ANSWER SCHEME TUTORIAL SK025 SEMESTER 2

SK025
CHAPTER 4.0: INTRODUCTION TO ORGANIC CHEMISTRY

CHAPTER 4.0 :INTRODUCTION TO UNIT4.1 : MOLECULAR AND

ORGANIC CHEMISTRY STRUCTURAL FORMULA
LEARNING OUTCOMES:
a) Define structural formula
b) Draw structural formula in the form of expanded, condensed and skeletal structures based on molecular formula
c) Classify carbons into primary, secondary, tertiary or quaternary and hydrogens into primary, secondary or tertiary.

TUTORIAL QUESTIONS :

1. (a) Define the term structural formula.

(b) Draw the expanded structure for each of the compounds:
i. CH3CH2CH3 ii. CH3CH(Cl)CH2COOH

(c) Draw the condensed structure for each of the compounds:

i. ii. O
OH

iii. iv. OH

Cl O

(d) Draw the skeletal structure for each compound given below:
CH3 CH3
i.
CH3CH CH2CH2CHCH2CH3 Br
CH3CH2CHCH2C OH
ii. (CH3)3CCH2CH2CH2OH iv. O

iii. v. CH3CH(Cl)CH2COOH
HC CH2

HC CH2
ANS:

1 (a) Structural formula is a chemical formula which shows how the atoms in a molecule are
bonded to each other
(b) i. H H H ii. H H H O

H C C C H H C C C C O H

H H H H Cl H

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CHAPTER 4.0: INTRODUCTION TO ORGANIC CHEMISTRY

(c) i. CH3CH(CH3)CH2OH ii. CH 3CH 2CH(CH 3)CCH(CH 3)2

o

iii. iv. CH3CH(Cl)CH2COOH

HC CH2

HC CH2

OH
(d) i. iv.

O Br O

ii. v.
OH OH

Cl O

iii.

2. (a) Identify classes of carbons in this structure;

CH3
CH3CHCH2CH2CCH3
CH3 CH3

ANS:

10
0
10 3 20 20 CH3
CH3CHCH2CH2CCH310
CH3 40 CH3
10 10

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CHAPTER 4.0: INTRODUCTION TO ORGANIC CHEMISTRY

CHAPTER 4.0 :INTRODUCTION TO UNIT 4.2: FUNCTIONAL GROUPS &

ORGANIC CHEMISTRY HOMOLOGOUS SERIES
LEARNING OUTCOMES:
(a) Define functional groups
(b) State functional group and identify functional groups in a given compound.
(c) Identify functional groups in a given compound.
(d) Define homologous series.
(e) Explain general characteristics of homologous series: represent by general formula, same functional groups and chemical
properties, gradual change in physical properties with increasing and successive member of a series by a –CH2- group.

TUTORIAL QUESTIONS :

1. (a) Explain the terms functional group and homologous series.

(b) Draw the structural formula for ;

i. an aldehyde (C5H10O) ii. a ketone (C4H8O)

iii. a carboxylic acid (C3H6O2) iv. an amine (C5H13N)

v. an amide (C2H5NO) vi. an alcohol (C2H6O)

vii. an ester (C3H6O2) viii. an ether (C2H6O)

ANS :

(a) Functional group is an atom or group of atoms in an organic molecule which

characterized the molecule and enables the molecule to react in specific ways
(determine its chemical properties).

(b) Homologous series is a series of compounds where each member differs from the
next member by a –CH2– group.

i. O ii. O
CH3CH2CH2CH2CH CH3CH2CCH3
iii. O iv. CH3CH2CH2CH2CH2NH2

CH 3CH2COH
v. O vi. CH3CH2OH
CH3CNH2
vii. O viii. CH3 OCH3

CH3COCH3

* other possible isomers

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CHAPTER 4.0: INTRODUCTION TO ORGANIC CHEMISTRY
2. Identify and name the functional groups present in the following molecules:

(a) CH2OH

NHCH3
(b) CH2OCH3

NHCOCH3
(c) O Cl
COOH
C C H
C
O
C O
O
ANS :
a)
CH2 OH
hydroxyl

NH CH3
benzene ring amino
b)
CH2OCH3

alkoxy
NHCOCH3

benzene ring carboxamide

c)

benzene ring halogen

carbonyl O Cl
COOH carboxyl
C C H
C
O
C O carbonyl
carbon-carbon double bond
O
carbon-carbon triple bond
carboalkoxyl

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CHAPTER 4.0: INTRODUCTION TO ORGANIC CHEMISTRY

CHAPTER 4.0 :INTRODUCTION TO UNIT4.3: ISOMERISM

ORGANIC CHEMISTRY
LEARNING OUTCOMES:
a) Define isomerism constitutional isomerism and stereoisomersm
b) Identify and construct constitutional isomerism (chain/positional/functional group isomers)
c) Describe cis-trans isomerism due to restricted rotation about C=C bond and C-C bond in cyclic compound
d) Identify cis trans isomerism of a given structural formula
e) Define chirality centre and enantiomers
f) Identify chirality centre in a molecule
g) Determine optical activity of compound
h) Draw a pair of enantiomers using 3D formula restricted to molecules with one chirality centre.

