The first syntheses were aimed at making substitutes for the natural macromolecules, rubber and
silk; but a vast technology has grown up that now produces hundreds of substances that have no
natural counterparts. Synthetic macromolecular compounds include: elastomers, which have the
particular kind of elasticity characteristic of rubber; fibers, long, thin and threadlike, with the great
strength along the fiber that characterizes cotton, wool, and silk; and plastics, which can be
extruded as sheets or pipes, painted on surfaces, or molded to form countless objects. We wear
these manmade materials, eat and drink from them, sleep between them, sit and stand on them;
turn knobs, pull switches, and grasp handles made of them; with their help we hear sounds and
see sights remote from us in time and space; we live in houses and move about in vehicles that
are increasingly made of them.

8.2 Polymers and polymerization

Macromolecules, both natural and man-made, owe their great size to the fact that they are
polymers (Greek: many parts); that is, each one is made up of a great many simpler units —
identical to each other or at least chemically similar — joined together in a regular way. They are
formed by a process we touched on earlier: polymerization, the joining together of many small
molecules to form very large molecules. The simple compounds from which polymers are made
are called monomers.

Polymers are formed in two general ways.

a) In chain-reaction polymerization, there is a series of reactions each of which consumes a

reactive particle and produces another, similar particle; each individual reaction thus depends
upon the previous one. The reactive particles can be free radicals, cations, or anions. A
typical example is the polymerization of ethylene. Here the chain-carrying particles are free
radicals, each of which adds to a monomer molecule to form a new, bigger free radical.
CH 2  CH 2
Rad. + CH2 = CH2  RadCH2CH2    RadCH2CH2CH2CH2  etc.

b) In step reaction polymerization, there is a series of reactions each of which is essentially

independent of the preceding one; a polymer is formed simply because the monomer
happens to undergo reaction at more than one functional group. A diol, for example, reacts
with a dicarboxylic acid to form an ester; but each moiety of the simple ester still contains a
group that can react to generate another ester linkage and hence a larger molecule, which
itself can react further, and so on.

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HOCH2CH2OH + HOOC COOH

1,2-Ethanediol Terephthalic acid

HOCH2CH – O – C – – C – OH
|| ||
O O
HOCH2CH2OH

HOCH2CH2 – O – C – – C – O – CH2CH2OH
|| ||
O O
p-C6H4(COOH)2

HO– C – – C – O – CH2CH2 – O – C – – C – O – CH2CH2OH

|| || || ||
O O O O

a) Free-radical vinyl polymerization: In we discussed briefly the polymerization of ethylene and

substituted ethylenes under conditions where free radicals are generated — typically in the
presence of small amounts of an initiator, such as a peroxide. Reaction occurs.
initiator
nCH2 = CH     – CH2CHCH 2CHCH2CHCH2CH –
| | | | |
G G G G G

Vinyl monomer or (– CH2CH –)n

|
G
Polymer

At the doubly bonded carbons — the vinyl groups — and is called vinyl polymerization. A
wide variety of unsaturated monomers may be used, to yield polymers with different pendant
groups (G) attached to the polymer backbone. For example.

CH2 = CH  – CH2 – CH – CH2 – CH – CH2 – CH –

| | | |
Cl Cl Cl Cl
Vinyl chloride Poly (vinyl chloride)
(PVC)

CH2 = CH  CH2 – CH – CH2 – CH – CH2 – CH – CH2 – CH –

| | | | |
CN CN CN CN CN
Acrylonitrile Polyacrylonitrile
(Orlon)

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 BIOMOLECULES , POLYMERS & POC
CH2 = CH  CH2 – CH – CH2 – CH – CH2 – CH –
| | | |
C6H5 C6H5 C6H5 C6H5
Styrene Polystyrene

b) Copolymerization: So far, we have discussed only polymerisation of a single monomeric

compound to form a homopolymer, a polymer made up — except, of course, at the two ends of
the long molecule — of identical units.

Now, if a mixture of two (or more) monomers is allowed to undergo polymerization, there is
obtained a copolymer a polymer that contains two (or more) kinds of monomeric units in the
same molecule. For example:

CH3 CH3
| |
initiator
CH2 = CH + CH2 = C      – CH2 – CH – CH2 – C –
| | | |
Ph COOCH3 Ph COOCH3
Styrene Methyl methacrylate Polystyrene (co-methyl methacrylate)

Through copolymerization there can be made materials with different properties than those of
either homopolymer, and thus another dimension is added to the technology. Consider, for
example, styrene. Polymerized alone, it gives a good electric insulator that is molded into parts
for radios, television sets, and automobiles. Copolymerization with butadiene (30%) adds
toughness; with acrylonitrile (20-30%) increases resistance to impact and to hydrocarbon; with
maleic anhyride yeilds a material that, on hydrolysis, is water-soluble, and is used as a
dispersant and sizing agent. The copolymer in which butadiene predominates (75%) butadiene,
25% styrene) is an elastomer, and since World War II has been the principal rubber substitute
manufactured in the United States.

Copolymers can be made not just from two different monomers but from three, four, or even
more. They can be made not only by free-radical chain reactions, but by any of the
polymerization methods we shall take up; ionic, coordination, or step-reaction. The monomer
units may be distributed in various ways, depending on the technique used. As we have seen,
they may alternate along a chain, either randomly or with varying degrees of regularity. In block
copolymers sections made up of one monomer alternate with sections of another:

— M1M1M1M1M1 – M2M2M2M2 — Block copolymer

If graft copolymers, a branch of one kind is grafted to a chain of another kind:

— M1M1M1M1M1M1M1 —
|
M2M2M2M2

Fibres are long thin, threadlike bits of material that are characterized by great tensile (pulling)
strength in the direction of the fiber. The natural fibres – cotton, wool, silk – are typical. Fibres
are twisted into threads, which can then be woven into cloth, or embedded in plastic material to

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 BIOMOLECULES , POLYMERS & POC
impart strength. The tensile strength can be enormous, some synthetic fibres rivaling – on a
weight basis – steel.

The gross characteristics of fibres are reflected on the molecular level – the molecules, too, are
long, thin, and threadlike. Furthermore, and most essential, they lie stretched out alongside each
other, lined up in the direction of the fiber. The strength of the fiber resides, ultimately, in the
strength of the chemical bonds of the polymer chains. The lining-up is brought about by drawing
– stretching — the return to random looping and coiling is overcome by strong intermolecular
attractions. In a fiber, enthalpy wins out over entropy. This high degree of molecular orientation is
usually — although not always — accompanied by appreciable crystallinity.

An elastomer possesses the high degree of elasticity that is characteristic of rubber: it can be
greatly deformed — stretched to eight times its original length, for example — and yet return to
its original shape. Here, as in fibres, the molecules are long and thin; as in fibres, they become
lined up when the material is stretched. The big difference is this: when the stretching force is
removed, the molecular chains of an elastomer do not remain extended and aligned but return
to their original random conformations favored by entropy. They do not remain aligned because
the intermolecular forces necessary to hold them that way are weaker than in a fiber. In general,
elastomers do not contain highly polar groups or sites for hydrogen bonding; the extended chains
do not fit together well enough for Vander Waals forces to do the job. In an elastomer entropy
beats enthalpy.
One further requirement the long chains of an elastomer must be connected to each
other by occasional cross – links: enough of them to prevent slipping of molecules past
one another; not so many as to deprive the chains of the flexibility that is need for
ready extension and return to randomness.

Natural rubber illustrates these structural requirements of an elastomer; long flexible chains;
weak intermoecular forces and occasional cross – linking. Rubber is cis 1,4-polyisoprene . With
no highly polar substituents, intermolecular attraction is largely limited to van der Waals forces.
But these are weak because of the all – cis configuration about the double bond. Figure below
compares the extended chains of rubber with those of its trans stereoisomer. As we can see, the
trans configuration permits highly regular zig – zags that fit together well; the cis configuration
does not. The all-trans stereoisomer occurs naturally as gutta percha; it is highly crystalline and
non-elastic.

(a)

(b)

Extended chains of (a) natural rubber, cis-1,4 –polyisoprene, and of (b) gutta
percha, its trans stereoiosmer.

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BIOMOLECULES , POLYMERS & POC
Chief among the synthetic elastomers is SBR, a copolymer of butadiene (75%) and
styrene (25%) produced under free-radical conditions; it competes with natural rubber
in the main use of elastomers, the making of automobile tires. All-cis polybutadiene and
polyisoprene can be made by Ziegler – Natta polymerization.

An elastomer that is entirely or mostly polydiene is, of course, highly unsaturated. All that is
required of an elastomer, however, is enough unsaturation to permit cross-linking. In making
butyl rubber for example, only 5% of isoprene is copolymerized with isobutylene.

Some Important Polymers:

a) Natural Rubber: Natural rubber is an addition polymer of isoprene (2-methyl-1,3-butadiene)

Rubber has an average chain length of 5000 monomer units of isoprene.
The rubber in which the arrangement of carbon chain is trans with respect to the double bond
is known as Gutta Percha and this is the natural rubber obtained from bark of various trees.
Natural rubber is sticky material. This disadvantage is removed by 'VULCANISATION' which
involves addition of sulphur to rubber and heating the mixture. sulphur forms short chains of
sulphur atoms that link two hydrocarbon (isoprene) units together.

CH 3 CH 3

----CH—C=CH—CH 2—CH—C=CH—CH 2----

S
S

----CH—C=CH—CH 2—CH 2—C=CH—CH—CH------

CH 3 CH 3

When tension is applied the chains can strengthen out but they cannot slip past each other
because of sulphur bridges. Thus rubber can be stretched only to a certain extent and
hydrocarbon chains have the tendency to regain their shape when tension is removed.
Vulcanised rubber is thus stronger and less sticky than the natural rubber.

b) Synthetic rubber: (Polychloroprene) or Neoprene) It is obtained by free radical

polymerisation of chloroprene in
Cl Cl

nCH 2=C—CH=CH 2  (–CH 2—C=CH—CH 2—)n

Neoprene

it is a thermoplastic and need not to be vulcanised. It is a good general purpose rubber and
superior to natural rubber as it is resistant to the reaction of aire, heat, light chemicals, alkalis
and acids below 50% strength. It is used for making transmission belts, printing rolls and
flexible tubing employed for conveyence of oil and petrol.

c) Buna rubbers: Butadiene polymerises in the presence of sodium to give a rubber substitute
viz. BuNa. It is of two types

i) Buna - N or GRA: it is synthetic rubber obtained by copolymerisation of one part of acryl

nitrile and two parts of butadiene.
22 CLASS XII CHEMISTRY
 BIOMOLECULES , POLYMERS & POC
nCH 2=CH—CH=CH 2 + nCH 2=CH  —CH2—CH=CH—CH 2—CH 2—CH

CN BUNA-S CN n

It is more rigid responds less to heat and very resistant to swelling action of petorol, oils
and other organic solvents.

ii) Buna -S or GRS (General purpose Styrene rubber): It is a copolymer of three moles of
butadiene and one mole of styrene\ and is an elastomer. It is obtained as a result of free
radical copolymerisation of its monomers.

nC 6H 5CH=CH 2 + nCH 2=CH—CH=CH 2 [–CH 2–CH=CH–CH 2–CH–CH 2–]n

C 6H 5
BUNA-S

It is generally compounded with carbon black and vulcanised with sulphur. It is extremely
resistant to wear and tear and finds use in manufacture of tyres and other mechanical
rubber goods.

d) Teflon: It is polymer of tetrafluorethylene (F2C=CF2) which on polymerisation gives Telfon.

870 1020K
nCF2=CF2     (—CF2—CF2—)n

It is thermoplastic polymer with a high softening point (600K). It is very tough and difficult to
work. It is inert to most chemicals except fluorine and molten alkali metals. It withstands high
temperatures. Its electrical properties make it an ideal insulating material for high frequency
installation.

e) Nylon -66: It is a polymer resin. It is a condensation polymer formed by reaction between

adipic acid and hexamethylene diamine. Both monomer units consist of 6 carbon atoms and
therefore named nylon -66.

O H
|| |
H2O
HO  C  (CH2 )4  C OH  H  N (CH2 )6  NH2  

 O O H 
 || || | 
  C (CH2 )4  C N (CH2 )6  NH    
 
 
Nylon 66
( A condensati on copolymer)

It is thermoplastic polymer when extruded above its melting point (536 K) through spinneret,
it gives nylon fiber which is extremely tough and resistant to friction. It possess greater tensile
strength, elasticity and lusture than any natural fiber. It is chemically inert and is fabricated
into sheet, bristles and textile fibres.

f) Nylon 6 or Perolon - L: A polyamide is prepared by prolonged heating of caprolactam at 530 -

540 K.

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 BIOMOLECULES , POLYMERS & POC
NH  
(CH 2)5 540
 K      ( CH 2 ) 5 C  NH  ( CH ) 5 C  NH    
 || || 
C=O  O O 
Nylon  6

The fiber is practically identical to Nylon in properties

9. Practical Organic Chemistry

9.1 Introduction

\This lesson is an extremely useful exercise for the structure elucidation of newly synthesized
organic molecules. The technique involved is elemental detection, determination of functional
groups, number of such functional groups, determination of molecular formula, preparation of
derivatives and determining their melting and boiling points. All these steps are to be followed in the
same sequence, as one leads to another.
The ultimate portion of the lesson deals with the procedure for separating a mixture of organic
compounds (containing monofunctional groups) into its constituents in pure form, so that the above
procedure can be carried out effectively.

9.2 Qualitative Analysis

Qualitative analysis of an organic compound involves following operations.

(i) Preliminary examination:
(A) Physical state (B) Colour (C) Odour (D) Ignition test (e) Solubility test
(ii) Detection of elements
(iii) Detection of functional groups
(iv) Determination of melting or boiling point and
(v) Preparation of derivatives.
9.2.2 Detection of Elements
The elements generally present in organic compounds are carbon, hydrogen and oxygen. The
detection of these elements in the organic compounds is not essential. Organic compounds also
contain nitrogen, halogens, phosphorus and sulphur, in addition to these elements.
Thus, detection of elements basically refers to nitrogen, halogens, phosphorous & sulphur.
Detection of Carbon and Hydrogen
The organic compound is mixed with an equal amount of dry copper oxide and strongly heated. The
carbon present in the compound is oxidised to carbon dioxide (turns limewater milky) and hydrogen
to water (turns anhydrous copper sulphate blue).

C + 2CuO  CO2 + 2Cu

2H + CuO  H2O + Cu
CO2 + Ca(OH)2  CaCO3 + H2O
limewater white

CuSO4H2O + 4H2O  CuSO45H2O

white blue
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Lassaigne’s test
Nitrogen, sulphur and halogens in an organic compound are detected by Lassaigne’s test through
Lassaigne’s extract. Organic compounds contain these elements mostly linked through covalent bonds.
In order to make them free, we convert them into ionic form by treating the compound with sodium. The
ionic compound formed are watersoluble and releases the element in ionic form, which is easy to
detect.

(A) Preparation of Lassaigne’s Extract

A small piece of dry sodium metal is heated gently in a fusion tube till it melts to a shining
globule. Then, a small amount of organic substance is added and the tube is heated strongly till it
becomes red hot. The red hot tube is plunged into distilled water contained in a china dish. The
fusion tube should break into pieces on adding to water. If it is not broken, it is broken using a
glass rod. Then the solution is boiled for some time. It is then cooled and filtered. The filtrate is
known as sodium extract or Lassaigne’s extract.
Sodium reacts with elements of the organic compound to give following reactions.
C + N + Na  NaCN
S + 2Na  Na2S
X + Na  NaX (where X = Cl, Br or I)
When nitrogen and sulphur both are present in the organic compound, then sodium thiocynate is
formed.
Na + C + N + S  NaSCN
All the sodium salts being soluble in water, can be easily detected.
Detection of Nitrogen
If the organic compound contains nitrogen, the sodium fusion extract will contain sodium cyanide
(NaCN). A small portion of the extract is boiled with ferrous sulphate solution and acidified with
dilute sulphuric acid. A blue precipitate of Prussian blue (ferric ferrocyanide) confirms the
presence of nitrogen.
2NaCN + FeSO4  Fe(CN)2 + Na2SO4
Fe(CN)2 + 4NaCN  Na4[Fe(CN)6]
(excess)
Oxidised by
FeSO4    
 Fe2(SO4)3
H 2SO 4

3Na4[Fe(CN)6] + 2Fe2(SO4)3  Fe4[Fe(CN)6]3 + 6Na2SO4

Prussian blue
If the organic compound contains sulphur along with nitrogen and the sodium, present is in
insufficient amount then sodium thiocynate is formed, which gives blood red colouration by
reaction with ferric ions.
3NaSCN + Fe3+  [Fe(SCN)3] + 3Na+
Blood red colour
However, the absence of blood red colouration does not necessarily mean that sulphur is absent
in the organic compound because NaCNS combines with Na to give NaCN and Na2S.
NaSCN + HCl  HSCN + NaCl
4HSCN + Co(NO3)2  H2[Co(SCN)4] + 2HNO3
Blue colour
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Detection of Sulphur
If the organic compound contains sulphur, the sodium fusion extract will contain sodium sulphide.
It is divided into two portions and following tests are performed.

Sodium Nitroprusside Test:

Add freshly prepared sodium nitroprusside solution to one portion. A deep violet colour confirms
the presence of sulphur.

Na 2 S  Na 2 [Fe(CN) 5 NO]  Na 4 [Fe(CN) 5 NOS]

Violet colour

Lead Acetate Test:

Acidify the second portion with acetic acid and then add lead acetate solution. A black precipitate
of lead sulphide confirms the presence of sulphur.

Na 2 S  (CH3 COO) 2 Pb  PbS   2CH 3 COONa

lead acetate black ppt.

Detection of Halogens
If the organic compound contains halogen, the sodium fusion extract will contain sodium halide.
The sodium fusion extract is boiled with dilute nitric acid to decompose sodium cyanide or
sodium sulphide, (if present) otherwise a white precipitate of silver cyanide or silver sulphide will
be formed even in the absence of halogen. The solution is then cooled and silver nitrate solution
is added. The characteristic precipitate confirms the presence of a halide.
NaX  AgNO 3  AgX   NaNO 3
(A) White precipitate, soluble in aqueous ammonia indicates chlorine.
(b) Light yellow precipitate, sparingly soluble in aqueous ammonia indicates bromine.
(c) Pale yellow precipitate, insoluble in aqueous ammonia indicates iodine.

Detection of Phosphorus
The organic compound containing phosphorus is fused with sodium peroxide and extracted with
water. The aqueous solution is boiled with concentrated nitric acid and ammonium molybdate is
added. A canary yellow precipitate indicates the presence of phosphorus.
9.2.3 Detection of Functional groups

Detection of functional groups is an important step in the analysis of organic compounds.

It entirely depends on the correct determination of the constituent elements.

1. Tests for Carboxylic Acid Group

(i) Litmus test: Place a small quantity of the organic compound or its aqueous solution on a
piece of moist blue litmus paper. If the litmus paper turns red, carboxylic acid group may be
present.
(ii) Sodium bicarbonate test: Add a small quantity of the organic compound to sodium
bicarbonate solution taken in a testtube. Compound dissolves with brisk effervescences.
RCOOH + NaHCO3  RCOONa + H2O + CO2 
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(iii) Take a small quantity of the organic compound and add some alcohol in a testtube. Add a
few drops of conc. sulphuric acid and warm on a water bath, a fruity smell indicates the
formation of an ester.
H2SO 4
RCOOH  R OH   RCOOR H 2 O
Ester

2. Tests for Aldehyde Group

(i) Schiff’s test: Take small amount of Schiff’s reagent in a testtube and shake with organic
compound (do not heat). A pink colour appears instantaneously.
(ii) Fehling’s test: Mix equal volumes of Fehling’s (A) and Fehling’s (B) solution in a testtube.
Add a small amount of the organic compound and boil for some time. A red precipitate of
Cu2O is obtained.
RCHO  2CuO  RCOOH  Cu 2 O 
Re d ppt.
(iii) Tollen’s test: Add few drops of Tollen’s reagent ppt. to a small quantity of the organic
compound and heat on a water bath. A shining silver mirror is formed on the inner walls of
testtube.
RCHO  2 [ Ag(NH 3 ) 2 ]OH  H 2 O  RCOONH 4  NH 3  2NH 4 OH  2Ag 
Tollen ' s reagent Silver mirror

(iv) Benedict’s test: Take small amount of Benedict’s reagent in a testtube. Add a few ml of
the organic compound (or a solution prepared in alcohol or water). Heat the mixture to
boiling. Formation of red precipitate indicates the presence of aldehydic group.
RCHO  2Cu(OH) 2  NaOH  Cu 2 O  RCOO  Na   3H2 O

3. Tests for Ketone Group

(i) Ketones, unlike aldehydes, do not restore the pink colour of Schiff’s reagent nor do they
reduce Fehling’s solution or ammoniacal silver nitrate solution. However, they form yellow
or red crystalline precipitate with 2,4dinitro phenylhydrazine and also with sodium
bisulphite reagent. This test should be conduct only after the confirmation of absence of
aldehydes.

NO2 NO2
R R
C=O + H2NHN NO2  C=NHN NO2
R R
(2,4 DNP)

Ketones add on sodium hydrogen sulphite to form crystalline bisulphite compounds.

R R OH
C=O + NaHSO3  C
R R SO3Na
(Bisulphite addition
compound)

(ii) Sodium nitroprusside test: Treat some organic compound with few drops of
freshly prepared solution of sodium nitroprusside followed by excess of NaOH solution. A
winered colour is obtained.

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4. Tests for Phenol Group

(i) Litmus test: Place a trace of the organic compound on the moist blue litmus paper.
It turns red.
(ii) Neutral FeCl3 test: When phenols are treated with neutral ferric chloride solution, they form
coloured complexes. The colour of the complex may be violet, red, blue
or green. This is a characteristic reaction of compounds having enolic group (=COH). All
stable enols respond to this test.
With relatively milder oxidizing agents such as ferric chloride (Fe3+), a resonance stabilized
phenoxyl radical is formed. This radical soon undergoes dimerization, which may take place
by orthoortho, orthopara, parapara coupling.

OH O O O O
H H
+ Fe3+    
H

+ Fe+2 + H+

O O O
H H H
O
+ +O O
H
H H

The phenoxyl radicals are highly coloured and therefore, products are also coloured.
(iii) Aniline Dye test: Dissolve a little aniline in dilute hydrochloric acid, cool in
icecold water and add aqueous solution of sodium nitrite dropwise. To this cold
solution, add organic compound already dissolved in sodium hydroxide solution.
A red or orange precipitate is obtained.

NaNO 2  HCl  HNO 2  NaCl

This test is applicable for the detection of small quantities of phenols with the para position
free.

(iv) Phthalein test (Fluorescein test) : Heat some organic compound and phthalic anhydride
with a few drops of concentrated sulphuric acid in a testtube. Pour the heated mixture into
water taken in a beaker and then add sodium hydroxide solution, till it became alkaline. A
beautiful pink or purple colour appears.

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OH
OH
C
C=O H2SO4
+ H2O OH
O C O
O C O OH

ONa+
2NaOH
C
O
O=CONa+
(Pink or purple)

(v) Bromine water test: Take aqueous or alcoholic solution of the organic compound in a
testtube. Add excess of bromine water. A yellowish white precipitate is obtained.
OH OH
Br Br
+ 3Br2 

Phenol
Br
(2,4,6tribromophenol)

(vi) Ceric ammonium nitrate test: Add few drops of the ceric ammonium nitrate to
hot aqueous solution of the organic compound. A green or brown precipitate
is obtained.
(NH 4 ) 2 [Ce(NO 3 ) 6 ]  2C 6H 5 OH  [Ce(NO 3 ) 4 (C 6 H5 OH) 2 ]  2NH 4NO 3
Phenol Green or brown ppt.

(vii) Liebermann’s test: Take a small amount of the compound and fuse with a
few crystals of NaNO2 in a testtube. Cool the testtube and add some concentrated H2SO4.
A deep green colour is obtained and when poured into large excess of water, green
colour changes to red. When a little NaOH solution is added to the aqueous solution, the
solution becomes deep blue coloured.

NaNO2 + H2SO4 Tautomerize

HO HO N=O O NOH

(Green colour)

Phenol NaOH
H2SO4
O N OH O N ONa+
+
Indophenol (red) Indophenol salt (blue)

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5. Tests for Alcohol Group
Alcohols may be considered as neutral compounds. They are soluble in water or dioxane.
(i) Sodium test: Take some organic compound in a testtube. Add a thin slice of sodium metal
to it. A brisk effervescence due to the evolution of hydrogen takes place. (Organic
compound should be free from water).
2ROH  2Na  2RO Na   H2 
(ii) Ester test: Warm the given liquid with acetic acid in presence of sulphuric acid.
A fragrant fruity smell indicates the formation of ester.
H2SO 4
ROH  CH3 COOH   CH 3 CO 2R  H2 O
Alcohols give crystalline esters with 3,5dinitrobenzoyl chloride. These esters have sharp
melting points and can be used for testing a given alcohol.
NO2 NO2
ROH + ClC ROC + HCl
O NO2 O NO2
(iii) Oxidation test: Take some organic compound in a test tube, add to it K2Cr2O7 solution and
concentrated H2SO4. Heat the testtube after fitting a delivery tube. The distillate is passed
into another testtube containing water. The solution becomes green coloured. Test the
aqueous solution of the distillate for carboxylic acid group. A positive test indicates the
presence of primary alcoholic group in the given compound.
[O ]
RCH2 OH  RCO 2 H  H 2 O
(iv) Ceric ammonium nitrate test: Shake a few drops of ceric ammonium nitrate with
the organic compound. A red colour is produced. This test is useful only when the
compound contains less than 10 carbon atoms per molecule.
2ROH  (NH 4 ) 2 [Ce(NO 3 ) 6 ]  [Ce(NO 3 ) 4 (ROH) 2 ]  2NH 4 NO 3

Distinction between primary, secondary and tertiary alcohols

Lucas test: Add some amount of alcohol to 2 ml of Lucas reagent (anhydrous ZnCl2 +
concentrated HCl) in a testtube. Shake the mixture and allow it to stand at room temperature. If
a cloudy precipitate of alkyl chloride is obtained immediately then it is a tertiary alcohol, if
obtained within 5 minutes then it is a secondary alcohol, while
no cloudy precipitate even after long standing means it is a primary alcohol. This test is
applicable for alcohols with less than 6 carbon atoms.
+  
RO…..ZnCl2  R

ROH + ZnCl2 Cl
 RCl
+ 
[Zn(OH)Cl2] Cloudy ppt.
H
6. Tests for Primary Amines (NH2)
(i) Carbylamine test: Heat the organic compound with alcoholic KOH and chloroform in a
testtube. A highly offensive smell is evolved due to the formation of isocyanides.

RNH2 + CHCl3 + 3KOH RN C + 3KCl + 3H2O

This test is applicable for aliphatic and aromatic primary amines but not for 2° and
3° amines.
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(ii) Dye test: This test is applicable only for aromatic primary amines. Dissolve a small amount
of the organic compound in dilute HCl. Cool it in icecold water bath. Add cold solution of
sodium nitrite with constant stirring and then alkaline naphthol solution. An orangered
dye is obtained.

7. Tests for Secondary Amines (NH)

Liebermann’s nitroso test:
Dissolve some organic compound concentrated HCl and then add small amount of
water. Cool the solution in icecold water bath and then add cold dilute NaNO2 solution.
A yellow oily emulsion is produced. Take above emulsion in a test tube and add phenol and
concentrated H2SO4 to it. A green colour appears. Addition of water changes
green colour to red, which changes to deep blue on adding NaOH solution.

8. Tests for Nitro Group

(i) Reduction test: Take a small amount of the organic compound in a testtube. Add a few ml
of concentrated hydrochloric acid and one or two pieces of granulated zinc or tin. Heat the
mixture gently for few minutes. Decant the clear liquid into a testtube. Cool it in icecold
water bath and then add cold dilute solution of sodium nitrite. Pour this cold solution into an
alkaline solution of naphthol. An orangered dye is obtained. This test is applicable only
to aromatic nitro compounds.

Zn  2HCl  ZnCl 2  2[H]

C 6 H5 NO 2  6[H]  C 6 H5 NH 2  2H 2 O

NaNO 2  HCl  HNO 2  NaCl

C 6 H5 NH 2  HNO 2  HCl  C 6 H5 N2 Cl   2H 2 O

(ii) Mulliken’s test: Take a small amount of the organic compound in a testtube. Add a few ml
of water or alcohol, 1 ml of calcium chloride or ammonium chloride solution and then a pinch
of zinc dust. Boil the mixture for few minutes. Cool and then filter. Treat this filtrate with
ammoniacal silver nitrate solution. A grey or black precipitate is obtained.

Zn + 2H2O  Zn(OH)2 + 2[H]

C6H5NO2 + 4[H]  C6H5NHOH + H2O
C6H5NHOH + Ag2O  C6H5NO + H2O + 2Ag 
Grey or black ppt.
This test is applicable for aliphatic as well as aromatic nitro compounds.
9.3 Quantative Analysis
After determining the elements present in the organic compound, the subsequent step is to find out
the percentages of elements in the compound. The methods used for determining the percentage of
elements involve combustion, oxidation and precipitation etc. of an organic compound such that they
are converted into inorganic compounds, which can be easily estimated by gravimetric or volumetric
techniques.
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9. 3.1 ESTIMATION OF CARBON AND HYDROGEN

Liebig’s Combustion Method

A known mass of the organic compound is heated in a current of dry oxygen
(free from CO2) in the presence of cupric oxide till all the carbon is oxidised to carbon dioxide and
all the oxygen is oxidised to water.

 y
CxHy +  x   O2  xCO2 + y/2 H2O
 4

Oxidised copper spiral

dry O2 ............
.

Boat with Copper Guard tube

organic Oxidised
substance

Calcium chloride tube KOH tube

Figure 1

Water is absorbed in a previously weighed Utube containing anhydrous calcium chloride or

anhydrous magnesium perchlorate. Carbon dioxide is absorbed in a previously weighed Utube
containing a strong solution of potassium hydroxide or ascarite (NaOH + CaO). The weights of
carbon dioxide and water thus formed are determined and the amounts of carbon and hydrogen
in the organic compound can be calculated as

Mass of CO 2 formed
Moles of CO2 formed = = Moles of C in CO2
44
= Moles of C in organic compound
Moles of CO 2 formed
 Mass of carbon in organic compound =  12
44
12 Mass of CO 2 formed
 Percentage of carbon in organic compound =   100
44 Mass of organic compound

Mass of H 2 O formed
Moles of H2O formed =
18
Mass of H 2 O formed
Moles of H in H2O =  2 = Moles of H in the organic compound.
18
Mass of H 2 O formed  2  1
Mass of hydrogen in the organic compound =
18
2 Mass of H2 O formed
 Percentage of hydrogen in organic compound =   100
18 Mass of organic compound

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9. 3.2 ESTIMATION OF NITROGEN
Nitrogen can be estimated either by Dumas’ method or Kjeldahl’s method.

Duma’s Method
Known mass of an organic compound is heated with cupric oxide in an atmosphere of carbon
dioxide. The carbon and the hydrogen get oxidised to carbon dioxide and water while the nitrogen is set
free. Traces of oxides of nitrogen, which may be formed in some cases are reduced to elemental
nitrogen by passing over heated copper spiral. The gaseous mixture is collected over an aqueous
solution of potassium hydroxide. CO2 is absorbed by the caustic potash solution while H2O condenses
and nitrogen is collected by downward displacement of KOH solution.
The volume of nitrogen is measured and this is equivalent to the nitrogen present in the compound. The
volume of nitrogen is reduced to STP, its weight calculated and from this the percentage of nitrogen
present in the organic compound is estimated.
The following reactions take place during Duma’s process.
C + 2CuO  CO2 + 2Cu ; 2H + CuO  H2O + Cu
2N + CuO  N2 + Oxides of nitrogen

Oxides of nitrogen + Cu  CuO + N2

Nitrogen
CuO + Organic Copper
compound Coarse CuO gauze KOH solution
compound
CuO Gauze
CO2

Furnace Nitrometer

Mercury
Seal

Figure 2. Estimation of nitrogen by Duma’s method

Let the mass of organic compound = w g,

Volume of nitrogen collected = V cm3,
Pressure of moist N2 = P mm of Hg,
Room temperature = t°C,
Aqueous tension at t°C = a mm of Hg,
 Pressure of dry nitrogen = (P  a) mm of Hg,
Let us first convert the volume of nitrogen at given temperature & pressure to the volume of N2 at
STP.
PN2  VN2 = n N2  RT

(P  a)  V  10 3
n N2 
760  0.0821 ( 273  t )
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(P  a)  V  10 3  22.4
 Volume of N2 at STP = = x L (say)
760  0.0821 (273  t )
Now, 22.4 L of N2 at STP weigh = 28 g
 28 
 x L of N2 at STP will weigh =   x g
 22. 4 
Mass of nitrogen 28 x  100
Percentage of nitrogen =  100 =
Mass of organic compound 22.4  w

Kjeldahl’s Method
This method is simpler and more convenient than Duma’s method. This method is largely used
for the estimation of nitrogen in food stuffs, drugs, fertilizers and many other organic compounds.
However, this method cannot be used for
(i) organic compounds containing nitrogen in the ring such as pyridine, quinoline etc.
(ii) organic compounds containing nitro (NO2) and diazo (N=N) groups.

Principle: A known weight of the organic compound is heated with concentrated H2SO4 so that
nitrogen is quantitatively converted into ammonium sulphate. The solution is then heated with excess of
sodium hydroxide. The ammonia gas evolved is passed into a known but excess volume of standard
acid (HCl or H2SO4). The acid left unused is estimated by titrating the solution with standard alkali. From
the amount of acid left unused, the amount of acid used for neutralization of ammonia can be calculated.
From this, percentage of nitrogen can be calculated. The chemical reactions involved are
Conc . H SO
2 4
C, H, S    
  CO2 + H2O + SO2
(From organic compound)

Conc . H SO
2 4
N    
  (NH4)2SO4
(From organic compound) Ammonium sulphate

(NH4)2SO4 + 2NaOH  Na2SO4 + 2NH3 + 2H2O

2NH3 + H2SO4  (NH4)2SO4
(n = 1)
H2SO4 + 2NaOH  Na2SO4 + 2H2O

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NH3 + Steam

Kjeldahl Trap

Water

Kjeldahl’s flask

Substance + conc. Kjeldahlised

H2SO4 + K2SO4 + CuSO4 liquid + NaOH
in excess Water

Known volume
of standard acid

Figure 3. Estimation of nitrogen by Kjeldahl’s method.

Let the mass of organic compound = w g,
Total volume of standard acid taken = V1 cm3,
Normality of acid = N1
Now, the excess acid after dilution is titrated against standard alkali.
Volume of standard alkali used for neutralization of unused acid = V2 cm3,
Normality of standard alkali = N2,
Equivalents of unused acid = Equivalents of alkali = N2V2  103
Initial equivalents of acid = N1V1  103
Equivalents of acid consumed by NH3 = (N1V1  N2V2)103 = Equivalents of NH3 reacted.
Moles of NH3 reacted = (N1V1 N2V2)  103
Moles of NH3 liberated = (N1V1  N2V2)  103 = Moles of nitrogen in NH3
= Moles of nitrogen in organic compound.
Mass of nitrogen in the organic compound = (N1V1  N2V2)  103  14
Mass of nitrogen
Percentage of nitrogen =  100
Mass of organic compound

(N1V1  N 2 V2 )  10 3  14 1.4 (N1 V1  N2 V2 )

=  100 =
w w
where V1 and V2 are the volume of standard acid and alkali respectively, in cm3.
9.3.3 ESTIMATION OF HALOGENS
Carius Method
In this method, a known mass of the organic substance is heated with fuming nitric acid in the
presence of silver nitrate in a special sealed tube known as Carius tube. Carbon, hydrogen or
sulphur present in the compound will be oxidised to CO2, H2O and H2SO4 respectively. The
halogen forms a precipitate of silver halide (AgX). The precipitate is filtered, washed, dried and
weighed.

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3 HNO
C + 2O   CO2
3 HNO
2H + O   H2O
3 HNO
S + H2O + 3O   H2SO4
X + AgNO3  AgX 
(halogen)

Carius tube Iron tube

Organic
substance Glass stopper

Furnace

HNO3 + AgNO3
Figure 4. Carius method for the estimation of halogens

The Carius tube is a long narrow tube closed at one end and (during the experiment) sealed at the
other end. A weighed quantity of the organic substance is taken in the tube with fuming nitric acid
and silver nitrate, then the open end is sealed and the tube is heated in a furnace. The organic
compound decomposes and silver halide is formed. At the end of the experiment, the tube is
cooled, the sealed end broken and the contents are transferred to a filter. The precipitated silver
halide is filtered, washed, dried and weighed.
Weight of AgX
Moles of AgX = = Moles of halogen in AgX
Molar mass of AgX
= Moles of halogen in organic compound
Weight of AgX  atomic mass of ha log en
Mass of halogen in organic compound =
Molar mass of AgX

Atomic mass of halogen  wt. of AgX

 Percentage of ha log en   100
(108  atomic mass of halogen)  wt. of organic compound

99.3.4 ESTIMATION OF SULPHUR

Sulphur is estimated by Carius method. The organic compound containing sulphur is heated with
fuming nitric acid. The sulphur in the compound is oxidised to sulphuric acid, which is then precipitated
as barium sulphate by adding excess of barium chloride solution. The precipitate is filtered, washed and
dried. From the weight of barium sulphate formed, the percentage of sulphur in the organic compound
can be estimated.
Weight of BaSO 4
Moles of BaSO4 = = Moles of S in BaSO4
Molar mass of BaSO 4
= Moles of S in organic compound.

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Weight of BaSO 4
Mass of sulphur in organic compound =  32
Molar mass of BaSO 4

32  weight of BaSO 4
 Percentage of sulphur   100
Molar mass of BaSO 4  weight of organic compound

32  weight of BaSO 4
  100
233  weight of organic compound

9.3.5 ESTIMATION OF PHOSPHORUS

A known mass of the organic compound is heated with fuming nitric acid, when the phosphorus
present in the organic compound is oxidised to phosphoric acid. The phosphoric acid obtained is treated
with magnesia mixture (a mixture of MgCl2, NH4CI and NH4OH) to give a precipitate of Mg(NH4)PO4,
which on ignition gives Mg2P2O7.

Weight of Mg 2P2 O 7
Moles of Mg2P2O7 =
Molar mass of Mg 2P2 O 7

2  weight of Mg 2P2 O 7
Moles P in Mg2P2O7 = = Moles of P in organic compound
Molar mass of Mg 2P2 O 7
2  weight of Mg 2P2 O 7
 Mass of phosphorous in organic compound =  31
Molar mass of Mg 2P2 O 7
2  31 weight of Mg 2 P2 O 7
Percentage of phosphorus   100
Molar mass of Mg 2 P2 O 7  weight of organic compound
62  weight of Mg 2 P2 O 7
  100
222  weight of organic compound

9.3.6 ESTIMATION OF OXYGEN

There is no direct method for the estimation of oxygen in a given organic compound. It is estimated by
subtracting the sum of the percentages of all other elements in the compound from 100.
Percentage of oxygen = 100  (% of all other elements)

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STRUCTURAL IDENTIFICATION
Introduction :
The main objective of an organic chemist is the determination of the structure of a new organic
compound which has been obtained in pure state either from a natural source or synthesised in the
laboratory.

In order to establish the correct structure of an organic compound, it is necessary to detect skeleton
of compound, elements and functional groups present in the organic compound.

1. Degree of Unsaturation (DU) :

The presence of double bonds or rings within a molecule is indicated by a quantity called degree
of unsaturation.

Applications : To indentify the no. of  bonds or rings and also helpful in determining the structure
of the molecule.

Definition : Deficiency of 2H atoms with respect to fully saturated acyclic hydrocarbon is equivalent
to One DU. It is also known as Hydrogen Deficiency Index (HDI) or Double Bond Equivalence
(DBE)

–2H –2H
H3 C – H2C – CH3     CH3 – C  CH or CH2 = C = CH2 or
(DU  O)

Where n = number of carbon atoms in the molecule

Note : Total no. of cyclic rings + double bonds will gives us degree of unsaturation.
One double bond = one DU
One ring = one DU
One triple bond = two DU

(2  2  2) – 4
Ex. (i) CH2 = CH2 DU = 2
= 2/2 = 1 (ii)     DU = 2

(iii) DU = 4 (iv)       DU = 7

( 2n  2) – 6 14  – 6 14 – (5  1)
(v) C6H6O DU = 2
= 2
= 4 (vi) C6H5Cl D.U. = 2
= 4

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2. Monohalogenation :
When an alkane or a cycloalkane is treated with halogen (Cl2, Br2, F2, I2), a photochemical
reaction takes place, in which a C–H bond cleaves and a C–X bond is formed. In such reactions
if one H-atom is substituted by one halogen atom, then this is known as monohalogenation
reaction.
Applications : If a molecule has more than one type of H-atoms, then on monochlorination, it
forms a mixture of monochloroisomers. All these products (structures) are position isomers.
Conclusion : Hence, it can be concluded that the total no. of position isomers (structural) of
monochloro compounds is equal to the number of different types of H-atoms present in the
reactant. The different type of H-atoms are also known as non-identical Hydrogens or non-
equivalent Hydrogens or chemically different Hydrogens.
Note : In aromatic hydrocarbons, the hydrogen atoms of the side-chain are chlorinated, but H-atoms of
Benzene ring are stable.