TUTORIAL QUESTIONS :

1. (a) Define the term isomer.

(b) Draw all posibble isomers of compound with the molecular formula C 4H10O and
identify the types of isomerism present.

ANS:

(a) Isomer is the existence of different compounds with the same molecular formula.

(b)
CH3CH2CH2CH2OH ii. CH3CH2CHCH3
i.
OH
iii. CH3 iv. CH3CHCH2OH

CH3CCH3 CH3

OH
v. CH3CH2CH2 O CH3 vi. CH3CH2 O CH2 CH3
vii. CH3CH O CH3
CH3

Positional Isomerism: i and ii, v and vi (different position FG in same skeletal)

Chain Isomerism: i and iv , ii and iii (different branch)
Functional Group Isomerism: i and v (different FG)

2. For each of the following compounds, draw its isomeric pair that represents a chain,
positional and functional group isomerism:
(a) CH3CH2CH=CH2
(b) CH3CH(CH3)CH(CH3)CH3
(c) CH3CH2CH2CH2CH2OH

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CHAPTER 4.0: INTRODUCTION TO ORGANIC CHEMISTRY
ANS:

(a) CH3CH2CH=CH2 and CH3CH=CHCH3 Positional

isomers
CH3CH2CH=CH2 and CH3CH(CH3)=CH2 Chain isomers
CH3CH2CH=CH2 and Functional
group isomers

(b) CH3CH2(CH3)CH2(CH3)CH3 and CH3CH2(CH3)CH2CH2CH3 Chain isomers

(c ) CH3CH2CH2CH2CH2OH and CH3CH(CH3)CH2CH2OH

Chain isomers
CH3 CH2 CH2 CH2 CH2 OH CH3CH2CH2OCH2CH3
and Functional
group isomers
CH3 CH2 CH2 CH2 CH2 OH and CH3CH(OH)CH2CH2CH3 Positional
(a) What are the essential requirements for a molecule to exhibit cis-trans isomerism?
isomers
(
3 a) What are the essential requirements for a molecule to exhibit cis-trans isomerism?
b) Which of the following compounds can exist as a pair of cis-trans isomers? Draw
the cis-trans isomers.
i. ClCH=CHCl ii. BrCH=CHCl
iii. CH3CH=CH2 iv. (CH3)2C=CHCH3
v. CH3CH2CH=CHCH3 vi. (CH3)2C=C(CH3)CH2CH3
vii.
Br Br
ANS:
(a) i. Restricted rotation about a C = C double bond in alkenes or a C – C single
bond in cyclic compounds.
ii. Each carbon atom of a site of restricted rotation has two different groups attached
to it.
(b) iii, iv and vi : none
v. CH3CH2 CH3 CH CH 3 2 H
C=C C=C
H H H CH3

cis-2-pentene trans-2-pentene
i. H H H Cl

C=C C=C

Cl Cl Cl H
cis-1,2-dichloroethene trans-1,2-dichloroethene
ii. H H H Cl

C=C C=C
Br Cl Br H
cis-1-bromo-2-chloroethene trans-1-bromo-2-chloroethene
Br Br Br H
vii.

H H H Br

cis-1,4-dibromocyclohexane trans-1,4-dibromocyclohexane

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CHAPTER 4.0: INTRODUCTION TO ORGANIC CHEMISTRY
4. Draw all the structural formulae of alkenes C5H10. Identify the structure that exhibits cis-
trans isomerism.

ANS:
i. CH3CH2CH2CH=CH2 ii. CH3CH2CH=CHCH3
iii. CH3CH2C=CH2 iv. CH3CH=CCH3 v. 3-methyl-1-butene
CH3 CH3
2-pentene has cis-trans isomers:-
CH3 CH2 CH3 H3C H
C C C C
H H H CH2 CH3
cis-2-pentene trans-2-pentene

5. Draw and label the cis-trans isomers of 1,2-dichloroethene.

ANS:
H H H Cl
C C C C
Cl Cl Cl H
cis-1,2-dichloroethene trans-1,2-dichloroethane

6. (a) What is meant by chirality centre?