Ex. (i) CH4 CH3Cl + HCl ¼1–Monochloroproduct½

Monochlorination

Cl
–
(ii) + HCl ¼1–Monochloroproduct½
Monochlorination

CH3 CH2Cl
–

(iii) ¼1–Monochloroproduct½
Monochlorination

Note : Only one monochloro product is formed because aromatic H atoms are inert towards this reaction.

(iv) CH3 – CH2 – CH2 – CH3 2 Products (structure isomers)

Monochlorination
(v) CH3–CH2–CH2–CH2–CH3 3 Products (structure isomers)
Monochlorination

(vi) 4 Products (structure isomers)

Monochlorination
CH3
–

(vii) 5 Products (structure isomers)

Monochlorination

3. Catalytic Hydrogenation :

Alkenes, Alkynes, polyenes or polyynes can be hydrogenated by using catalysts Ni/Pt/Pd at room
temperature.
All Carbon–Carbon  bonds(C=C, CC) get hydrogenate. The reaction can’t be stopped at
any intermediate stage.

Note : (i) Aromatic  bonds are stable at room temperature but can be hydrogenate at high temperature.

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(ii) It can be concluded that the hydrogenation product of an alkene or alkyne or any unsaturated
compound is always a saturated compound.

(iii) The no. of moles of H2 consumed by 1 mole of compound is equal to the no. of  bonds.

(iv) During catalytic hydrogenation carbon skelton does not change.

Application : This reaction gives an information about molecule that the molecule is saturated or
unsaturated.
General reaction :
Ni
(a) R – CH = CH – R + H2 
 R – CH2 – CH2 – R
Ni / Pt / Pd
(b) R – C  C – R + 2H2    
 R – CH2 – CH2 – R
H2

R – CH  CH – R H
2
 R – CH2 – CH2 – R
(Not isolated)
2 2H / Ni
(c) CH2 = CH – CH = CH2   
 CH3 – CH2 – CH2 – CH3

CH = CH2 CH2 – CH3

H2 / Ni
–

(d)      
room temperature
CH2 – CH3
–

H 2/Ni
(100 – 150ºC)

4. Ozonolysis :

Ozonolysis reaction is used to determine the position of C=C, CC in a molecule. In this reaction
Alkene, Alkyne and polyalkene on ozonolysis undergo oxidative cleavage. It is of two types.

(i) Reductive ozonolysis

Reagents are : (1) O3 (ozone) (2) Zn or (CH3)2S and H2O or CH3COOH
The products are carbonyl compounds (aldehydes or ketones).

(ii) Oxidative ozonolysis

Reagents are : (1) O3 (ozone) (2) H2O2 or H2O
The products are ketones and/or acids.

Note : (i) Ozonolysis does not interfere with other functional groups.
(ii) At higher temperature, the aromatic double bonds can also undergo ozonolysis reaction.

General Reaction :
(i) Reductive ozonolysis

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(1) O3
R–CH C–R R–CH=O + O=C–R + ZnO + H2O
(2) Zn/H2O
R R
(1) O3
R–CC–H R–C–C–H + ZnO + H2O
(2) Zn/H2O
OO

(ii) Oxidative ozonolysis

(1) O3
R–CH C–R (2) H O R–COOH + O=C–R + H2O
2 2

R R
(1) O3
R–CC–H (2) H2O2 R–COOH + HCOOH

(1) O3
Ex. (a) CH2=CH2 CH2=O + CH2=O
(2) Zn/H2O
(1) O3
(b) CH3–CH2–CH=CH2 CH3–CH2–CH=O + O=CH2
(2) Zn/H2O
(1) O3
(c) CH2=CH–CH2–CH=CH–CH3 CH2=O + O=CH–CH2–CH=O + O=CH–CH3
(2) Zn/H2O

(1) O3
(d) 2 OHC–CH2–CHO (Propandial)
(2) Zn/H2O

(1) O3
(e) O=CH–CH2– C –CH2–CH=O + O=CH2
(2) Zn/H2O
O

O ( )
3
(f) Zn,H O or (glyoxal)
2

(i)O3
CH = CH – CH3 + CH3CH=O
– (ii)Zn, H2O
(g)
2 O=CH–CH=O + O=CH–C–CH=O + CH3CH=O
(ii)Zn, H2O
O

5. Practical Organic Chemistry (POC) :

When we are looking for the information regarding the functional nature of the compound then we go
for the following lab test.
(A) Test for acidic/active hydrogen :
When any compound release H2 gas after reaction with sodium or potassium or alkali metals or
sodamide then this reflect the presence of acidic hydrogen.

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Active H : Those H atoms which is attached with more electronegative atoms like O,N,S,X,
Csp .

– + 1
General reaction : Z – H + Na  Z Na + 2 H2 

Na 1 Na 1
Ex. (a) R  NH2 
 R  NHNa  H2  (b) R  SH 
 RSNa  H2 
2 2
Na 1 Na 1
(c) R  COOH 
 R  COONa  H2  (d) PhOH 
 PhONa  H2 
2 2
1
(e) R—OH + Na  R— O–Na+ + H  (f) R—SO3H + Na  R—SO3–Na + +
2 2
1
H 
2 2
1
(g) R—C  CH + Na  R—C  C–Na+ + H  (h) R —CH = CH2 + Na  No reaction.
2 2
Na 1
(i) R —CH2—O —CH3 + Na  No reaction. (j) HCl 
 NaCl  H2 
2

(B) Test for unsaturation :

(i) Bromine water test ( Br2 + H2O, Red-brown solution) :

This is used to distinguish between saturated (alkane) and unsaturated (alkene/alkyne) hydrocabon.

Br2 ,H2O
R–CH2 –CH3    no reaction
Br ,H O
R–CH = CH2 22  Red-brown colour disappear

Br2 ,H2O
R–C CR    Red-brown colour disappear

(ii) Baeyer Reagent (Cold dil. alkaline KMnO4 Pink/purple solution) :

This is also used to distinguish between saturated (alkane) and unsaturated (alkene/alkyne)
hydrocabon.

Cold, dil.KMnO4
R–CH2 –CH3     no reaction

Cold, dil.KMnO4
R–CH = CH2     Purple colour disappear

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Cold, dil.KMnO4
R–C CR     Purple colour disappear

(C) Test for terminal Alkyne


(i) Tollen’s Reagent [AgNO3 + NH4OH or {Ag(NH3)2}+ OH ] :

Tollen’s Reagent gives white precipitate (Silver alkynide) with terminal alkyne.
AgNO3 NH4OH
R–C  CH      R–C  CAg + NH4NO3

White precipitate

(ii) Ammonical cuprous chloride (Cu2Cl2 + NH4OH) :

It gives Red precipitate with terminal alkyne.

Cu 2Cl 2 NH 4OH
2 R–C  CH    2 R–C  CCu  + 2NH4Cl + 2H2O
Red precipitate

(D) Test for alcohols :

(i) Lucas Reagent test (Conc. HCl + anhydrous ZnCl2)

* It gives white turbidity or cloudiness with alcohols (OH groups attached with sp3 carbon).
* Lucas Reagent used to distinguish between 1°, 2°, 3° alcohol because 1°, 2°, 3° alcohols react with
different rate.

(a) 1° alcohol R–CH2–OH

(does not give appreciable reaction or gives turbidity in 30
min.)
(b) 2° alcohol R2CH –OH (gives white turbidity in 5 min.½

(c) 3° alcohol R3C – OH R3C–Cl (gives white turbidity immediately)

* Phenols and enols do not give Lucas test.

(ii) Victor Mayer test :

1° Alcohol%

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NO2
P+I2 AgNO2 HNO2 base
R–CH2–OH R–CH2 R–CH2–NO2 R–C= N–OH Blood Red colour

2° Alcohol%

3° Alcohol %

(iii) Cerric Ammonium Nitrate test :

Alcohols(1°, 2°, 3°) also give characteristic red colour with cerric ammonium nitrate solution.

(E) Test for phenol or enol :

Neutral FeCl3 test :
It form coloured complex with phenol or enol (OH groups attached with sp2 carbon).
3
  
6 PhOH + FeCl3   PhO  Fe  3HCl + 3H+
 6 
(Coloured complex)

* It does not give test with alcohol.

(F) Test for carbonyl compounds :

2, 4-DNP ¼2, 4– Dinitrophenyl hydrazine+½Test :

Carbonyl compouds (all aldehydes and ketones) give yellow–orange precipitate with 2,4–DNP. It is
also knwon as Brady’s reagent.
C=O + H2N – NH NO2 C=N – NH NO2
NO2 NO2
2, 4-DNP (yellow–orange precipitate of Hydrazone)

(G) Test for Aldehydes :


(i) Tollen’s Reagent [AgNO3 + NH4OH or {Ag(NH3)2}+ OH ] :

Tollen’s Reagent gives silver mirror or Black precipitate with aldehydes.

O
AgNO3 NH4OH ||
R–CH = O      R – C – O
+ Ag 
silver mirror
(ii) Fehling or Benedict test (Cu2+ in basic medium) %

Aliphatic aldehyde gives red precipitate of Cu2O with Fehling/Benedict solution. Cu2+ reduced into
Cu1+and aldehyde oxidised into acid salt.

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* Aromatic aldehydes do not give this test.

(H) Iodoform Test :

Reagents : I2 + NaOH or NaOI ¼Where R = H, alkyl, aryl group½

Acetaldehyde, all methyl ketones, ethyl alcohol and all methyl alcohols give Iodoform test.

(I) Test for acids/esters/amides :

(i) Sodium bicarbonate test (NaHCO3) %

All the acids which are stronger than H2CO3 give CO2 gas with NaHCO3.

HCl + NaHCO3  NaCl + H2CO3

 H2O + CO2 

RSO3H + NaHCO3  RSO3Na + H2CO3

 H2O + CO2 

Note : If electron withdrawing group (NO2) is present at ortho and para position of phenol then it gives
positive test with sodium bicarbonate.

(ii) Litmus test % Acid converts blue litmus into red litmus while base converts red litmus into blue.

(iii) Acid amide gives smell of ammonia when heated with alkali.

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(iv) Esters are sweet (fruity) smelling liquids.

When react with NaOH & Phenophthalein then pink colour will disappear on heating.

RCOOR’ + NaOH + Phenophthalein (Pink)  R COOH + R’ OH (Colourless solution)

(J) Test for Amines :

(i) NaNO2 + aqueous HCl test % it is used to distinguish between 1º, 2º and 3º amines and also
distinguish between aliphatic and aromatic primary amines.

1° Aliphatic Amine % R–CH2–NH2 R–CH2–OH + N2 

1° Aromatic Amine : ¼diazonium salt)

2° Amine % R – NH – R (N -Nitroso amine) yellow oily liquid

3° Amine : R3N unstable nitrite

(ii) Carbyl amine test (CHCl3 + KOH)

CHCl3 KOH
1° Amine % R–CH2–NH2     R–CH2–N  C + 3KCl + 3H2O
(unpleasent smell of isocyanide)

CHCl3 KOH
Ph – NH2     Ph – N  C

* 2° Amine and 3° Amine do not give this test.

(iii) Hofmann mustard oil test

It is a test for 1º amine and aniline. Primary amine reacts with carbon disulphide to form dithioalkyl
carbamic acids which decompose on heating with mercuric chloride (HgCl 2) to give alkyl
isothiocyanates having smell like mustard oil .
SH HgCl2
|

(a) R – NH2 + S=C=S  R – NH – C  

 R – N = C = S + HgS + 2HCl

||

S
Dithioethylcarbamic acid Alkylisothiocyanate

 HgCl2
(b) CH3CH2NH2 + S=C=S       CH3CH2–N = C=S + HgS + 2HCl

(1º amine) Ethyl isothiocyanate

Similarly aniline gives phenlyisothiocyanate

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(i) S=C=S
(c) C6H5NH2 C6H5N=C=S
(ii) HgCl2/
Phenylisothiocyanate

* 2° Amine and 3° Amine do not give this test.

(iv) Hinsberg reagent (C6H5SO2Cl) :

This is used to distinguish between 1°,2° & 3° amine.

Pyridine Base
1° Amine % R–NH2 + PhSO2Cl R–NH–SO2–Ph Compund is soluble in
base.

Pyridine Base
2° Amine % R2NH + PhSO2Cl R2N–SO2–Ph Compund is insoluble in
base.

Pyridine
3° Amine : R3N PhSO2Cl No reaction.

(K) Test of Nitro group : (Mulliken- Barker’s Test)

Nitroalkane & nitrobenzene gives black ppt on reduction with Zn and ammonium chloride followed
by treating with Tollen’s reagent. This is also said to be Mulliken’s test.

(a) R–NO2 R–NHOH Ag

Ag

(b) + Zn + NH4Cl  AgNO NH OH

3 
4  
  

(L) Test for Carbohydrates & Sugars

Molisch test :
This is a general test for carbohydrates. One or two drops of alcoholic solution of -naphthol is
added to 2 ml glucose solution. 1 ml of conc. H2SO4 solution is added carefully along the sides
of the test tube. The formation of a violet ring at the junction of two liquids confirms the
presence of a carbohydrate or sugar.

(M) Test for Amino acids and Proteins :

Ninhydrin Test :
This is used to detect the presence of amino acids & proteins.

6. Elements detection :
(A) Detection of Carbon and Hydrogen :
Carbon and hydrogen are detected by heating the compound with copper(II) oxide. Carbon present
in the compound is oxidised to carbon dioxide (tested with lime-water, which develops turbidity)

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and hydrogen to water (tested with anhydrous copper sulphate, which turns blue).
C + 2CuO 
 2Cu + CO2
2H + CuO 
 Cu + H2O
CO2 + Ca(OH)2 
 CaCO3 + H2O
5H2O + CuSO4 
 CuSO4.5H2O
White Blue

(B) Detection of Other Elements :

Nitrogen, sulphur, halogens and phosphorus present in an organic compound are detected by
“Lassaigne’s test”. The elements present in the compound are converted from their covalent form
to their ionic form by fusing the organic compound with sodium metal.
Following reactions take place: C, N, S and X come from organic compound.
Cyanide, sulphide and halide of sodium so formed on sodium fusion are extracted from the fused
mass by boiling it with distilled water. This extract is known as sodium fusion extract or Lassaigne
solution.

Na + C + N  NaCN

2Na + S  Na2S

Na + X  NaX

Na + C + N + S  NaSCN

(i) Test for Nitrogen :

The sodium fusion extract is boiled with iron(II) sulphate and then acidified with dilute sulphuric
acid. The formation of Prussian blue or green colour confirms the presence of nitrogen. Alternatively
FeCl3 and dil. HCl may be added.
6NaCN + FeSO4  Na4[Fe(CN)6]
Na4[Fe(CN)6] + 4Fe3+   Fe4[Fe(CN)6]3. xH2O
xH 2O

Ferric ferrocyanide (Prussian blue)

(ii) Test for Sulphur
(a) The sodium fusion extract is acidified with acetic acid and lead acetate is added to it. A black
precipitate of lead sulphide indicates the presence of sulphur.
Na2S + (CH3COO)2Pb  PbS
Black

(b) On treating sodium fusion extract with sodium nitroprusside, appearance of a violet colour
indicates the presence of sulphur.
Na2S + Na2[Fe(CN)5 NO]  Na4[Fe(CN)5NOS]
Sodium thionitroprusside (Violet/Purple)

(c) In case, nitrogen and sulphur both are present in an organic compound, then sodium thiocyanate
is formed. It gives blood red colour with neutral FeCl3.
Na + C + N + S  NaSCN

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FeCl3 + NaSCN  Fe(SCN)3

Blood red

(iii) Test for Halogens :

The sodium fusion extract is acidified with nitric acid and then treated with silver nitrate. A white
precipitate, soluble in ammonium hydroxide shows the presence of chlorine, a yellowish precipitate,
sparingly soluble in ammonium hydroxide shows the presence of bromine and a yellow precipitate,
insoluble in ammonium hydroxide shows the presence of iodine.
Note : The sodium fusion extract is first boiled with concentrated nitric acid to decompose
cyanide or sulphide of sodium formed during Lassaigne’s test. These ions would otherwise
interfere with silver nitrate test for halogens.
NaX + AgNO3  AgX 

(iv) Test for Phosphorus :

The compound is heated with an oxidising agent (sodium peroxide). The phosphorus present in
the compound is oxidised to phosphate. The solution is boiled with nitric acid and then treated with
ammonium molybdate. A yellow colouration or precipitate indicates the presence of phosphorus.
Na3PO4 + 3HNO3  H3PO4 + 3NaNO3
H3PO4 + 12(NH4)2MoO4 + 21 HNO3  (NH4)3PO4. 12 MoO3 + 21 NH4NO3 + 12H2O
Ammonium Ammonium
molybdate Phosphomolybdate

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Solved Examples (Objective)

Example 1:
Diabetes is detected by testing urine of the patient with
(A) Brady’s reagent (B) Nessler’s reagent
(C) Fenton’s reagent (D) Benedict’s solution
Solution:
Diabetes is due to disfunctioning of pancreas, which stops releasing insulin. Due to this sugar is
not metabolized and thus, it is passed in the urine. Benedict’s test can detect the presence of
sugar in the urine.
 (D)
Example 2:
The commonest disaccharide has the molecular formula
(A) C10H18O9 (B) C10H20O10
(C) C11H22O11 (D) C12H22O11
Solution:
The most common disaccharide is sucrose, whose molecular formula is C12H22O11.
 (D)
Example 3:
Consider following reagents,
(I) Br2 water (II) Tollen’s reagent and (III) Fehling’s solution.
Which reagent(s) can be used to make distinction between an aldose and a ketose?
(A) (I), (II) and (III) (B) (II) and (III)
(C) (I) only (D) (II) only
Solution:
Br2 water oxidises aldose to corresponding acid and it get decolourised. Ketoses are not oxidised
by Br2 water.
 (C)

Example 4:
O

This structure of glycine (amino acid) is H3NCH2CO (zwitter ion).

Select the correct statement of the following.

(A) Glycine, as well as other amino acids are amphoteric .

(B) The acidic functional group in amino acids is NH3 .
(C) The basic functional group in amino acids is CO2 .
(D) All the statements are correct.

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Solution:
Glycine and all other amino acids are amphoteric because of the presence of NH2 and CO2H

group both. The amino acid exists and zwitterion and acidic group is NH3 while basic group is
CO2 .

 (D)
Example 5:
The dipeptide, Gly.Ala has structure
O O
 
(A) H3NCH2CNHCHCO2 (B) H3NCH2CNHCHCO2
CH3 CH3
O O

(C) O2CCHNHCCH2NH3 (D) O2CCH2NHCCHNH3
CH3 CH3
Solution:
By convention, the amino acid with the free amino group (Nterminus) is written at the left end
and the one with the unreacted carboxyl group (Cterminus) at the right end. Thus, the structure
O

of Gly.Ala is H3NCH2CNHCHCO2 .
CH3
 (A)

Example 6:

The two forms of Dglucopyranose are

(A) epimers (B) anomers
(C) enantiomers (D) geometrical isomers
Solution:

The D(+)glucopyranose and D(+) CH2OH CH2OH

glucopyranose differ in their configuration at first O O
H H H OH
chiral carbon atom. Such diastereomers are called H H
anomers. OH H
HO
OH H
HO OH H
 (B) H OH H OH
D(+)glucopyranose D(+)glucopyranose

Example 7:
+ +
NH3 (y) NH3
(z)
Acidic order of is
COOH
(x)

(A) (z) > (y) > (x) (B) (y) > (x) > (z) (C) (x) > (y) > (z) (D) (x) > (z) > (y)
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Solution:
Since, carboxylic acids are more acidic than ammonium ions, most acidic would be x. CO2H group
exerts a greater I on aminium group than on  aminium group. Thus, y is more acidic than z.
 (C)

Example 8:
Which pair of compounds gives Tollen’s test?
(A) Glucose & Fructose (B) Sucrose & Glucose
(C) Hexanal & Acetophenone (D) Fructose & Sucrose

Solution:
Glucose being an aldehyde gives Tollen’s test while fructose, which is an hydroxy ketone,
tautomerizes to glucose in basic medium. Hence, it would also give Tollen’s test.
 (A)

Solved Examples (Subjective)

Example 1: Treatment of (+)– glucose with HIO4 gives results that confirm its aldohexose
structure. What product should be formed, and how much HIO4 should be
consumed.

Solution: Since in glucose there are five –OH groups so five moles of HIO4 are consumed
giving main product formic acid and formaldehyde as shown below

Glucose + 5HIO4  5HCOOH + HCHO

Example 2: Although both polymers are prepared by free radical processes, poly (vinyl
chloride) is amorphous and poly (vinylidene chloride) (saran) is highly crystallilne.
How do you account for the different? (vinylidene chloride is 1,1-dichloroethene).

H H H H H Cl H Cl
| | | | | | | |
Solution: ~~ C  C  C  C ~~ ~~ C  C  C  C ~~
| | | | | | | |
H Cl H Cl H Cl H Cl
Poly ( vinyl chloride ) PVC Poly ( vinylidene chloride) saran

As poly (vinyl chloride) is able to show stereoisomerism and further it is formed by

a free radical process, it is atactic (chlorine atoms distributed randomly), the
molecules fit together poorly.

Poly (vinylidene chlroide) has two identical substituents on each carbon and the
chains fit together well.

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Example 3: a) What is the structure of nylon-6, made by alkaline polymerisation of

caprolactom?
O
C
N
H
Caprolactam
b) Suggest a mechanism for the process. Is polymerisation of the chain
reaction or step reaction type?

H H
| |
Solution : a) ~~ N(CH2 )5 C  N(CH2 )5 C ~~
|| ||
O O

b)
–
Base – C (CH2)5 – NH
Base: C–N O
O H

Base – C (CH2)5 – NH
– H
–
O Base – C (CH2)5 – N – C(CH2)5 – NH , etc
C–N O O
O H

The reaction is anionic chain reaction polymerization, involving nucleophilic

substitution at the acyl group of the cyclic amide. The base could be OH– itself or
the anion formed by abstraction of the –NH proton from a molecule of

Example 4:
Compound (A) C5H10O5, give a tetraacetate with Ac2O and oxidation of (A) with Br2H2O
gives an acid, C5H10O6. Reduction of (A) with HI and red phosphorous gives
2methylbutane. What is structure of (A)?
Solution:
The formation of tetraacetate indicates presence of 4 OH groups and oxidation with bromine
water indicates presence of CHO group. Reduction with red phosphorous and HI indicates
presence of one carbon in the side chain. Thus, the structure of (A) would be
CHO

CHOH

HOCH2COH
CH2OH

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Example 5:
Compound (A) C5H10O4, is oxidised by Br2H2O to the acid, C5H10O5. (A) forms a triacetate
(Ac2O) and is reduced by HI to npentane. Oxidation of (A) with HIO4 gives, among other
products, 1 molecule of CH2O and 1 molecule of HCO2H. What are the possible structures
of (A) and how could you distinguish between them?
Solution:
(A) is an aldehyde, contains three hydroxyl groups and the carbon skeleton consists of five
carbon atoms in a straight chain. Also, the formula C5H10O4 therefore suggests that (A) is a
deoxysugar.
If we now try to work out the possibilities based directly on the periodic oxidation of (A), we shall
find it difficult to get an answer. In a case like this, it is simpler to use what we have deduced so
far and then see what can be deduced from the periodic acid oxidation. This approach is
reasonable provided that the number of the possibilities is relatively small. Hence, we have (by
systematically shifting the CH2 group down the chain).
CHO CHO CHO CHO
CH2 CHOH CHOH CHOH
CHOH CH2 CHOH
CHOH
CHOH CHOH
CH2 CHOH
CH2OH CH2OH CH2OH CH3
(I) (II) (III) (IV)

Now, the periodic acid oxidation produces one molecule of CH2O and one molecule of HCO2H.
Inspection of the structures shows that (I) and (II), but not (III) and (IV), can give the required
products. Hence, (A) is ether (I) or (II).
(I) and (II) may readily be distinguished by reaction with phenylhydrazine. (I) forms a
phenylhydrazone, but (II) forms an osazone.

Example 6:
Treatment of (R)–MeCH(OH)CCl3, first with alkaline NaN3 and then reducing the product

with H2/Pd yields (S)–alanine, CH3CH (N H 3 ) CO 2– . Explain.
Solution:
In alkaline solution, the OH will be converted to O– which displaces Cl of adjacent carbon to form
an oxirane ring. In the oxirane ring, the configuration of chiral carbon is still (R). The oxirane ring
is then opened by nucleophilic attack of azide ion, which occurs with inversion of configuration
i.e. configuration becomes (S). The acid chloride will be hydrolysed in alkaline conditions to give
acid. This is followed by reduction of N3 group to give (S)– alanine.
OH O–
Me O Cl
OH–  Cl –
Me – C – CCl3  Me – C – CCl2 
 C – C
(R) Cl Cl
–
N3

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Me Me Me O–
– –
N3 – C – C – O OH  Cl –
 N3 – C – C – Cl   N3 – C – C – Cl
O O Cl
H2/Pd, – N2
Me

–
H3 N – C – CO2
(S) – alanine

Example 7:
The pKa of the carboxyl group in an amino acid valine, (CH3)2CHCH(NH2)(COOH) is 2.31
and the pKa for the amino group of the same amino acid is 9.69. Compute the isoelectric
point (pI) for valine and draw the structure of this amino acid when the pH of the solution
equals to pI. Also draw the structures of valine that predominate at pH = 2 and pOH = 2.
Solution:
The isoelectric point (pI) is the pH at which the amino acid exists only as a dipolar ion with net
charge zero.
(pK a1  pK a 2 )
At isoelectric point, for a neutral amino acid, pI =
2
The dissociation of cationic form of valine can be represented as
CO2H CO 2 CO 2
 
CH N H 3 (pKa1) CH N H 3 (pKa2) CHNH2
OH– OH–
CH(CH3)2 CH(CH3)2 CH(CH3)2
H+ H+

Net charge (+1) (0) (1)

The species with zero net charge exists between species with (+1) and (–1) net charges.

(pK a1  pK a 2 ) 9.69  2.31

pI = = =6
2 2

CO 2

When the pH of the solution equals to pI, the structure of valine is CH N H 3 .
CH(CH3)2

CO2H


When the pH of the solution is two, the structure of valine is CH N H 3 .

CH(CH3)2

CO 2
When the pH of the solution is 12, the structure of valine is CHNH2.
CH(CH3)2

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Example 8:

A mixture of pamino benzoic acid and phydroxy benzoic acid is taken in diethyl ether.
How will you separate them (in not more than three steps)? Write the reagents and all the
required conditions to separate them. Give confirmatory test for the presence of each
functional group.
Solution:

pamino benzoic acid, phydroxy benzoic acid

(in ether)

Step 1. Extract with aq. dil. HCl

Ether layer Aqueous layer

+
pHOC6H4CO2H pCO2HC6H4NH3 Cl

Separate the two layers using separating funnel.

Step 2. Basification of aqueous layer with NaOH.
Test for NH2 group: When compound containing NH2 group is heated with CHCl3 and KOH, a
very pungent smell of isocyanide is obtained.
RNH2 + CHCl3 + 3KOH  RNC + 3KCl + 3H2O.
Test for COOH group: The compound containing COOH group gives brisk effervescence on
treatment with NaHCO3 solution due to evolution of CO2.
Test for OH group: A blue or green colouration is obtained when the compound is treated with
neutral FeCl3 solution.
Example 9:
0.21 g of an organic compound gave on combustion 0.462 g of carbon dioxide and 0.1213
g of water. Calculate the percentage of carbon and hydrogen in it.
Solution:
0.462  12
% of carbon in the organic compound =  100 = 60%
44  0.21
0.1213  2
and % of hydrogen in the organic compound =  100 = 6.41%
18  0.21

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EXERCISE-1 (EXERCISE FOR JEE MAIN)

1. Which of the following is the structure of Dxylose?

CHO CHO
HO H HO H
(A) H OH (B) HO H
H OH H OH
CH2OH CH2OH
CHO CHO
H OH H OH
(C) HO H (D) H OH
H OH H OH
CH2OH CH2OH

2. Identify the product ‘Z’ in the following series of reactions


HCN H O HI
C6H12O6(glucose)  X 3  Y  Z
(A) Hexanoic acid (B) methyl caproic acid
(C) Heptanoic acid (D) None of these

3. Invert sugar is
(A) Chemically inactive form of sugar.
(B) Equimolecular mixture of glucose and fructose.
(C) Mixture of glucose and sucrose.
(D) A variety of cane sugar.

4. When sucrose is heated with concentrated nitric acid the product is

(A) Saccharic acid (B) Oxalic acid
(C) Formic acid (D) Invert sugar

5. The carbohydrate which serves as reserve glucose in body is

(A) Sucrose (B) Starch
(C) Glycogen (D) Fructose

6. Acetyl derivative of which carbohydrate is used in sizing of paper industry?

(A) Glucose (B) Fructose (C) Lactose (D) Starch

7. Sugars are characterised by the preparation of osazone derivatives. Which of the following
sugars have identical osazones?
(A) Glucose and lactose (B) Glucose and fructose
(C) Glucose and arabinose (D) Glucose an maltose
8. Glucose when heated with CH3OH in presence of dry HCl gas,  and methyl glycosides
are formed. This is because it contains
(A) an aldehydic group (B) CH2OH group
(C) a ring structure (D) five hydroxyl groups

9. Ribose sugar is a component of

(A) DNA (B) RNA
(C) Glucose (D) Wax
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10. Glycogen is
(A) a polysaccharide found in both animals and plants.
(B) a polysaccharide found in plants.
(C) a polysaccharide found in animals.
(D) a polysaccharide found in honey.

11. Dihydroxy acetone (CH2OH.CO.CH2OH) has the general formula of carbohydrate but not
included in this class because
(A) It does not contain polyhydroxy group.
(B) It does not contain aldehyde group.
(C) It does not contain asymmetric carbon atom.
(D) All of the above.

12. The polymer formed with more than two monosaccharide units is known as
(A) Disaccharide (B) Polysaccharide
(C) Both (A) and (B) (D) None of these

13. A solution of Dglucose in water rotates the plane of plane polarised light.
(A) To the right (B) To the left
(C) To either side (D) None of these

14. The number of atoms in the ring structure of pyranoses are

Carbon Oxygen
(A) 5 1
(B) 4 2
(C) 4 1
(D) 3 2

15. Which statement about ribose is incorrect?

(A) A polyhydroxy compound. (B) An aldehyde sugar.
(C) Has six carbon atoms. (D) Exhibits optical activity.

16. In fermentation by zymase, alcohol and CO2 are obtained from

(A) Glucose (B) Invert sugar
(C) Fructose (D) All of these
17. Which is used to identify glucose?
(A) Neutral ferric chloride (B) CHCl3 + KOH (alc.)
(C) Ammonical AgNO3 (D) C2H5ONa
18. Ring structure of glucose is due to formation of hemiacetal and ring formation between
(A) C1 and C5 (B) C1 and C4
(C) C1 and C3 (D) C3 and C4
19. In lactose, the reducing part is
(A) Galactose (B) Glucose
(C) Fructose (D) Mannose
20. Cellulose is a linear polymer of
(A) glucose (B) glucose
(C) fructose (D) none of these
58 CLASS XII CHEMISTRY
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21. An aldose is converted into its next higher homologue by
(A) Ruff’s method (B) Amadori rearrangement
(C) Killiani’s synthesis (D) None of these

22. Dglucose in dilute alkaline or acidic solution contains

(A) 50% each of Dglucose and Dglucose
(B) 64% of Dglucose and 36% of Dglucose
(C) 36% of Dglucose and 64% of Dglucose
(D) 33% of each of Dglucose, Dglucose and open structure

23. Glucose molecule reacts with ‘X’ molecule of phenyl hydrazine to yield the osazone.
The value of ‘X’ is
(A) 4 (B) 1
(C) 2 (D) 3

24. The two forms of Dglucopyranose obtained from solution of Dglucose are known as
(A) Epimers (B) Anomers
(C) Enantiomers (D) Geometrical isomers

25. Glucose and cane sugar can be distinguished by

(A) Fehling’s solution (B) Baeyer’s reagent
(C) Molisch test (D) Iodine solution

26. Glycogen and amylopectin have

(A) same structure.
(B) similar structure but differ in branching of glucose chain.
(C) similar structure but differ in their solubility in water.
(D) same structure but they are stored in different parts of the body.

27. Number of chiral carbon atoms in D(+) glucose is

(A) 5 (B) 6
(C) 3 (D) 4

28. Buna N is a polymer of

(A) 1, 3-butadiene and acrylonitrile (B) Acrylonitrile
(C) Styrene (D) None

29. Teflon, polystyrene and neoprene are all

(A) Copolymers (B) Condensation polymers
(C) Homopolymers (D) Monomers
30. Terylene (Dacron) is a condensation polymer of
(A) Formaldehyde and urea
(B) Ethylene glycol and ethylene diisocyanate
(C) Ethylene glycol and dimethyl terephthalic acid
(D) Maleic anhydride and methyelene glycol
31. Polystyrene is a
(A) Copolymer (B) Addition polymer
(C) Condensation polymer (D) None

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32. Proteins contain
(A) exclusively D isomers of amino acids
(B) exclusively L isomers of amino acids
(C) 50% of each of D and L amino acids
(D) 33% of Dform and 67% of Lform of amino acids

33. Nylon-6,6 is an example of

(A) Fibres (B) Elastomer
(C) Thermoplastic (D) Thermosetting polymer

34. Teflon is an example of:

(A) Fibres (B) Elastomer
(C) Thermoplastic (D) Thermosetting polymer

35. Nylon-6 is a polyamide having monomer

(A) Caprolactam (B) Cyclohexane
(C) Cyclohexanone-oxime (D) None.

36. Natural rubber is a polymer of

(A) Chloroprene (B) Isoprene
(C) 1, 3-Butadiene (D) None

37. The pH value of a solution in which a polar amino acids does not migrate under the
influence of electric field is called
(A) Iso electric point (B) Iso electronic point
(C) Neutralisation point (D) None

38. The sequence in which amino acids are arranged in protein is called
(A) Primary structure (B) Secondary Structure
(C) Tertiary Structure (D) Quaternary structure
39. Isoelectric point (pI) is the pH at which
(A) AA exits only as dipolar ion
(B) AA exits only as monobasic acid
(C) AA is only as diboric acid
(D) AA is only as protonated acid

40. Secondary structure of protein refers to

(A) three dimensional structure, especially the bond between amino acid residues that
are distant from each other in the polypeptide chain.
(B) regular folding patterns of the polypeptide chain.
(C) mainly denatured proteins and structures of prosthetic groups.
(D) linear sequence of amino acid residues in the polypeptide chain.

41. At the isoelectric point, amino acids are present as


(A) H2NCH(R)COOH (B) H3 N CH(R )COO 

(C) H3 N CH(R )COO H (D) H2NCH(R)COO

60 CLASS XII CHEMISTRY

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 
42. If K a1 and K a 2 are the ionization constants of H3 N CH(R )COOH and H3 N CH(R )COO  ,
respectively, the pH of the solution at the isoelectric point is
(A) pH = pKa1 + pKa2 (B) pH = (pKa1 pKa2)1/2
(C) pH = (pKa1 + pKa2)1/2 (D) pH = (pKa1 + pKa2)/2

43. Which of the following amino acid is not optical active?

(A) Glycine (B) Alanine
(C) Valine (D) Glutamic acid
44. Ribose sugar is a component of
(A) DNA (B) RNA
(C) Glucose (D) Wax

45. In glycine, the basic group is


(A) NH2 (B)  NH 3
(C) COOH (D) COO
46. The normal method for estimation of nitrogen is
(A) Duma’s method (B) Kjeldahl’s method
(C) Carius method (D) Liebig method

47. The simple formula of a compound is CH2. One mole of the compound weighs 42 g.
Its molecular formula is
(A) CH2 (B) C2H2
(C) C3H6 (D) C3H8
48. The compound that does not give a blue color in Lassaigne’s test is
(A) Aniline (B) Glycine
(C) Hydrazine (D) Urea

49. The Lassaigne solution gave violet colour when treated with sodium nitroprusside.
It indicates the presence of
(A) N (B) S
(C) I (D) both N and S
50. In a compound C = 40% and H = 6.66%. What is the empirical formula?
(A) CHO (B) CH2O
(C) C3HO (D) C4HO4
51. In the estimation of nitrogen by Duma’s method 1.18 g of an organic compound gave
224 ml of N2 at NTP. The percentage of nitrogen in the compound is about
(A) 20.0 (B) 11.8
(C) 47.5 (D) 23.7
52. 0.20 g of a hydrocarbon on combustion gave 0.66 g CO2. The percentage of hydrogen in the
hydrocarbon is about
(A) 33 (B) 45 (C) 10 (D) 90
53. CH3NH2 is heated with sodium and extracted with water and then AgNO3 is added. The white
ppt. obtained is of
(A) AgCN (B) Ag2SO4
(C) AgCl (D) Cl.CH2COOAg

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54. An azeotropic mixture of ethanol and water is first treated with………before subjecting for
fractional distillation to separate them.
(A) Anhydrous lime (B) C6H6
(C) Both (A) and (B) (D) None
55. In Lassaigne’s test sodium metal is used because
(A) It is very reactive. (B) Its melting point is low.
(C) Its compounds are soluble in water. (D) All of these.
56. The percentage of sulphur in the organic compound, when 0.2595 g of a sulphur containing
organic compound in a quantitative analysis by Carius method yielded 0.35 g of barium sulphate,
is
(A) 14.52% (B) 16.52%
(C) 18.52% (D) 19.52%
57. A compound containing 80% carbon and 20% hydrogen is likely to be
(A) C6H6 (B) C2H5OH
(C) C2H6 (D) CHI3
58. If 0.228 g of silver salt of dibasic acid gave a residue of 0.162 g of silver on ignition, then
molecular weight of the acid is
(A) 70 (B) 80
(C) 90 (D) 100
59. Which element does not give borax bead test?
(A) Pb (B) Cu
(C) Cr (D) Fe
60. The Lassaigne’s extract is boiled with dilute HNO3 before testing for halogens because
(A) Silver halides are soluble in HNO3
(B) Na2S and NaCN are decomposed by HNO3
(C) Ag2S is soluble in HNO3
(D) AgCN is soluble in HNO3
61. In which of the following compounds, nitrogen cannot be tested by Lassaigne’s test?
(A) C6H5NH2 (B) N2H4
(C) CH3CONH2 (D) C6H5NO2

62. To determine the weight of a halogen in organic compound, the compound is heated with fuming
HNO3 in presence of
(A) Ag (B) AgNO3
(C) Ag2CO3 (D) Ag2SO4
63. 59 g of an amide obtained from a carboxylic acid, RCOOH upon heating with alkali liberated 17
litre of ammonia at NTP. The acid is
(A) Formic acid (B) Acetic acid
(C) Propionic acid (D) None of these
64. Which of the organic compound will give red colour in Lassaigne’s test?

(A) C6H5CN (B) H2N CO2H

O
(C) NH2CNH2 (D) H2N SO3Na

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HNO 3 / AgNO 3
65. Organic compound (A)     white ppt. The organic compound (A) could be

(A) NH4Cl (B) Cl

(C) Cl (D) CH2Cl

66. Detection of the chlorine is possible without preparing sodium extract in

CH3
(A) O2N Cl (B) CHCl3

CH3

(C) CH2CH2Cl (D) CH2=CHCH2Cl

67. 6 g of the organic compound on heating with NaOH gave NH3, which is neutralised by
200 ml of 1 N HCl. Percentage of nitrogen in the organic compound would be
(A) 12% (B) 60%
(C) 46.67% (D) 26.67%

68. An organic compound (A) contains 20% C, 46.66% N and 6.66% H. It gave NH3 gas on heating
with NaOH. The organic compound (A) could be
(A) CH3CONH2 (B) C6H5CONH2
(C) NH2CONH2 (D) CH3NHCONH2

69. The sulphur content of cystine is 26.7 percent. Given that cystine contains two sulphur atoms,
molecular weight of cystine is approximately
(A) 120 (B) 240
(C) 100 (D) 60

70. A colourless salt gives violet colour in bunsen flame it may be

(A) Na2CO3 (B) Na2CrO4
(C) K2CO3 (D) BaCO3
71. Fractional crystallization is carried out to separate
(A) organic solids mixed with inorganic solids.
(B) organic solids highly soluble in water.
(C) organic solids having small difference in their solubilities in suitable solvent.
(D) organic solids having great difference in their solubilities in a suitable solvent.