(b) From the following list, identify the compounds that exhibit optical activity:
i. CH3CH=C(CH3)CH2CH3 ii. CH3CH(OH)CH2CH3
iii. CH3CH2CH(Br)CH2CH3 iv. CH3CH(NH2)COOH

ANS:
(a) Chirality centre: a sp3-hibridized carbon atom with 4 different groups attached to it.
(b) ii and iv

7. (a) State the structural features of a molecule in order to be optically active.

(b) Draw the structural formula of 2-bromobutane and indicate the chiral carbon
using an asterisk (*).
(c) Use a three-dimensional formula to show the structural formulae of enantiomers in
(b).

Answer:

(a) i. Molecule contains a chiral carbon or chiral centre (chirality center - an

sp3 hibridised carbon atom with 4 different groups attached to it)
ii. The molecule and its mirror image are not superimpossable.
(b) *
CH3CH(Br)CH2CH3
CH 2CH 3 CH2CH3
(c)
C C
H3C CH3
H Br Br
H
Enantiomers

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CHAPTER 4.0: INTRODUCTION TO ORGANIC CHEMISTRY
CHAPTER 4.0 : INTRODUCTION TO UNIT4.4 : REACTIONS IN ORGANIC
ORGANIC CHEMISTRY COMPOUNDS
LEARNING OUTCOMES:
a) Explain covalent bond cleavage (homolytic/heterolytic)
b) Differentiate homolytic and heterolytic cleavage
c) State relative stabilities of primary, secondary and tertiary free radicals, carbocations and carbanions.
d) Compare the stabilities of carbocations and carbanions by using the inductive effect of alkyl group.
e) Define electrophile and nucleophile, Lewis acid and Lewis base.
f) State main types of organic reactions (addition/substitution/elimination/rearrangement)
g) Identify the main type of organic reaction given a reaction equation.

TUTORIAL QUESTIONS :

1. Explain the differences between homolytic cleavage and heterolytic cleavage. Give one
example for each cleavage.

ANS:

Homolytic Cleavage Heterolytic cleavage

 occurs to in non-polar bond  occur to in polar bond

involving two atoms of similar involving unequal sharing of
electronegativity. electron pair between two
atoms of different
electronegativities.

 A single bond breaks  A single bond breaks

symmetrically into two equal unsymmetrically and both
parts, leaving each atom with the bonding electrons are
one unpaired electron. transferred to the more
electronegative atom.

 Forms free radicals.  Forms cation and anion.

Eg: ClCl 2Cl∙ Eg: H3CCl  H3C+ + Cl

2. Arrange the following carbocations in order of increasing stability.

CH3 CH3 H
H3C C +CH2 H3C C CH2CH3 +CH H3C C CH2CH3
3
+ +
H
ANS:
H CH3 CH3
+CH
3 < H3C C CH2CH3 < H3C C CH2 < H3C C CH2CH3
+ + +
H

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CHAPTER 4.0: INTRODUCTION TO ORGANIC CHEMISTRY

3. (a) Define the terms electrophile and nucleophile.

(b) Classify each of the following as electrophile, nucleophile or free radical.

i. NH3 ii. Br iii. H2 O
iv. NO2+ v. NO2 vi. Cl+
vii. BF3 viii. CO2 ix. CH3CH=CH2
x. CH3OH xi. PCl5
ANS:

(a) Electrophile : a species that can accept an electron pair .

Nucleophile : an electron-rich species that can donate a pair of electrons to
form a bond.

(b) Nucleophile: i, v, ix, x Electrophile: iv, vi, vii, xi Free radical: ii

H2O & CO2 can be either electrophile & nucleophile

4. Chloromethane reacts with hydroxide ion to form methanol as shown in the equation
below.
OH + CH3Cl  CH3OH + Cl

(a) Identify the nucleophile and electrophile.

(b) State the type of reaction.