72. Two substances when separated out on the basis of their extent of adsorption by one material,
the phenomenon is
(A) chromatography (B) paper chromatography
(C) sublimation (D) steam distillation

73. An organic compound X contains y and z impurities. Their solubility differs slightly. They may be
separated by
(A) simple crystallization (B) fractional crystallization
(C) sublimation (D) fractional distillation

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74. Fuels from crude oil are separated from one another by
(A) fractional distillation (B) crystallization
(C) steam distillation (D) selective adsorption

75. Sodium extract of an organic substance gives a blood red colour with FeCl3. It contains the
elements
(A) N (B) S (C) N and S both (D) N or S
76. 0.099 g of an organic compound when heated with fuming nitric acid in the presence of silver
nitrate in a carius tube gave 0.287 g silver chloride. The percentage of chlorine in the compound
is about
(A) 29.6 (B) 71.7
(C) 35.4 (D) 64.2

77. A mixture of camphor and NaCl can be separated by

(A) sublimation (B) evaporation
(C) filtration (D) decantation

78. Glycerol is decomposed below its boiling point. It may be purified by

(A) steam distillation. (B) simple distillation.
(C) fractional distillation. (D) distillation under reduced pressure.

79. Sodium extract is heated with conc. HNO3 before testing for halogens because
(A) silver halides are insoluble in HNO3. (B) Na2S and NaCN are decomposed by HNO3.
(C) Ag2S is soluble in HNO3. (D) AgCN is soluble in HNO3.

80. 0.22 g of organic compound CxHyO which occupied 112 ml at NTP and on combustion gave 0.44
g CO2. The ratio of X to Y in the compound is
(A) 1 : 1 (B) 1 : 2
(C) 1 : 3 (D) 1 : 4

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81. Glycoside linkage is

(A) an acetal linkage (B) an ether linkage (C) an ester linkage (D) an amide linkage
82. Sucrose on hydrolysis yields a mixture which is
(A) optically inactive (B) dextrorotatory (C) laevorotatory (D) racemic
83. Hydrolysis of sucrose into (+) glucose and (-) fructose is known as
(A) Muta rotation (B) Inversion (C) Pyrolysis (D) None of these
84. The letter D in D-glucose signifies
(A) dextro rotatory (B) mode of synthesis
(C) its configuration (D) its diamagnetic nature
85. Cellulose on hydrolysis yields
(A) -D-Fructose (B) -D-Glucose (C) -D-Glucose (D) -D-
Fructose
86. Glucose when treated with CH3OH in presence of dry HCl gas gives - and - methylglucosides
because it contains
(A) an aldehydic group (B) a – CH2OH group (C) a ring structure (D) five – OH group
87. Which of the following can be used for detection of traces of iodine ?
(A) Glucose in aqueous solution (B) Starch in aqueous solution
(C) Cellulose in alcoholic solution (D) Cellulose in aqueous solution
88. Which of the following pairs form the same osazone ?
(A) Glucose and fructose (B) Glucose and galactose
(C) Glucose and arabinose (D) Lactose and maltose
89. The term inverted sugar refers to an equimolar mixture :
(A) D-Glucose and D-galactose (B) D-Glucose and D-fructose
(C) D-Glucose and D-mannose (D) D-Glucose and D-ribose
90. -D glucose and -D-glucose differ from each other due to the difference in one of the carbon
atoms, with respect to its
(A) Number of OH groups (B) Configuration
(C) Conformation (D) Size of hemiacetal ring
91. Find true and False from the following statements regarding carbohydrates
S1 : All monosaccharides whether aldoses or ketoses are reducing sugars.
S2 : Bromine water can be used to differentiate between aldoses and ketoses
S3 : A pair of diastereomeric aldoses which differ only in configuration at C-2 are anomers.
S4 : Osazone formation destroys the configuration at C-2 of an aldose, but does not affect the
configuration of the rest of the molecule.
(A) TTTT (B) TFTF (C) TTFT (D) FTTT

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92. D-glucose, on treating with methanol in presence of dry HCl gives methyl glucosides according to
the following reaction

and

(I) (II) (III)

Mention true (T) and False (F) from the following statements
S1 : The glucosides do not reduce fehling's solution
S2 : The glucosides do not react with hydrogen cyanide or hydroxylamine
S3 : Behaviour of glucosides as stated in S1 and S2 indicates the absence of free – CHO group.
S4 : The two forms of glucosides are enantiomers.
(A) TTFF (B) FTTT (C) TTTF (D) TFTF
93. In Ketohexose the possible optical isomers are
(A) 12 (B) 4 (C) 16 (D) 8
94. Which of the following indicates the presence of 5 –OH groups in glucose
(A) Penta-acetyl derivative of glucose (B) Cyanohydrin formation of glucose
(C) Reaction with fehling's solution (D) Reaction with Tollen's reagent
95. Observe the following laboratory tests for glucose pentacetate and mention +ve or –ve from the
code given below.

Glucose pentacetate

(A) + + + + (B) – – – – (C) + – + – (D) + + – –

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96.  -D (+) glucopyranose is
(A) acetal (B) ketal (C) hemiacetal (D) hemiketol

97. Allose

Given monosacharide is a/an

(A) Aldopentose (B) Aldohexose (C) Ketopentose (D) Aldoheptose
98. Which of the following -amino acids is not optically active ?
(A) Alanine (B) Glycine (C) Phenylalanine (D) Cysteine
99. The name of the dipeptide
H2NCHCONHCH2 COOH
|
CH3
(A) Glycylglycine (B) Glycylalanine (C) Glycine alanine (D) Alanylglycine
100. The force of attraction between the neighbouring peptide chains is
(A) Vander Waal’s force (B) Covalent bond
(C) Hydrogen bond (D) Peptide linkage
101. Which of the following is a basic amino acid?
NH2

(A) H2N – C – NH (CH2)3 – CH – COOH (B) HOH2C – CH – NH2

NH COOH

NH2 NH2

(C) CH2 – CH2 – CH – COOH (D) HOOC – CH 2 – CH – COOH

COOH
102. Which of the following is  – amino acid?
NH2
(A) NH – CH2 – CH2 – COOH (B) CH – COOH

NH2
CH 3 – CH 2 – CH – CH 2 – NH 2
(C) CH – CH2 – COOH (D)
COOH

103. Starch is polymer of

(A) -D-Glucose (B) -D-Glucose
(C) -D-Glucose and -D-Glucose (D) -D-Fructose
104. Nylon-66 is made by using
(A) Phenol (B) Benzaldehyde (C) Adipic acid (D) Succinic acid

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105. Polymer which has amide linkage is
(A) Nylon -66 (B) Terylene (C) Teflon (D) Bakelite
106. Ziegler-Natta catalyst is
(A) K[PtCl3(C2H4)] (B) (Ph3P)3RhCl (C) Al2(C2H5)6 + TiCl4 (D) Fe(C5H5)2

107. Monomer of given polymer is :

(A) 2- Methylpropene (B) Styrene (C) Propylene (D) Ethene

108. Which of the following is a nitrogen containing polymer ?
(A) Polyvinyl chloride (B) Bakelite (C) Nylon (D) Terylene
109. Buna-S is a polymer of :
(A) Butadiene only (B) Butadiene and nitryl(C) Styrene only (D) Butadiene and styrene
110. Condensation product of caprolactum is :
(A) nylon-6 (B) nylon-6, 6 (C) nylon-60 (D) nylon-6, 10
111. The sugar present in DNA is :
(A) Glucose (B) Deoxyribose (C) Ribose (D) Fructose
112. The pentose sugar in DNA and RNA has the :
(A) Open chain structure (B) Pyranose structure
(C) Furanose structure (D) None of the above
113. Which of the following is not a pyrimidine base ?
(A) Uracil (B) Guanine (C) Cytosine (D) Thymine
114. The relationship between the nucleotide triplets and the amino acids is called
(A) Translation (B) Transcription (C) Replication (D) A genetic code
115. Which of the following statements about DNA is not correct ?
(A) It has a double helix structure
(B) It undergoes replication
(C) The two strands in a DNA molecule are exactly similar
(D) It contains the 2-deoxyribose pentose sugar.
116. Which of the following statements about RNA is not correct ?
(A) It has a single strand (B) It does not undergo replication
(C) It does not contain any pyridimine base (D) It controls the synthesis of proteins
117. Oils and fats are esters of higher fatty acids with :
(A) Ethanol (B) Glycol (C) Glycerol (D) Methanol
118. The cheif constituents of cell membranes are :
(A) Simple triglycerides (B) Waxes (C) Phospholipids (D) Proteins
119. The fats present in the body act as
(A) Food storage only (B) Heat insulator only
(C) Shock absorber only (D) All the three above
120. The most concentrated source of energy in the human body is
(A) Fats (B) Sugars (C) Proteins (D) Nuclei acids

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121. Which of the following is a vitamin ?
(A) Glucose (B) Keratin (C) Maltose (D) Riboflavin
122. Vitamin B6 is known as
(A) Pyridoxine (B) Thiamine (C) Tocopherol (D) Riboflavin
123. The best source of vitamin A is :
(A) Oranges (B) Beans (C) Carrots (D) Wheat
124. Vitamin D is called :
(A) Ascorbic acid (B) Calciferol or ergocalciferol
(C) Thaimine (D) Riboflavin
125. Which of the following is found in cod-liver oil ?
(A) Vitamin C (B) Vitamin E (C) Vitamin A (D) Vitamin B1
126. Vitamin E is also called :
(A) Cyanocobalamin (B) Tocopherol (C) Lactoflavin (D) Ascorbic acid
127. The best source of vitamin C is :
(A) Code liver oil (B) Egg yolk (C) Citrus fruits (D) Fish liver oil
128. Milk contains vitamins :
(A) A, D and E (B) A, B12 and D (C) C, D and K (D) B1, B6 and D
129. Nervousness anaemia is caused by the deficiency of vitamin
(A) B1 (B) B2 (C) B6 (D) B12
130. Deficiency of vitamin E causes
(A) Scurvy (B) Loss of appetite
(C) Loss of sexual power and reproduction (D) Beriberi
131. Which of the following is fat soluble vitamin ?
(A) Vitamin A (B) Pyridoxine (C) Riboflavin (D) Thiamine
132. Which one of the following vitamin contains a metal atom ?
(A) Vitamin A (B) Vitamin B2 (C) Vitamin B6 (D) Vitamin B12
133. Identify the vitamin whose deficiency in our food decreases reproductive power :
(A) vitamin A (B) vitamin C (C) vitamin D (D) vitamin E
134. Beri-beri is casued due to :
(A) vitamin A (B) vitamin B (C) vitamin C (D)vitaminD

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135. The DU of following compound C8H12O, C3H5N, C4H8O are respectively :
(A) 4,3,2 (B) 3,2,1 (C) 2,1,3 (D) 2,2,3
136. Which of the following compounds have same degree of unsaturation.

(A) I, II (B) I and III (C) I, II and III (D) I, II and IV

137. Which of the following hydrocarbons give same product on hydrogenation.
(A) 2-Methyl hex-1-ene & 3-Methyl hex-3-ene
(B) 3-Ethyl hex-1-en-4-yne & 2-Methylhept-2-en-4-yne
(C) 3-Ethylcycloprop-1-ene & 1,2-Dimethylcycloprop-1-ene
(D) 2-Methylbut-2-ene & 3-Methylbut-1-ene
138 Only two isomeric monochloro derivatives are possible for :-
(A) n-Pentane (B) 2,4-Dimethyl pentane
(C) Toluene (D) 2,3-Dimethyl butane
139 The number of possible monochloro derivatives of 2, 2, 3, 3-Tetramethylbutane is -
(A) 2 (B) 3 (C) 4 (D) 1
140. Which of the following alkene gives four monochloro (structural isomer) products after hydrogenation?
(A) Pent-2-ene (B) 2-Methylbut-2-ene
(C) 3-Methylhex-2-ene (D) 2, 3-Dimethylbut-2-ene
141. Which of the following compound will give four monochloro (structural) product on monochlorination.

(A) (B) (C) (D)

142. Compound A (C6H12) does not absorb H2 in presence of Ni. It forms two monochloro isomers on
photochemical chlorination. Its structure can be :

(A) (B) (C) (D)

143. Identify E in the following sequence of reaction.

H / Ni
E (C6H10) 2  F (C6H12) G (C6H111Cl) (only one isomer)

(A) (B) (C) (D)

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144 An organic compound C4H6 on ozonolysis gives Formaldehyde and Glyoxal. What is the structure of
organic compound ?

(A) (B) (C) (D) CH3–CH2–CCH

O / Zn
145 X 3  +

Y..

The IUPAC name of compound Y is :

(A) 2-Cyclohexyl butane (B) 1-Methyl propyl cyclohexane
(C) Butyl cyclohexane (D) 1-Cyclohexyl butane
146. An alkene give two moles of HCHO, one mole of CO2 and one mole of on

ozonolysis. What is its structure?

(A) (B)

(C) (D)

147. An unknown compound on ozonolysis to give acid C3H6O2 and a ketone C4H8O. From this information,
identifiy structure of unknown compound.
CH3

(A) (CH3)2C = CHCH2 – CH2CH3 (B) CH3CH2 – C = CHCH2CH3

(C) (CH3)2CHCH = CHCH2CH3 (D) CH3CH2CH2CH = CHCH2CH3
148. A hydrocarbon C6H4 gives C3H2O3 on reductive ozonolysis. The hydrocarbon is :

(A) (B) (C) (D)

149 Which of the following compound on reductive ozonolysis gives 3, 4-Dioxopentanal and 3-Oxohexane-
1,6-dial.

(A) (B) (C) (D)

150 Identify the structure of compound which consume only one mole H2 gas during hydrogenation and
give only 2-monochloro structural products after hydrogenation. It yield only ketone after reductive
ozonolysis.

(A) (B) (C) (D)

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151. When one mole of the given compound reacts with sodium metal then how many moles of H2 gas
will release?
NO 2 O
||
OH
(1mole)
||
O
(A) 1 mole (B) 1.5 mole (C) 2 mole (D) 0.5 mole

152.

Compound X is
(A) H3C–CC–CH3 (B) CH2=CH–CH=CH2

(C) CH3–CH2–CCH (D)

153.

Identify X :
(A) CH3 – CH2 – C  C – CH2 – CH3 (B) CH3 – C  C – CH2 – CH2 – CH3

(C) (D)

154. Ammonical AgNO3 give white ppt after reaction with any compound than this reflect the presence of
(A) One – CHO group (B) One triple bond
(C) A terminal alkyne (D) Compound is unsaturated
155. Which one of the following will not give white precipitate with ammonical silver nitrate solution
(A) CH3 – C  C – CH3 (B) CH3  CH  C  C  CH3
|
CH3
(C) CH3 – CH2 – CH = CH2 (D) All of these
156. Which will undergo reaction with ammonical AgNO3 :

(A) (B) CH3–CH=CH–CCH

(C) CH3–CH2–CH=CH–CH2–CH3 (D) CH2=CH–CH2–CH3

157. Which of the following compound gives red ppt with Cu2 Cl2 /NH4OH ?
(A) CH3  C  C  CH3 (B) CH3  CH2 – C  CH
(C) CH3 – CH2 – CH  CH2 (D) CH3 – C  C – CH  CH2

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158. Identify the hydrocarbon having molecular formula C5H6 which gives white ppt with ammonical AgNO3?
(A) (B)
(C) (D)
159. The group reagent for the test of alcohols is :
(A) cerric ammonium nitrate (B) Schiff’s reagent
(C) Molisch’s reagent (D) bromine water

160.

Identify X :

(A) (B)

(C) (D)
161. Alcohol X having four carbon atoms. It gives lucas test in 10 min. Which cannot be the alcohol X.

(A) (B) (C) (D)

162. Which of the following compounds does not show phenolic properties :

(A) (B) (C) (D)

163. The following two compounds I and II can be distinguished by using reagent

(1) aq. NaHCO3 (2) Neutral FeCl3

(3) Blue litmus solution (4) Na metal (5) HCl/ZnCl2 anhydrous
(A) 1 or 3 (B) 2 or 5 (C) 4 or 5 (D) 3 or 4
164. Which of the following compound will give black or silver ppt. with Tollen's reagent.
(A) H  C  C – CH2  C  CH3 (B) CH3  C  C  C  CH3
|| ||
O O

(C) CH3 – C  C – CH2 – CHO (D) CH2  CH  C  CH  CH2

||
O

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165. Which of the following compound will not react with I2 /OH–.

(A) (B)

(C) (D) CH3 – CHO

166. A compound which can give iodoform test, bromine water test, FeCI3 test but not Tollen's test.

(A) (B)

(C) (D)

167. Tollen’s reagent (AgNO3 + NH4OH) can be used to distinguish between.

(A) and (B) and

(C) and (D) and

168. The compound A gives following reactions.

Its structure can be

(A) (B) OHC–(CH2)2–CH=CH–COOH

(C) (D)

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169. The compound responds to Tollen's reagent is :
(A) CH3COCH3 (B) CH3CHO (C) CH3CONH2 (D) CH3COOH
170. Which of the following compound does not give yellow ppt when react with NaOI.

(A) (B)

(C) Ph–CH 2 – C – CH 3 (D)

||
O
171. 2-Pentanone can be distinguished from 3-Pentanone by which reagent ?
(A) 2, 4- Dinitrophenyl hydrazine (B) Tollen's reagent
(C) I2 and dilute NaOH (D) Fehling solution

172.

Identify 'X'.
(A) CH3 – CH2 – COOH (B) CH2 – CH2 – CH2
| |
OH OH
(C) CH3 – CO – CH2 – OH (D) CH2 = CH – CH2 – OH
173. An oragnic compound X (C4H8O2) gives positive test with NaOH and Phenopthalein. Structure of X
will be :
(A) CH3  CH2  CH2  C  OH (B) CH3  C  C  CH3
|| || ||
O O O

(C) CH3  C  O  C2H5 (D) CH3  C  OCH3

|| ||
O O
174. Which of the following compound will give smell of NH3 with conc. NaOH.
(A) CH3  CH2  C  NH2 (B) CH3  C  CH2  NH2
|| ||
O O

(C) (D) CH3  CH2  C  OH

||
O
175. Which of the following will not give positive test with CHCl3 / KOH.
(A) CH3 – CH2 – NH – CH3 (B) CH3 – CH2 – CH2 – NH2

CH3
|
(C) (D) CH3  CH  NH2

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176. A compound is heated with zinc dust and ammonium chloride and the reaction mixture is filtered
into Tollen's reagent. Formation of silver mirror indicates the presence of following group

(A) –CHO (B) (C) –NO2 (D) –NH2

177. A positive carbylamine test is given by :
(A) N,N–dimethylaniline (B) 2, 4-dimethylaniline
(C) N-methyl-o-methylaniline (D) N-methylaniline

178. The Hinsberg's method is used for :

(A) preparation of primary amines (B) preparation of secondary amines
(C) preparation of tertiary amines (D) separation of amine mixtures
179. Which of the following amine does not react with Hinsberg's reagent ?
(A) CH3CH2NH2 (B) (CH3CH2)2NH (C) (CH3CH2)3N (D) All of these
180 Molisch reagent is used to identify following compound ?
(A) Glucose (B) Raffinose (C) D-oxyribose (D) All of these
181. In the Lassaigne’s test, one of the organic compounds gave red colour with FeCl3. Compound can
be :
(A) Na2S (B) NaCNS (C) C6H5Cl (D) NH2CSNH2
182. Lassaigne’s test is used in qualitative analysis to detect
(A) Nitrogen (B) Sulphur (C) Chlorine (D) All of these
183. The compound that does not give a blue colour in Lassaigne’s test is
(A) C6H5–NH2 (B) CH3CONH2 (C) NH2–NH2 (D) C6H5–NO2
184. Nitrogen containing organic compound when fused with sodium metal forms:
(A) NaNO2 (B) NaCN (C) NaNH2 (D) NaNC
185. The sodium extract of an organic compound on acidification with acetic acid and addition of lead
acetate solution gives a black precipitate. The organic compound contains
(A) Nitrogen (B) Halogen (C) Sulphur (D) Phosphorus
186. Quinine is the most important alkaloid obtained from Cinchona bark. It’s molecular formula is
C20H24N2O2. It may contain
(A) 5 double bond & 6 ring (B) 6 double bond & 4 ring
(C) 6 double bond & 3 ring (D) 7 double bond & 5 ring

187. H / Ni Q
2

Which of the following is the correct statement about P & Q.

(A) Product will be 1-Methyl-3-(2-methylpropyl)cyclohexane.
(B) Product will be 3-Methyl-1-(2-methylpropyl)cyclohexane.
(C) DU of reactant P is 3.
(D) DU of product Q is zero.

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188. Which alkyne will gives 3-Ethyl heptane on catalytic hydrogenation.