ANS:

(a) Electrophile : CH3Cl Nucleophile : OH-

(b) Nucleophilic substitution reaction

5. State the type of reactions:

(a) O O
C OH C Cl
SOCl2

(b) CH2=CH2 + HCl  CH3CH2Cl

(c) CH2=CH2 + H2O H2SO4 ,   CH3CH2OH
catalyst

(d) CH3CHBrCH3    CH2=CHCH3 + HBr

KOH, alcohol

(e) CH4 + Br2 

uv
CH3Br + HBr
(f) NO2
+ HNO3 H2SO 4

(g) Br H
CH3COOH
CH3CH CH CH3 + Zn CH3C CH CH3
Br

ANS:

(a) nucleophilic substitution (b) electrophilic addition

(c) electrophilic addition (d) elimination
(e) free radical substitution (f) electrophilic substitution
(g) elimination

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CHAPTER 4.0: INTRODUCTION TO ORGANIC CHEMISTRY

6. Based on the reaction scheme below, state the type of reaction corresponding to steps A, B
and C.

A
CH3 Br2 CH3
| uv |
CH3CHCH2CH3 CH3 CHCH2CH2Br

KOH/ethanol B

CH3 CH3
| HBr |
CH3C(Br)CH2CH3 CH3C=CH2CH3
C

ANS:

A = free radical substitution

B = elimination
C = electrophilic addition

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CHAPTER 4.0: INTRODUCTION TO ORGANIC CHEMISTRY

OBJECTIVE QUESTIONS:

1. The two types of stereoisomers are

A. diastereomers and enantiomers.

B. enantiomers and positional isomers.
C. chain isomers and positional isomers.
D. diastereomers and functional group isomers.

Explanation:
Because positional isomer, chain isomers and functional group isomers are
structural/constitutional isomers.

2. Which of the following is a chiral molecule?

A. CH2BrI
B. CH3CBr2Cl
C. (CH3)2CHCl
D. CH3CHBrCH2CH3

Explanation:
Because structure D (CH3CHBrCH2CH3 ) has 4 different groups attach to carbon atom.

3. Vinyl acetate is used to make poly(vinyl acetate), PVA, plastic. The structure of vinyl acetate is
shown.
H H O
H C C O C CH3
Based on the given structural formula, vinyl acetate

A. is a cis isomer.
B. is a trans isomer.
C. exhibits structural isomers.
D. contains a chiral carbon atom.

Explanation:

The answer is not A and B because there is two hydrogen atom bondded to the same
carbon-carbon double bond. The answer is not B because there is no chirality center.
The answer is C because the structural isomer for vinyl acetate is
H H O H CH3 O
H3C C C O C H H C C O C H
,

4. The functional groups present in the amino acid with the structural formula as shown below are

HO CH2CHCOOH
NH2
A. alkoxy, carboxy, amide and benzene ring.
B. alkoxy, carboxyl, amino and benzene ring.
C. hydroxyl, carboxyl , amino and benzene ring.
D. hydroxyl, carbonyl, amino and benzene ring.

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CHAPTER 4.0: INTRODUCTION TO ORGANIC CHEMISTRY
Explanation
HO CH2CHCOOH carboxyl
NH2
hydroxyl
aromatic ring amino
5. The number of possible structural isomers for bromobutane, C4H9Br is

A. 2 B. 3 C. 4 D. 5

Explanation:
Possible structural isomers:
i) H iii) H H
H C CH2 CH2 CH3 H C C CH3
Br Br CH3
1-bromobutane 1-bromo-2-methylpropane
Br
H
ii) H C C CH CH iv) H3C C CH3
3 2 3
CH3
Br
2-bromobutane 2-bromo-2-methylpropane

6. Which of the following species is NOT an electrophile?

A. NH3 B. Br2 C. HBr D. AlCl3

Explanation:

Electrophile is an electron-deficient species which is capable of accepting electron pair(s). NH3

is a species that have lone pair in it. It means that NH3 is not an electrophile but nucleophile. In
other words, it is a Lewis acid.

7. Which of the following free radical is the most stable?

A CH3
B CH3CH2
C (CH3)2 CH
D
CH3

Explanation:
Because it is 3ο free radical

8. Which of the following species is nucleophile?

A. OH
B H+
C NO2+
D CH3+
Answer: A

Explanation:
Because it is electron-rich species
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CHAPTER 4.0: INTRODUCTION TO ORGANIC CHEMISTRY
9. Which of the following compound(s) is optically active?

A (Cl)CH2CH2CH3
B CH3CH(OH)CH2CH3
C CH3CH2COOH
D CH3CH(Cl)CH3

Answer : B

Explanation:
Structure B have chirality centre which is a sp3-hibridized carbon atom with 4 different groups
attached to it.

10. A pair of enantiomers has the following characteristic:

A They are non-mirror images.

B They are stereoisomers.
C Each enantiomer cannot rotates plane-polarised light in opposite direction of the other.
D They have restricted rotation in carbon-carbon double bond.
Answer : B

Explanation:
Enantiomers is a molecule that’s contains a chiral carbon or chiral centre (chirality center - an
sp3 hibridised carbon atom with 4 different groups attached to it) Its have mirror image that are
not superimposable (one of the stereoisomers)

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