(A) (B) (C) (D)

189. An alkane with the molecular formula C7H16 forms seven monochlorinated products. The name of the
alkane is :
(A) Heptane (B) 2-Methylhexane (C) 3-Methylhexane (D) 2,3-Dimethylpentane

Cl / h
190. X 2 4-structural products. Identify 'X'

(A) (B) (C) (D)

191. How many products (structural isomers only) are formed by monochlorination of given compound?

(A) 6 (B) 7 (C) 8 (D) 9

192. Carbon chain splits into two or more parts by ozonolysis from all except :
(A) 1, 3-Cyclobutadiene (B) 1, 2-Dimethylcyclohex-1-ene
(C) Benzene (D) Isobutene

Ozonolysis
193 An alkene (A)     , A is :

(A) (B) (C) (D)

194. For the following reactions sequence

OHC CHO
O3
Zn/H2O
The structures of X and Y are :
X Y X Y

(A) (B)

(C) (D)

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195. The chemical reactions of an unsaturated compound ‘M’ are given below. Determine the possible
structural formula of ‘M’

(M)

(A) (B) (C) (D)

O O O
O / Zn, H2O
|| || ||
196. X 3    H – C – CH2 – C – CH2 – C – H + HCHO
The structure of X will be :

(A) (B) (C) (D)

197.

Compound 'X' is :
(A) 1-Methylcyclopropene (B) 1, 4-Dimethylcyclohexa-1,4-diene
(C) 1, 4-Dimethylcyclohexa-1,3-diene (D) 1, 2-Dimethylcyclohexa-1,4-diene
198. Compound ‘A’ (C16H16) on ozonolysis gives only one product ‘B’, (C8H8O). ‘B’ gives positive Iodoform
test and forms sodium benzoate as one of the product. Identify the structure of ‘A.
CH3 Ph
| |
(A) Ph – CH2 – CH = CH – CH2 – Ph (B) CH3  C  C  Ph

CH3
|
(C) Ph  C  C  Ph (D) Ph  CH  C – CH2  Ph
| |
CH3 CH3
199. Compound 'A' gives red precipitate with Cu2Cl2 / NH4OH solution and decolourises bromine water.
The compound 'A' can be :
(A) CH2  CH  C  CH3 (B) CH2  CH  C  H
|| ||
O O
(C) CH3 – C  CH (D) PhCHO

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200. I and II are homologues. These can be distinguished by using :

(A) Tollen’s reagent (B) 2, 4 – DNP (C) Baeyer’s reagent (D) I2 + NaOH
201. Observe the following compound and select +ve & – ve test respectively.

(A) + + + – (B) + + + + (C) + – + – (D) + – – +

202. Which gas is released when Acetamide reacts with NaOH ?
(A) CO2 (B) N2 (C) NH3 (D) COCl2
203. Aromatic primary amines can be distinguished from aliphatic primary amines by
(A) Tollen's test (B) Action on red litmus paper
(C) Azo dye test (D) Action with dil. HCl
204. An organic compound does not react appreciably with lucas reagent but give white precipitate with
Tollen’s reagent. Which is the possible structure of compound ?
(A) (B)
OH
(C) (D) CH2=C=CH–CH2–OH
205 How many structure isomers of molecular formula C5H10O give chloroform with NaOCl ?
(A) 2 (B) 3 (C) 4 (D) 5
206. A organic compound (C6H8) gives only symmetrical diketone on ozonolysis. The product diketone
gives 2,4-DNP test but does not give iodoform test. Structure of organic compound can be :

(A) (B) (C) (D)

207. (x) C7H12 P+Q

H2O2
Compound P responds to Tollen’s test and NaHCO3 test but Q does not respond with both the
reagents. Structure of compound (P) is :
CH3 CH–CH3 CH2
(A) (B) (C) (D)
Cu2Cl2
208. Red precipitate P(C5H8) Ozonolysis 2-Methylpropanoic acid + compound (Q)
NH4OH
structure of P can be :
(A) CH3–CH2–CH2–CCH(B) (C) CH3CC–CH2–CH3 (D) CH 3–CH–CH=CH 2
CH3 CH3
209. A alkene on ozonolysis give only one product(x). x does not respond with Tollen’s reagent and NaOI
but give yellow precipitate with 2,4-DNP, The structure of alkene can be-

(A) (B) (C) (D)

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EXERCISE-2 (EXERCISE FOR JEE ADVANCED)
1. Ketones do not reduce Tollen’s reagents, but fructose with a keto group reduces it. It is attributed to
(A) Enolisation of keto group of fructose and then, its transformation into aldehyde group in presence
of OH¯ which is present in Tollen’s reagent
(B) > CHOH group which is also oxidised to keto group
(C) Both statements are correct
(D) None of the statement is correct
2. Haworth’s projection of -D glucose is :

(A) (B) (C) both (D) none

3.

On acid hydrolysis of above disacharide, we get

(A) Two moles of glucose (B) one mole of glucose
(C) One mole of galactose (D) one mole of glucose and one mole of galactose
4. Which is correct structure of -D-glucopyranose.

(A) (B)

(C) (D)

5. The structure of the following polymer is :

(A) Starch (B) Sucrose (C) Cellulose (D) Maltose

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6. In osazone formation of three molecules of phenylhydrazine which is the correct statement
(A) All the three molecules react in similar manner
(B) Two molecules reacts in similar manner whereas the third reacts in different way
(C) All the three molecules react in different way
(D) Only two react in same manner but the third molecules remains unreacted
7. Find the pair which is correctly matched
(A) Sucrose : monosaccharide (B) Fructose : aldose sugar
(C) Glucose : mutarotation (D) Sucrose : reducing sugar
8. Two hexoses form the same osazone find the correct statement about these hexoses.
(A) Both of them must be aldoses
(B) They are epimers at C-3
(C) The carbon atoms 1 and 2 in both have the same configuration
(D) The carbon atoms 3, 4 and 5 in both have the same configuration
9. Nitrous acid (HNO2) converts amino acids into hydroxy acids with retention of configuration.
Estimation of nitrogen gas evolved in the reaction is the basis of Van slyke estimation of amino
acids.
NH2 OH
HNO2
R – CH – COOH R – CH – COOH + N 2 + H 2O
Which of the following amino acids cannot be analysed by Van slyke method?
NH2

I – HS – CH2 – CH – COOH (cysteine)

N COOH
II – (Proline)
|
H
NH2

CH2 – CH – COOH
III – (Histidine)
H–N N

NH2

CH3 – CH – CH – COOH
IV – (Valine)
CH3
(A) only I (B) only II (C) I and III (D) I, III, IV

NH 2 NH2
10. CH 3 – CH – COOH 
( X)
 CH 3 – CH – CH 2OH

The reagent (X) can be

(A) H2 / Pd/BaSO4/quinoline (B) NaBH4 (C) LiAlH4 (D) CH3MgI

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HOOC – CH2 CH2 – Ph

11.
H2N – CH – CO – NH – CH – COOCH3
(Aspartame)
Aspartame is 160 times as sweet as sucrose and is used as a sugar substitute.
the correct statement (s) about aspartame is (are)
I – It is an ester derivative of dipeptide
II – It can be named as aspartyl phenylalanine methyl ester
III – It is a tripeptide
IV – It is having four functional groups.
(A) I, II (B) I, II, IV (C) II, III, IV (D) only II
12. The polymerisation reaction shown below
(1) CH MgCl
CuCl
2 CH  CH   CH  C – CH = CH 2 CH2  C – CH  CH2   3 
| ( 2 ) Polymerisation
Cl
 – CH2 – C  CH – CH2 
 
 | 
 CH3 
n
would produce :
(A) PVC (B) neoprene (C) chloroprene (D) Rubber

13. Which of the following is radical initiator

(A) R – N = N – R (B)

(C) (D) All

HOH2C CH2OH
N–C–N
14. || CH2OH
HOH2C
O
The polymer obtained by the above compound is
(A) Bakelite (B) Urea formaldehyde resine
(C) Melamine formaldehyde resin (D) Tefflon
15. Which of the following contains isoprene unit?
(A) Natural rubber (B) Polyethylene (C) Nylon – 66 (D) Dacron
16. Which of the following polymerises most easily ?
(A) CH3CH2CCH (B) CH2=CH–CH=CH2 (C) CH3CH2–CH=CH2 (D) CHC–CCH
17. Which of the following is condensation polymer?
(A) Polystyrene (B) PVC (C) Polyester (D) Teflon
18. Carbohydrates contain ?
(A) –OH group (B) –CHO group (C) >C=O group (D) All

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19. Which of the following monosaccharide is pentose ?
(A) Glucose (B) Fructose (C) Arabinose (D) Galactose
20. On heating glucose with Fehling solution. We get a precipitate whose colour is ?
(A) Yellow (B) Red (C) Black (D) White
21. Which of the following compounds is found abundantly in nature ?
(A) Fructose (B) Starch (C) Glucose (D) Cellulose
22. Glucose on reduction with Na/Hg and water gives ?
(A) Sorbitol (B) Fructose (C) Saccharic acid (D) Gluconic acid
23. Glucose or fructose is converted into C2H5OH in the presence of ?
(A) Diastage (B) Maltase (C) Invertase (D) Zymase
24. Glucose cannot be calassified as ?
(A) Hexose (B) Carbohydrate (C) Aldose (D) Oligo saccharide
25. Milk sugar is commonly known as
(A) Maltose (B) Lactose (C) Fructose (D) Glucose
26. The commonest disaccharide has the molecular formula ?
(A) C10H18O9 (B) C10H20O11 (C) C18H22O11 (D) C12H22O11
27. Strach is changed into disaccharide in presence of ?
(A) Diastase (B) Maltase (C) Lactase (D) Zymase
28. Which carbohydrate is used in silvering of mirror ?
(A) Sucrose (B) Fructose (C) Glucose (D) Strach
29. The charring product when C6H12O6 is heated with conc. H2SO4 is due to ?
(A) Oxidation (B) Reduction (C) Dehydration (D) Dehydrogenation
30. A certain compound give negative test with ninnydrin, but positive test with benedict solution. The
compound is ?
(A) Protein (B) Monosaccharide (C) Lipid (D) Amino acid
31. It is best to carry out reaction with sugers in neutral or acidic medium and not is alkaline medium
because in alkaline medium sugars undergo ?
(A) Racimisation (B) Decomposition (C) Inversion (D) Rearrangement
32. The reagent which forms crystalline osazone derivatives when heated with glucose is ?
(A) Fehling solution (B) Phenyl hydrazine (C) Benedict solution (D) Hydroxyamine

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33. Consider following reagent :
I. Br2 water II. Tollen’s reagent III. Fehling’s solution
which can be used to make distinction between an aldose and a ketose ?
(A) I, II and III (B) II and III (C) I only (D) II only
34. The organic compound that will response Fehling’s solution test is
(A) Ethanol (B) Acetone (C) Maltose (D) Benzaldehyde
35. In a-D-galactopyranose the vicinal hydroxyl groups are cis to each other -

Product

The product may be :

(A) (B)

(C) CH3COOH (D)

36. How many cyclo alkenes (structural only) on hydrogenation can give following compound.

(A) 7 (B) 8 (C) 9 (D) 10

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37. If 1 mole H2 is reacted with 1 mole of the following compound.

Which double bond will be hydrogenated ?

(A) c (B) b (C) a (D) d
38. An alkane which forms a single monochlorinated product after monochlorination. The alkane is :
(A) Neopentane (B) Hexamethyl cyclopropane
(C) Tetramethyl butane (D) All of these
39. Compound ’A’ (C3H6O), decolourizes Br2 water. It liberates colourless, odourless gas on addition of
sodium metal. On ozonolysis, it gives B and compound ‘C’ (C2H4O2). Identify ‘A’.

(A) (B) CH2=CH–CH2OH (C) (D) CH3–CH2–CHO

40. An hydrocarbon on oxidative ozonolysis produces oxalic acid and butanedioic acid. Its structure is

(A) (B) (C) (D)

41.

Number of Z are :
(A) 2 (B) 3 (C) 4 (D) 5
H2/Ni O3/H2O2
42. X Y Two carbon carboxylic acid and Four carbon ketone
Cl2/h
Z-products (Consider only structural Isomer)
The value of Z is :
(A) 4 (B) 6 (C) 7 (D) 8

Cl / h 
43.  2   products (only structural isomers).
monochlori nation

(A) 5 (B) 4 (C) 3 (D) 2

44. Ozonolysis of Agathene dicarboxylic acid gives

CHO
, H2CO & |
COOH

Structure of Agathene dicarboxylic acid should be ?

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(A) (B)

(C) (D)

45. Farnesene is a compound found in the waxy coating of apples. On hydrogenation it gives 2, 6,
10-trimethyl dodecane. On ozonolysis it gives one mole acetone, one mole of formaldehyde, one
mole of 2-methylpentanedial and one mole of 4-oxopentanal. The structure proposed for farnesene
may be

(A) (B)

(C) (D)

46. A compound P(C5H6) gives Bayer test positive and on hydrogenation from a hydrocarbon B(C5H10)
which gives only one monochloro product. The compound 'P" is.

(A) (B) (C) (D) CHC–CH2–CH=CH2

47. In compound A (C30H60O) following tests are observed negatively, A can be

(A) an unsaturated ether (B) an epoxide

(C) a cyclic ketone (D) a cycloalkanol
48. When a primary amine is warmed with carbon disulphide in the presence of mercuric chloride, the
product is
(A) Carbylamine (B) Alkyl isothiocyanate (C) Mercaptan (D) Alkyl cyanide
49. An aromatic amine (X) was treated with alcoholic potash and another compound (Y) then foul smelling
gas C6H5NC is formed. The compound (Y) was formed by reacting compound (Z) with Cl2 in the
presence of slaked lime. The compound (Z) is :
(A) CHCl3 (B) CH3COCH3 (C) CH3OH (D) C6H5NH2
50. Compound A (C3H5N) gives precipitate with Tollen’s reagent and H2 gas is also evolved on addition
of Li metal. Compound A can be :
(A) CH3–CH2–CN (B) H–CC–NH–CH3 (C) CH3–CH2–N C (D) CH2=C=N–CH3

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51. Compound C4H10O (Structural)

Compound is

(A) (B) (C) (D)

O3 Molish
52. C8H16O6(P) C4H8O4(Q) Violet colour ring
Zn, H2O reagent
Structure of P can be -
OH

(A) CH2–CH–CH–CH=CH–CH–CH–CH2 (B) HO OH

OH OH OH OH OH OH OH
OH OH
(C) CH2–CH–CH–CH=CH–CH–CH–CH=O (D) HOOC–CH2–CH–CH=CH–CH–CH2–COOH
OH OH OH OH OH OH OH

53. Which of the following compound can prepared Iodoform when react with OI–(hypoiodite)
(A) (B)

(C) (D)

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ONE OR MORE THAN ONE CHOICE CORRECT
1. The correct statement (s) about starch
(A) It is a pure single compound
(B) It is mixture of two polysaccharides of glucose
(C) It involves the (C1 – C4) -glycosidic linkage between two  - D glucose units
(D) It involves branching by (C1 – C6) glycosidic linkage

2. (I) (II) (III)

The correct statement about the sugars given above are

(A) I and II are L-Sugars (B) II and III above D-Sugar
(C) I and III are D-sugars (D) I is L-sugar

3. Glucose

The correct statements about above structure of glucose are :

(A) It is a Pyranose form (B) It is a furanose form
(C) It is a -anomer (D) It is a D -sugar
4. D-Mannose differs from D-glucose in its stereochemistry at C-2. The pyranose form of D-Mannose
is

(A) (B) (C) (D)

5. The correct statements about anomers are

(A) Anomers have different stereochemistry at C-1(anomeric carbon)
(B) -D-glucopyranose and -D-glucopyranose are anomers
(C) Both anomers of D-glucopyranose can be crystallised and purified.
(D) When pure -D-glucopyranose is dissolved in water its optical rotation slowly changes
6. The correct statements about peptides are
(A) A dipeptide has one peptide link between two amino acids.
(B) By convention N-Terminus is kept at left and C- terminus at right in the structure of a peptide
(C) If only one amino group and one carboxylic acid, group are available for reaction, then only one
dipeptide can forms.
(D) A polypeptide with more than hunderd amino acid recidues (mol. mass > 10,000) is called a
protein
7. Which of the following are polyamide polymer ?
(A) Protein (B) Nylon–6,6 (C) Nylon–6 (D) Polystyrene
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8. Which of the following is /are reducing sugar
(A) Sucrose (B) Glucose (C) Fructose (D) methylmaltoside

NaBH
9. 4
  A +B

The product A and B in the a above reaction are

(A) Diastereomers (B) C-2 epimers
(C) Anomers (D) Optically active hexahydroxy compounds
10. Which of the following pairs is (are) correctly matched
(A) - D (+) glucose and -D(+) glucose  C-2 epimers
(B) Glucose and fructose  C-3 epimers
(C) Glucose  mutarotation
(D) Sucrose  Glucose + fructose
11. Which of these are polysaccharides of glucose ?
(A) Starch (B) Cellulose (C) Sucrose (D) Lactose
12. The correct structure of glycine at given pH are :

(A) at pH = 2.0 (B) at pH = 6.0

(C) at pH = 9 (D) at pH = 12

13. Preparation of nylon from hexamethylene diamine and adipic acid is an example of :
(A) addition polymerisation (B) homopolymerisation
(C) condensation polymerisation (D) copolymerisation

14. Structures of some common polymers are given. Which are correctly presented ?

(A) Teflon ( CF2  CF2 –)n (B) Neoprene   CH2  C

|
 CH  CH2  CH2  

 Cl 
 n

(C) Terylene (D) Nylon-66 [ NH(CH ) NHCO(CH ) –CO–]

2 6 2 4 n

15. Alaskene is the fragrant oil having structure as below :

CH3

H3C C
CH3 CH3
Which is/are true about this compound
(A) Its DU = 4

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(B) After hydrogenation its chlorination gives 13 monochloro products
(C) For hydrogenation it requires 2 mol of H2
(D) On ozonolysis it gives ketone only

16. Which will perform iodoform reaction with I2/OH– ?

(A) CH3COCH2CH3 (B) CH3CONH2 (C) C6H5COCH3 (D) CH3CHO

17. Correct statement about is :

(A) It gives coloured solution with neutral FeCl3 solution. (B) It liberates one mole H2 gas with Na
metal.
(C) It gives CO2 gas with NaHCO3. (D) It forms sweet smelling compound with
alcohols.

18. Correct statement about is :

(A) It gives coloured solution with neutral FeCl3 solution. (B) It liberates half mole H2 gas with Na
metal.
(C) It gives +ve Iodoform test. (D) It forms sweet smelling compound with
alcohols.

19. Correct statment about is :

3
(A) librate mole of H2 on treatment with Na. (B) Positive test with FeCl3
2
(C) Positive test with NaHCO3 (D) Positive test with tollen's reagent

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COMPREHENSION TYPE

Read the following passage carefully and answer the questions.

Comprehension # 1

HIO 4
[X] Pmole


Hydrolysis
[X]   [Y] + [Z]


3 PhNHNH2 / H
(Y or Z)       + PhNH2 + NH3

1. Compounds Y and Z can be :

(A) 1 only (B) 2, 3 (C) 1, 4 (D) 2, 3, 4

2. Number of moles (P) of HIO4 used per moles of compound X is :
(A) 2 (B) 3 (C) 4 (D) 5

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Comprehension # 2
Proteins are biomolecules composed of -amino acids. An -amino acid has a general formula
R  CH  COOH . The amino acids polymerise and form an amide linkage (peptide linkage) between
|
NH2
two monomeric amino acid units. The polymerisation takes place as follows

Two or more similar amino acids can also polymerise, for example a dimer will be like

R R
| |
H2N  CH  C  NH  CH  C  OH
|| ||
O O

3. In the above trimer, if R1 = H ; R2 = CH3 & R3 = Ph

then total number of optically active stereoisomers will be :
(A) 8 (B) 6 (C) 4 (D) 2
4._ In the given trimer if R1 = H ; R2 = CH3 and R3 = Ph
then the amino acids present in the trimer are :
(A) Glycine, Alanine & Phenyl Alanine (B) Glycine, Leucine & Phenyl Alanine
(C) Alanine, Valine & Phenyl Alanine (D) Alanine, Leucine & Lysine
5. Which statement is incorrect about the given trimer.
(A) it will liberate CO2 with NaHCO3.
(B) It will liberate N2 with NaNO2 / HCl
(C) It will give yellow precipitate with 2, 4-Dinitrophenylhydrazine
(D) It will rotate plane polarized light.

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Comprehension #3
A compound (P) having molecular formula C6H10 contains two DU. It yields Q(C6H12) when reacts
with excess of H2 in the presence of Ni. On ozonolysis P gives cyclopentanone and compound Y.

6. Identify the structure of the compound P

(A) (B) (C) (D)

7. The compound Q gives the number of monochlorination products

(A) 3 (B) 4 (C) 5 (D) 6

8.. Which of the following are not F.G. isomers of cyclopentanone

(A) (B) (C) (D)

MATCH THE COLUMN

1. Match Column-I with Column-II.
Column-I Column-II
(polymer) (monomer)
(A) Bakelite (p) - caprolactum
(B) Polypropylene (q) Ethylene glycol + phthalic anhydride
(C) Glyptal (r) propene
(D) Nylon-6 (s) Phenol + formaldehyde
2. Match the Following :
Column I Column II
(Artificial sweetners) (Characteristics)

(A) (p) A derivative of dipeptide

(B) (q) A derivative of disaccharide

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(C) (r) Reduction prouct of an aldopentose

(D) (s) Oxidation product of aldohexose

3. Match the column %

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4. Match the compounds of column – I with the reagent of column – II.
Which can distinguish between the compounds of column I
Column – I Column – II
(A) , (p) Tollen’s reagent

(B) , (q) I2/NaOH

(C) , (r) Lucas reagent

(D) , (s) neutral FeCl3

(t) 2,–DNP
5. Column-I Column-II
(A) CH3–CH=CH–CH2– C –CH3 (p) Bromine water solution decolourised
||
O

(B) (q) precipitate obtained with AgNO3 + NH4OH

(C) (r) CO2 gas liberated by NaHCO3

(D) (s) Yellow precipitate by 2, 4-DNP

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SUBJECTIVE QUESTIONS
1. What are monosaccharides ?
2. What are reducing sugars ?
3. What do you understand by glycosidic linkage ?
4. What are the hydrolysis products of sucrose ?
5. What is the basic structural difference between starch and cellulose ?
6. Write the reaction of D - glucose with HNO3
7. Give reasons as the evidence in support of cyclic structure of glucose
8. What is mutarotation ?
9. Simple six memebered ring compound (eg. Cyclohexane) are not soluble in water whereas glucose
and sucrose are soluble in water. Explain why ?
10. The fischer projection of D-fructose is given below, write the fischer projection of L-fructose.

11. The melting point and solubility (in H2O) of amino acids are generally high. explain why ?
12. What do you mean by the following also give example
(a) Non -essential amino acids (b) Essential amino acids
13. Amino acids show amphotric behaviour . Explain why ?
14. Why an amino acid is usually solid at room temperature.
15. How will you identify a basic amino acid ?
16. What is the product obtained when glycine hydrochloride reacts with two equivalents of NaOH ?
Write the chemical reactions involved.
17. Tyrosine is an  –amino carboxylic acid shown below:

Write the most stable structural formula ;

(a) In it’s cationic form (b) In it’s anionic form
(c) In it’s dianionic form (d) In it’s Zwitterionic form
18. What is the denaturation of proteins ?
19. What is the difference between Buna-N and Buna-S
20. Arrange the following in the increasing order of their intermolecular forces
Nylon 6, Neoprene, Polyvinyl chloride
(I) (II) (III)
21. Classify the following as addition and condensation
polymers : Terylene, Bakelite, polyvinyl chloride, polythene

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22. What is copolymerisation give two examples.
23. The partial structure of neoprene, a polymer is given below. Identify the monomer unit.

24. Classify the following monosaccharides in proper aldoses and ketose.

(i) (ii) (iii) (iv)

25. Write the anomer and epimer, enantiomer and ketose of the following aldose, also mention whether
these are L sugars or D sugars .

L-aldopentose
26. Draw two anomers of D-fructose.
27. The specific rotation of two glucose anomers are  = + 110º and  = +19º and for the constant
equilibrium mixtures is +52.7º. Calculate the percentage compositions of the anomers in the
equilibrium mixture.
28. Consider an amylose chain of 4000 glucose unit. At how many cleavage require to lower the average
length to 400 units.

29. (A)

Predict (A) :

30. A + 4HIO4  3HCOOH + HCHO + OHC – COOH

B + 5HIO4  4HCOOH + 2HCHO

Identify A and B.
31. On reduction of a monosaccharide A (C4H8O4) mixture of two epimeric alcohols B & C is formed.
(a) Monosaccharide has aldehyde or ketone group ?
(b) Determine the structures of A , B and C.

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32. On which side of neutrality (pH–7) , the isoelecric point of the following amino acids will lie ?
(a) H – CH – COOH (b) H2N – CH – COOH (c) H2N – CH – COOH
| | |
NH2 CH 2 – CH 2 – COOH (CH2 ) 4 – NH2
33. Glutamic acid (A) has isoelectric point 3.22
(a) What is the most likely structure of the compound at its isoelectric point ?
(b) What is the most likely structure of mono sodium glutamate.
H2N  CH  COOH
|
CH2  CH2  COOH
( A)
34. A polypeptide (Mol. wt = 360) formed by glycine (Mol. wt. = 75) amino acid. How many glycine units
are used to form it.
35. 0.89 g of an  –amino acid (A) gave 0.224 lit. N2 gas at NTP on reaction with HNO2. In this process
an opticallly active acid (B) is formed. A as well as B, gave cyclic compouns C and D on intermolecular
dehydration. Identify A to D.
36. Hydrolysis of the following compound (A) in conc. HCl for several hours at 373K gives an amino acid
. Identify it . Is it optically active ?

(A)

37. Distinguish between

(a) Glycine and acetamide (b)  – ,  – & – amino acids.

38. An octapeptide (Mol. wt. = 516 g) on complete hydrolysis given glycine and alanine (Mol. mass = 89
g). Alanine contributes 41.59% to total weight of hydrolysed product. How many number of alanine
unit present in octapeptide.

39. Give the amino acid sequence of the following polypeptides using the data given by partial hydrolysis.
H O
(a) (Ser,Hyp,Pro,Thr) 3 Ser, Thr + Thr, Hyp + Pro, Ser
H O
(b) (Ala, Arg,Cys,Val,Leu) 3 Ala, Cys + Cys, Arg + Arg, Val + Leu, Ala

O H
|| |
40. Glutamic acid has lower isoelectric point while glutamine H2N  C  CH2  CH2  C  COOH has higher
|
NH2

isolectric pH. Explain ?

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41. Give the following conversion acetaldehyde  alanine

42. Complete the following reactions

(a) + CH2  CH – C  N 150º C

  (a copolymer)

(C6H5 COO)2 , 
(b) +         a cross linked copolymer

43. Write the structures of monomers of the following polymers.

(a) (b) (c)

44. Fill in the blanks

A sugar in which an amino group replaces the anomeric –OH is called glycosylamine. Also a sugar
in which an amino group replaces a nonanomeric –OH is called an amino sugar.
Fill the correct answer (glycosylamine/amino sugar) in the blanks and complete the statements

(i) is an example of ............

(ii) is an example of .............

(iii) is an example of ............

45. Draw fischer projections for the two D–aldoheptoses whose stereorientation at C2, C3, C4, C5 is
same as that of D–glucose at C2,C3,C4 and C5.

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46. How many aldoheptoses are there ? How many are D-sugars & how many are L-sugars ?
47. Aldoses give positive Tollen’s, Fehling’s and Osazone reactions but fail to respond Schiff’s and
bisulphite test.
48.  -glucose is oxidized by HIO4 more rapidly than is  -anomer at the 1-2 bond.
49. Reduction of L-glucose with NaBH4 leads to the same alditol glucose as reduction of D-glucose.

50. When CH3OH reacts with glucose two types of glucoside are obtained. Why is it so ?

51. Reduction of D-glucose forms D-sorbitol while that of D-fructose forms a mixture of D-sorbitol and
D-mannitol.

52. Unlike glucose, neither  -nor  -methyl glucoside reduces Tollen’s reagent or Fehling solution. Why
?

Ac 2O
53. (+)-Glucose   (A) + (B)   (negative). Give reasons.
AgNO 3 / NH4 OH
  

54. Both glucose and fructose are reducing sugars but sucrose is non reducing in nature. Why ?

55. Why is D-fructose used for sweetening cold drinks but not hot ones ?

56. What would be the molecular formula of (+) -sugar if C – 1 of glucose is attached to C – 4 of fructose
and C – 2 of fructose is attached to C – 4 of glucose ? Would this be a reducing sugar ?

57. When (+) sucrose is hydrolysed, the D-glucose mutarotates downward to + 52.7°. What does this
indicate about the structures of (+) -sucrose ?

How will you distinguish between :

58. Glucose and glycine.

59. Glucose and fructose

Amino acid
Complete the following reactions :

60. R – CH – COO ¯ HCl(aq)

  
|
NH2

61. R – CH – COOH NaOH (aq)

   
|

NH3

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62. HOOC – CH2 – CH – COOH NaOH (aq)

   
|

NH3

63. NaOH(aq)
   


(CH2 ) 4 NH3
 | NaOH NaOH NaOH
64. H3 N– CH – COOH      A   B   C

KCN  NH 4 Cl 3 H O
65. A      B   alanine

66. Ala, Gly

LiAlH 4 PCl 5 KCN H O

67.     A    C 3 D
 B  

O
|| (i) NH /  HNO 2
68. 3 
CH3 – C – C – OH        
|| (ii ) NaBH
4
O

NBS KCN OH /  P / Br2 NH3 

69. CH3CH = CH2    B   
 A    C   E  F
 D  

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O
||
CH2 CH2CH2 – C – OH  LAH
70.  A  
 B
|
NH2

1 equiv . HCl
71. Phenyl alanine + NaOH  A     
 B

72. (A) (B) (C)

(R, S mixture) (S–amino acid) (R–amino acid)

1.EtONa
73. +  A     
2.Br (CH2 )3 Br

NaOH , 
HCl D (C H O N) 
E (C5H10O2NCl) Proline  5 11
1 3    C (C20H23O8N)

H ,

O
||
74. Ph – CH – C – NH – CH – COO ¯ + (1) base,  ( 2) H O  , 
     3   
| |

NH3 CH3

75. (a) Write the structures of alanine at pH = 2 and pH = 10

(b) Identify A, B and C and give their structures.

Br2 H
  A + B 
 C(C7H12O)
NaOH 

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76. Give the structure of each of the products in the following reaction

H
(i)  A + B
Sucrose 

 Polymerisa tion
H
(ii)  C  
  [– D –]n

77. How many isomeric alkynes on catalytic hydrogenation gives 3-Ethyl - 4-methylheptane.

78. How many alkene, alkyne, alkadienes can be hydrogenated to form Isopentane (Including all structural
isomers)

79. How many isomeric alkenes gives 2, 3, 4-Trimethylpentane after hydrogenation.

80. Write the products of following reactions :

H / Ni
(i) 2,3,3-Trimethylbut-1-ene 2  product.
H / Ni
(ii) 2-Methylbut-1-ene 2  product.

H / Ni Cl / h
81. 2 
 P 2 Q (Total number of monochloro structural products).

82.
Number of structural monochloroination product of above compound is :

83. How many alkenes yield 2, 2, 3, 4, 4-pentamethylpentane on catalytic hydrogenation ? Draw structural
formula of these alkenes. How many monochloro isomers are possible for this compound (2, 2, 3, 4,
4-pentamethylpentane)

84. Find the structural isomers of fully saturated Cycloalkane of M.F. C6H12 which gives three monochloro
products?

85. Compound ‘A’ (C5H10) on ozonolysis gives two compounds D and E. Both D, E give positive Iodoform
test. E responds to Tollen’s test but D does not. Identify the structure of A, D and E.

86. Identify the structure of compound (X) having molecular formula C10H14 that is hydrogenated with
three equvalent of H2/Pd to give 1-isopropyl-4methyl cyclohexane and on reductive ozonolysis gives
the following products.
H – C – H + OHC – CH2 – C – C– CH3 + CH3 – C – CH2 – CHO
O O O O

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87. How many functional groups which react with Tollen's reagent (Ammonical silver nitrate).

88. How many moles of H2 will liberate when 1 mole of the following compound reacts with Sodium.

89. Find the structure of ‘X’

90. The total number of structural possible for a compound with the molecular formula C6H12O which
can give positive iodoform and 2,4-DNP test is :

91. An alcohol gives Lucas test within 5 min, 6gm of it when treated with sodium metal liberates 1120ml
of H2 at STP. Write the structure of alcohol ?

92. Tick mark the reagent which will give positive response with following compound :

(1) Na–metal (2) NaHCO3 (3) 2,4-DNP

(4) AgNO3 + NH4OH (5) Fehling solution (6) NaNO2 + HCl
(7) ZnCl2 (anhydrous)/HCl (8) Cu2Cl2 + NH4Cl (9) Br2/H2O (10) Dil KMnO4 (cold).

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93. A Hydrocarbon P(C9H16) on ozonolysis gives three products Q, R & S. Q & R are isomers. All the
three products contain three carbon atom. write the structure of hydrocarbon P is.

94. How many no. of active Hydrogen atoms are present in a compound (mol.mass 90) 0.45 g of which
when treated with Na metal liberates 112 ml of the H2 gas at STP.
95. How many structural isomeric cycloalkene on hydrogenation can give following cycloalkane.

96. Write total number of monochloro (Strcutural) products of following compounds :

(i) (ii) (iii) (iv)

97. How many moles of 2,4-Dinitrophenyl hydrazine will be used to react completely with 1 mole of the
given compound?

98. Three isomeric alkenes (P, Q, R) having molecular formula (C5H10) gives same alkane (X) on
hydrogenation. Find the no. of monochloro products of alkane (X) and write the structures of P, Q
and R.

99. A Hydrocarbon X(C6H12) on reductive ozonolysis gives only one product Y (C3H6O). Y gives yellow
precipitate with NaOI, while X on hydrogenation gives an alkane Z (C6H14) which on monochlorination
gives two structure isomers as product. Identify X, Y, Z and write equations.

100. An organic compound E(C5H8) on hydrogenation gives compound F(C5H12). Compound E on

ozonolysis gives formaldehyde and 2-ketopropanal. Identify the structure of compound E.

101. A compound "M" (C10H20) gives a product “P” on hydrogenation which has only 2 monochloro struc-
tural isomeric products when treated with Cl2/hIf “M” is ozonolysed in presence of zinc, “W” is the
only product obtained. Write all the equations.

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102.

Calculate sum of number of products formed in the reaction a, b and c.

103. C5H12O2 gives instant turbidity (white thin precipitate) with anhydrous ZnCl2 / HCl and with sodium
metal 1 mole of compound liberates 11.2 litre H2 gas at STP. write the structure of molecule ?

104. A chloro compound (A) showed the following properties.

(1) Decolorised bromine in CCl4. (2) Absorbed hydrogen catalytically.
(3) Gave a precipitate with ammonical cuprous chloride.
(4) When vapourised 1.49 g of (A) gave 448 ml of vapours at STP.
Identify (A) and write down the equation of reactions.

105. Identify the structure of A :

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EXERCISE-3 (IIT JEE PREVIOUS YEAR'S QUESTIONS)

1. Aspartame, an artificial sweetener, is a peptide and has the following structure :

CH2C 6H5
|
H2NCH  CONH  CH  COOCH3
|
CH2  COOH

(i) Identify the four functional groups

(ii) Write the zwitter ionic structure
(iii) Write the structures of the amino acids obtained from the hydrolysis of aspartame.
(iv) Which of the two amino acids is more hydrophobic ?
2. Following two aminoacids leusine and glutamine form dipeptide linkage. What are two possible
dipeptides ?

(CH3 )2 CHCH2CHCOOH and H2NCOCH2CH2  CHCOOH

|
| NH2
NH2
3. Write down the heterogenous catalyst involved in the polymerisation of ethylene.
4. Which of the following pairs give positive Tollen’s Test ?
(A) Glucose, sucrose (B) Glucose, fructose (C) Hexanol, Acetophenone (D) Fructose,sucrose
5. The Fischer projection formula of D-glucose is
(i) Give Fischer projection formula of L-glucose.
(ii) Give the product of reaction of L-glucose with Tollen’s reagent.
6. The two forms of D-Glucopyranose obtained from solution of D-Glucose are known as
(A) Epimers (B) Anomers (C) Enantiomers (D) Geometrical Isomers
7. Which of the following disaccharide will not reduce tollen's reagent.

CH2OH CH2OH CH2OH CH2OH

O O O O
HO H H OH HO H H OH
H H H H
H H OH O H OH H H OH O OH H
H H
OH H OH H OH H H OH

P Q

8. Match the chemical substances in Column-I with type of polymers/type of bonds in Column-II.

Column-I Column-II
(A) cellulose (p) natural polymer
(B) nylon-6, 6 (q) synthetic polymer
(C) protein (r) amide linkage
(D) sucrose (s) glycoside linkage

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9. Statement-1 : Glucose gives a reddish-brown precipitate with Fehling's solution.
because
Statement-2 : Reaction of glucose with Fehling's solution gives CuO and gluconic acid.
(A) Statement-1 is True, Statement-2 is True; Statement-2 is a correct explanation for Statement-1.
(B) Statement-1 is True, Statement-2 is True; Statement-2 is NOT a correct explanation for Statement-1
(C) Statement-1 is True, Statement-2 is False
(D) Statement-1 is False, Statement-2 is True
10. Cellulose upon acetylation with excess acetic anhydride/H2SO4 (catalytic) gives cellulose triacetate
whose structure is

(A) (B)

(C) (D)

11. Among celluose, poly vinyl chloride, nylon and natural rubber, the polymer in which the intermolecular
force of attraction is weakest is :
(A) Nylon (B) Poly vinyl chloride (C) Cellulose (D) Natural Rubber
12. The correct statement(s) about the following sugars X and Y is(are) :

(A) X is a reducing sugar and Y is a non-reducing sugar.

(B) X is a non-reducing sugar and Y is a reducing sugar.
(C) The glucosidic linkages in X and Y are  and , respectively.
(D) The glucosidic linkages in X and Y are  and , respectively.
13. A decapeptide (Mol. Wt. 796) on complete hydrolysis gives glycine (Mol. Wt. 75), alanine and
phenylalanine. Glycine contributes 47.0 % to the total weight of the hydrolysed products. The number
of glycine units present in the decapeptide is

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14. The following carbohydrate is

(A) a ketohexose (B) an aldohexose (C) an -furanose (D) an -pyranose

15.* The correct functional group X and the reagent/reaction conditions Y in the following scheme are

condensation polymer :

(A) X = COOCH3, Y = H2/Ni/heat (B) X = CONH2, Y = H2Ni/heat

(C) X = CONH2, Y = Br2/NaOH (D) X = CN, Y = H2/NI/heat
16. When the following aldohexose exists in its D-configuration, the total number of stereoisomers in its
pyranose form is :

17. The substituents R1 and R2 for nine peptides are listed in the table given below. How many of these
peptides are positively charged at pH = 7.0 ?

Peptide R1 R2
I H H
II H CH3
III CH2COOH H
IV CH2CONH2 (CH2)4NH2
V CH2CONH2 CH2CONH2
VI (CH2)4NH2 (CH2)4NH2
VII CH2COOH CH2CONH2
VIII CH2OH (CH2)4NH2
IX (CH2)4NH2 CH3

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18. The total number of lone-pairs of electrons in melamine is
19. A tetrapeptide has – COOH group on alanine. This produces glycine (Gly), valine (Val), phenyl alanine
(Phe) and alanine (Ala), on complete hydrolysis. For this tetrapeptide, the number of possible
sequences (primary structures) with – NH2 group attached to a chiral center is :
20. Five isomeric para-disubstituted aromatic compounds A to E with molecular formula C8H8O2 were
given for identification. Based on the following observations, give structures of the compounds.

(i) Both A and B form a silver mirror with Tollen’s reagent; also B gives a positive test with FeCl3
solution.
(ii) C gives positive iodoform test.
(iii) D is readily extracted in aqueous NaHCO3 solution.
21. In conversion of 2-butanone to propanoic acid which reagent is used.
(A) NaOH, NaI / (B) Fehling solution (C) NaOH, I2 / (D) Tollen's reagent

(JEE MAIN PREVIOUS YEAR'S QUESTIONS)

1. A substance forms zwitter ion. It can have functional group.

(1) – NH2 , – COOH (2) – NH2 , – SO5H (3) Both (1) and (2) (4) None of these
2. Monomers are converted to polymers by
(1) Hydrolysis of monomer (2) Condensation between monomers
(3) Protonation of monomers (4) none
3. Complete hydrolysis of cellulose gives
(1) D-fructose (2) D-ribose (3) D-glucose (4) L-glucose
4. Nylon threads are made up of
(1) polyvinyl polymer (2) Polyester polymer (3) Polyamide polymer (4) Polyethylene polymer
5. Which of the following is a polyamide ?
(1) Bakelite (2) Terylene (3) Nylon-66 (4) Teflon
6. Which of the following is fully fluorinated polymer
(1) PVC (2) Thiokol (3) Teflon (4) Neoprene
7. The pyrimidine bases present in DNA are
(1) cytosine and guanine (2) cytosine and thymine
(3) cytosine and uracil (4) cytosine and adenine
8. The term anomers of glucose refers to
(1) a mixture of (D)glucose and (L)glucose
(2) enantiomers of glucose
(3) isomers of glucose that differ in configuration at carbon one (C1)
(4) isomers of glucose that differ in configurations at carbons one and four (C1 and C4)

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9. The secondary structure of protein refers to:
(1) -helical backbone. (2) hydrophobic interactions.
(3) sequence of -amino acids. (4) fixed configuration of the polypeptide backbone.
10. Bakelite is obtained from phenol by reacting with
(1) CH3CHO (2) CH3COCH3 (3) HCHO (4) (CH2OH)2
11. Buna-N synthetic rubber is a copolymer of :
(1) H2C=CH–CH=CH2 and H5C6–CH=CH2 (2) H2C=CH–CN and H2C=CH–CH=CH
Cl
|
(3) H2C=CH–CN and H2C=CH– C  CH2 (4) H2C=CH– C  CH2 and H2C=CH–CH=CH2
|
CH3
12. The two functional groups present in a typical carbohydrate are :
(1) –CHO and –COOH (2) >C=O and –OH (3) –OH and –CHO (4) –OH and –COOH
13. The polymer containing strong intermolecular forces e.g. hydrogen bonding is
(1) teflon (B) nylon 6,6 (3) polystyrene (4) natural rubber
14. The presence or absence of hydroxy group on which carbon atom of sugar differentiates RNA and
DNA.
(1) 1st (2) 2nd (3) 3rd (4) 4th
15. Synthesis of each molecule of glucose in photosynthesis involves :
(1) 18 molecules of ATP (2) 10 molecules of ATP
(3) 8 molecules of ATP (4) 6 molecules of ATP
16. On mixing a certain alkane with chlorine and irradiating it with ultraviolet light, it forms only one
monochloroalkane this alkane could be :
(A) propane (B) pentane (C) isopentane (D) neopentane.
17. The prussian blue colour obtained during the test of nitrogen by Lassaigne’s test is due to the formation
of :
(A) Fe4[Fe(CN)6]3 (B) Na3[Fe(CN)6] (C) Fe(CN)3 (D) Na4(Fe(CN)5NOS]
18. Of the five isomeric hexanes,the isomer which can give two monochlorinated compounds is ?

(A) n–Hexane (B) 2,3-Dimethylbutane

(C) 2,2-Dimethylbutane (D) 2-Methylpentane
19. Among the following the one that gives positive iodoform test upon reaction with 2 and NaOH is ?
(A) CH3CH2CH(OH)CH2CH3 (B) C6H5CH2CH2OH

(C) CH3  CH  CH3 (D) PhCHOHCH3

|
CH2  OH

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20. In the following sequence of reactions, the alkene affords the compound 'B'

O3 H O
CH3CH = CHCH3  A 2 B compound B is
Zn

(A) CH3CH3CHO (B) CH3COCH3 (C) CH3CH2COCH3 (D) CH3CHO

21. Which of the following reagents may be used to distinguish between phenol and benzoic acid ?

(A) Aqueous NaOH (B) Tollen's reagent (C) Molisch reagent (D) Neutral FeCl3
22. Silver Mirror test is given by which one of the following compounds?
(A) Acetaldehyde (B) Acetone (C) Formaldehyde (D) Benzophenone
23. Ozonolysis of an organic compound 'A' produces acetone and propionaldehyde in equimolar mixture.
Identify 'A' from the following compounds :
(A) 1-Pentene (B) 2-Pentene
(C) 2-Methyl-2-pentene (D) 2-Methyl-1-pentene
24. Which of the following compounds can be detected by Molisch’s test :
(A) Nitro compounds (B) Sugars (C) Amines (D) Primary alcohols
25. Which branched chain isomer of the hydrocarbon with molecular mass 72u gives only one isomer
of mono substituted alkyl halide ?
(A) Tertiary butyl chloride (B) Neopentane
(C) Isohexane (D) Neohexane
26. Iodoform can be prepared from all except :
(A) Ethyl methyl ketone (B) Isopropyl alcohol
(C) 3–Methyl–2–butanone (D) Isobutyl alcohol

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ANSWER KEY
EXERCISE-1 (EXERCISE FOR JEE MAIN)
1. C 2. C 3. B 4. B 5. C 6. D 7. B
8. C 9. B 10. C 11. C 12. B 13. A 14. A
15. C 16. A 17. C 18. A 19. B 20. B 21. C
22. C 23. D 24. D 25. A 26. B 27. D 28. A
29. C 30. C 31. B 32. B 33. A 34. D 35. A
36. B 37. A 38. A 39. A 40. B 41. B 42. D
43. A 44. B 45. D 46. A 47. C 48. C 49. D
50. B 51. D 52. C 53. A 54. C 55. D 56. C
57. C 58. C 59. A 60. B 61. B 62. B 63. D
64. D 65. D 66. D 67. C 68. C 69. B 70. C
71. A 72. B 73. A 74. C 75. B 76. A 77. D
78. B 79. B 80. B 81. A 82. C 83. B 84. C
85. C 86. C 87. B 88. A 89. B 90. B 91. C
92. C 93. D 94. A 95. B 96. C 97. B 98. B
99. D 100. C 101. A 102. B 103. A 104. C 105. A
106. C 107. A 108. C 109. D 110. A 111. B 112. C
113. B 114. D 115. C 116. C 117. C 118. C 119. D
120. A 121. D 122. A 123. C 124. B 125. C 126. B
127. C 128. A 129. D 130. C 131. A 132. D 133. D
134. B 135. B 136. D 137. D 138 D 139 D 140. B
141. D 142. C 143. A 144 C 145 B 146. B 147. B
148. C 149 A 150 A 151. D 152. C 153. A 154. C
155. D 156. B 157. B 158. A 159. A 160. B 161. A
162. A 163. B 164. C 165. C 166. D 167. C 168. C
169 B 170. D 171. C 172. A 173. C 174. A 175. A
176. C 177. B 178. D 179. C 180. D 181. B 182. D
183. C 184. B 185. C 186. B 187. A 188. B 189. C
190. D 191. B 192. B 193 C 194. D 195. C 196. B
197. D 198. C 199. C 200. D 201. A 202. C 203. C
204. C 205. D 206. D 207. C 208. B 209. C
EXERCISE-2 (EXERCISE FOR JEE ADVANCED)
1. A 2. A 3. D 4. B 5. C 6. B 7. C
8. D 9. B 10. C 11. B 12. D 13. D 14. B
15. A 16. B 17. C 18. D 19. C 20. B 21. D
22. A 23. D 24. D 25. B 26. D 27. A 28. C
29. C 30. B 31. D 32. B 33. C 34. C 35. A
36. C 37. D 38. D 39. B 40. D 41. B 42. A
43. C 44. C 45. C 46. C 47. B 48. B 49. B
50. B 51. B 52. A 53. B
ONE OR MORE THAN ONE CHOICE CORRECT
1. (B,C,D) 2. (B,D) 3. (A,C,D) 4. (A,C) 5. (A,B,C,D)
6. (A,B,C,D) 7. (A,B,C) 8. (B,C) 9. (A,B,D) 10. (C,D)
11. (A,B) 12. (A,B,C) 13. (C,D) 14. (A,C,D) 15. (A,B,C)
16. (A,C,D) 17. (A,B,C,D) 18. (A,B,C) 19. (A,B,C,D)

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COMPREHENSION TYPE
1. (B) 2. (B) 3. (C) 4. (A) 5. (C)
6. (D) 7. (B) 8. (D)

MATCH THE COLUMN

1. A  s, B  r, C  q,D  p
2. A  q, B  p, C  s D r
3. (A - q ; (B) - s ; (C) - p ; (D) - r
4. (A) - p,q,t ; (B) - s ; (C) - r,t ; (D) - q,r,s.
5. (A) - p, s ; (B) - p, q ; (C) - q, r, s ; (D) - r

SUBJECTIVE TYPE
1. Monosaccharide is a carbohydrate that cannot be hydrolysed further to give simpler unit of polyhydroxy
aldehyde or ketone.

2. Those carbohydrates which reduce fehling’s solution and tollen’s reagents are called reducing sugars.

3. The oxide linkage between two monosaccharides, formed by loss of a water molecule is called
glycosidic linkage.

4. Glucose and fructose

5. Starch has (C1 – C4)  glycosidic linkage between  - D glucose units, cellulose has (C1 – C4) 
glycosidic linkage between -D glucose units

6. 3HNO
 

7. (i) Though glucose has aldehyde group, it does not give 2,4-DNP test
(ii) It does not form hydrogen sulphite addition product
(iii) The pentacetate of glucose does not react with hydroxyl amine.
Above facts indicate the absence of free – CHO group in glucose.

8. The spontaneous change in specific rotation of an optically active compound in solution with time, to
an equilibrium value, is called mutarotation

9. Glucose has five –OH group and sucrose has ten–OH group and because of hydrogen bonding with
H2O molecules glucose and sucrose are soluble in water.

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10. L- Fructose is enantiomer of D-Fructose.

11. Amino acids contain two functional groups which can make H-bonds that is the resaon why they
have high m.p.and soulbility in water .

12. (a) The amino acids which can be synthesised in the body - non-essential ex. Glycine, Alanine.
(b) The amino acids which cannot be synthesised and must be obtained through diet. ex. valine,
leucine.

13. Due to the presence of both acidic and basic groups in the same molecule. In aqueous solution –
COOH group can lose a proton and –NH2 group can accept a proton and forms zwitter ion. In zwitter
ionic form amino acids show amphoteric behaviour.

14. Due to its existence in the form of zwitter ion, there exist a very strong intermolecular attraction
which is responsible for high melting point of amino acid.

15. Number of amino groups is more than the number of carboxylic groups.

16. + 

+ 

17. (a) (b)

(c) (d)

18. 2° & 3° structres are lost on heating / treatment with acids or bases.

19. Buna-N  Copolymer of 1, 3 -butadiene and acrylnitride

Buna-S  Copolymer of 1, 3 -butadiene and styrene

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20. II < III < I

21. Addition polymer : polyvinyl chloride, polythene condensation polymer : Bakelite, terylene

22. Copolymerisation  in which a mixture of more than one monomeric species is allowed to polymerise
and form a copolymer.
Example (i) Buna- S (ii) Buna - N

Cl
|
23. CH2  C  CH  CH2
24. (i) Aldopentose (ii) Aldotetrose (iii) Ketopentose (iv) Ketohexose

25. Carbohydrate

Anomers : () ()

Epimers :

Enantiomers :

Ketose :

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26. 27. –anomer = 37.2%, –anomer =

62.8%

28. 9 29. (A) =

COOH CH2 – OH
| |
CH – OH CH – OH
| |
CH – OH CH – OH
| |
30. (A) CH – OH (B) CH – OH
| |
CH – OH CH – OH
| |
CH2 – OH CH2 – OH

31. (A) (B) (C)

32. (a) < 7 , (b) << 7 , (c) > 7


33. (a) H3 N– CH – COO – (b) H2N – CH – COONa
| |
CH2 – CH2 – COOH CH 2 – CH 2 – COOH

34. 6

O O
|| ||
35. (A) CH3 – CH – C – OH (B) CH3 – CH – C – OH (C) (D)
| |
NH2 OH

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36. decarboxyl ate (optically active)

  


(A.A)

37. (a) By NaHCO3 (By ninhydrin test)

 
(b) By Heating  –A–A  ,  –A–A  R–CH= CH–COOH
– 2H2O

–A–A 


38. 3

39. (a) Pro –Ser–Thr–Hyp (b) Leu–Ala –Cys–Arg–Val

40. Glutamic acid undergoes deprotionation as :

In order to supress the above ionization so that zwritter ion predominate, higher [H+] will have to be
maintaned and there for isoelectric pH will be lower. Glutamine is a monocarboxylic acid and hence
no extra H+ is released to supress above type of ionization and hence isoelectric pH is higher.
O
||
H O / heat
41. CH3  C  H  NH3  HCN  CH3  CH  CN 3  
H2O

|
NH2

42. (a) (b)

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43. (a) + CH2 = CH – CN (b) CH2 = CCl2 (c) +

44. (i) - Amino sugar (ii) - Glycosyl amine (iii) - Glycosyl amine

45. &

46. 32 – aldoheptoses 16 are D–sugars 16 are L–sugars

47. Schiff’s reagent and bisulphite cannot open the ring structure.

4HIO 4 HIO
48. -glucose    5HCOOH + HCHO ; -glucose    5HCOOH + HCHO
oxidation fast oxidation slow

Reason :

cis-1, 2-diol can form a cyclic ester with HIO4 so it is oxidized more rapidly than latter.

trans-1, 2-diol can’t form a cyclic ester initially. First the ring opens then only it can undergo oxidation.

49.  

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50. Due to formation of carbocation which is planer.

51. Due to the difference in configuration

Dotted system of both have same configuration, > C = 0 on reduction in fructose gives two different
configuration at C2*.
52. Glucose is reducing in nature due to the presence of open chain aldehydic form in equilibrium with
cyclic isomers.
Glycoside Cyclic acetal formed by reaction between glucose & CH3OH. It exist in two anomeric
forms ( & ). These are stable towards bases & are not hydrolyzed in fehling or Tollen’s reagent.
53. Reason
No free-CHO gp.
No hemiacetal linkage
Acylation of D-glucose does not give an open chain aldehyde.
54. Glucose & fructose
In aq. solution these sacc. containing hemiacetal or hemiketals exist in equill. with a small amount of
open chain aldehyde or -hydroxy ketonic form and when treated with reagents, open chain form
oxidize.
In Sucrose reducing part are not free and are involve in glycosidic linkage.

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tautomerises
55. Fructose      D – Glucose + D – mannose
Which are oxidised to corresponding acids which are not sweet more ever hemiacetal structures
under goes fission on heating to less carbon structures which are not sweet.

56. , NO

57. In hydrolysis of sucrose glucose is obtained as cyclic pyranose form responsible for mutarotation.
58. Glucose gives positive test with tollen’s reagent and fehling solution while Glycine does not give
these tests.
59. Glucose declourises red colour of Br2 water and oxidised to Gluconic acid.
Fructose does not react with Br2 water.
60. 61.

62. 63.

64. (A) (B) (C)

65. (A) CH3–CHO (B) CH3 – CH – COOH

|
NH2
 
66. (A) H2N – CH – CH2 – NH – CH2 – CH2OH (B) H3 N – CHCOOEt (C) H 3 N – CH 2 – COOEt
| |
CH3 CH3

O O CH3
|| || |
(D) HO – CH – C – NH – CH2 – C – OH (E) CH3 – C – NH – CH – C – NH – CH2
| || || |
CH3 O O COOH

(F) Ph – CH 2 – NH – CH – CONH – CH2 COOH

|
CH3

67. (A) (B) (C) (D)

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O O
|| ||
68. (A) CH3 – CH – C – NH2 (B) CH3 – CH – C – OH (C) (D)
| |
NH OH
2

69. (A) CH 2  CH – CH 2Br (B) CH2  CH – CH2 CN

O
||
(C) CH2  CH – CH2 – C – OH (D) CH2  CH – CH – C – OH
|| |
O
Br

O O
||
|| HN R
(E) CH2  CH – CH – C – OH (F) NH
(R = – CH = CH2 )
| R
||
NH 2 O

70. (A) (B)

71. (A) (B) (C)

72. (A) (B) (C)

(R, S mixture) (S–amino acid) (R–amino acid)

73. (A) (B)

(C) (D) H2N – CH  COOH (E) H2N – CH – COOH

| |
( CH2 ) 3 – OH (CH2 )3 Cl

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74. + H2N – CH – COOH

|
CH3

75. (a) CH3  CH  COOH

|
NH2 ( Alanine )

Structure of alanine at pH  2
PH = 2 (Basic group is ionised) CH3  CH  COOH
|

NH3

Structure of alanine pH  10
PH = 10 (Acidic group is ionised) CH 3  CH  COO ¯
|

NH 3

3Br
(b) 2
   + CHBr3
4NaOH Bromo form
( 3NaBr
3H2O ) Compound ' A'

76. (i) Sucrose  A + B

‘A’ is D(+) - Glucose
‘B’ is -D(-) - Fructose

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Structure of ' B'

Structure of ' A ' CH2 OH
CHO |
| CO
H  C  OH |
|
HO  C  H
HO  C  H
|
|
H  C  OH H  C  OH or
| |
H  C  OH H  C  OH
| |
CH2 OH CH2OH
D( )  glu cos e D( ) Fructose

O

||
(ii) H Polymerisa tion [ ..... NH ( CH .....]n
      2 5 C
) 
Nylon  6  (Perlon)

77. 3 78. 6 79. 3

CH3 CH3 CH3
| | |
80. (i) CH3  C  C – CH3 (ii) CH3  CH  CH2  CH3 81. 2 82. 5
|
CH3

83. Only one alkene

Three monochloro isomers are possible as it has three different types of 'H' atoms.

84.

85. , 86.

87. 2 88. 2 mole 89. 90. 4

91. 92. (1), (3), (4), (6), (7), (8) (9) (10).

93. Possible structures of Q & R will be Acetone and propanal, because these are isomers of carbonyl
compounds.
The other compounds (S) can be propandial or 2-oxopropanal.

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94. No. of active H = 2

95. 10 96. (i) 3 (ii) 4 (iii) 5 (iv) 3 97. 2

98. P ; Q ; R

X  4 monochloro structural products

3 O
99. (X) 

Zn, H2O

Cl , h
(Z) 2 2 Products

100.

H2 Cl ,h
101  (CH3)3C–CH2–CH2–C(CH3)3 (P) 2
(M)   2 products

(CH3)3C–CHO (W)

102. 5

103. 3º alcohol gives instant turbidity with lucas reagent.

104. (A) is CH2Cl.C  CH, i.e., 3-Chloropropyne

105. A=

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EXERCISE-3 (IIT JEE PREVIOUS YEAR'S QUESTIONS)

CH2  C 6H5
|
1. H2N  CH  CONH  CH  COOCH3
|
CH2  COOH
Aspartame ( Asparta min e )

(i) In aspartame four functional groups are present which are

(a) – NH2 (Amine) (b) (– COOH) (Carboxylic acid)
O O
|| ||
(c)  C  NH  (2 amide) (d)  C  O  (Ester )

CH2C6H5
 |
(ii) Zwitter ion structure is givens as below : H2N  CH  CONH  CH  COOCH3
|
CH2  COO ¯

O CH2C 6H5
|| | H2N  CH  COOH CH2C 6H5
Hydrolysis
(iii) H2N  CH  C  NH  CH  COOCH3    | + |
| CH2COOH H2N  CH  COOH
CH2COOH
( a) (b )
Hence on hydrolysis two amino and (a) and (b) are obtained.
(iv) In above to amino acids NH2  CH  COOH is more hydrophobic due to presence of non-polar
|
CH2  H5 C 6
C6H5–CH2– or benzyl group.

2. Peptide linkage is and it is formed by the condensation between — NH2 group and —
COOH group as follows

(CH3 )2 CHCH2CHCOOH + H2NCOCH2CH2  CHCOOH 

| |
NH2 NH2

+ (CH3 )2 CHCH2CHCO  NHCHCOOH

| |
NH2 CH2 CH2CONH2

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3. Ziegler Natta catalyst. (R3Al + TiCl4)
4. (B)

5.

6. (B)
7. P is a reducing sugar as one monosaccharide has free reducing group because glycosidic linkage
is (1, 4). Whereas in Q both the reducing groups are involved in glycosidic bond formation
8. (A - p, s); (B - q, r); (C - p, r); (D - s) 9. (C) 10. (A) 11. (D)
12. (B,C) 13. 6 14. (B) 15. (C,D) 16. 8
17. 4 18. 6 19. 4

20. (A) (B) (C) (D) 21. (C)

(JEE MAIN PREVIOUS YEAR'S QUESTIONS)

1. (3) 2. (2) 3. (3) 4. (3) 5. (3)
6. (3) 7. (2) 8. (3) 9. (4) 10. (3)
11. (2) 12. (3) 13. (2) 14. (2) 15. (1)
16. (D) 17. (A) 18. (B) 19. (D) 20. (D)
21. (D) 22. (A,C) 23. (C) 24. (B) 25. (B)
26. (D)

127 CLASS XII CHEMISTRY