Exercise 11

1. Identify the functional groups present in the following molecules and classify them into
homologous series.
a) CH3COOCH3
b) CH3CH2NH2
c) CH3CH2OCH2CH3
d) CH3CH2CH2CN
e) CH3CONH2
(5 marks)

2. a) Illustrate the expanded structural formulas for the following compounds.

i)
HO CN

ii) NH2

COOH
iii) CH3CH2CH2CH(Br)CH2CH2CHO

b) Illustrate the skeletal structural formulas for the following compounds.

i) (CH3)2CHCH2CH2CHCHCH2CH3

ii) H H H H Cl O H
H C C C C C C O C H
H H H H H H

iii) H
H
C N
C H
C C
H
H

c) Illustrate the condensed structural formulas for the following compounds.

i)

OH
 ii)
H H H H H H H
H C C C C C O C C H
H H H H H
(8 marks)

3. a) Give the structural formulas of the species formed from the homolytic cleavage of
tert-butyl hydroperoxide

CH3
CH3 C O O H
CH3

b) Give the structural formulas of the species formed from the heterolytic cleavage of
tert-butyl alcohol.

CH3
CH3 C OH
CH3

(4 marks)

4. Indicate the nucleophile and electrophile in the following reaction.

a)
H CH3 H CH3
C C + H Br H C C Br
H H H H

b)

c) O O
+ NH3 + HCl
CH3 C Cl CH3 C NH2

d)

(5 marks)
 5. Find the structural formulas for all the constitutional isomers of the alkene with the
molecular formula C6H12.
(12 marks)

6. An ester with the molecular formula C3H6O2 is a volatile compound and has a pleasant
odour.

a) Give two possible structural formulas for isomers of the ester compound.

b) Other than an ester, the molecular formula C3H6O2 also has one isomer with a different
functional group. Illustrate the isomer.
(3 marks)

7. Indicate the type of stereoisomerism for each of the following compounds and draw their
respective isomers. Identify the chiral carbon and mark it with an asterisk (*), if any.

a) (CH3)(CH3CH2)C=CH(CH2CH2CH3)
b) NH2CH(CH3)COOH
(6 marks)

8. Explain why the following compound has four stereoisomers.

CH3CH2CHCH2CH CHCH3
Br

(2 marks)
Exercise 12

1. a) Give the structural formula of the following molecule.

i) 1-isobutyl-3,3-dimethylcyclohexane

ii) 1-sec-butyl-3-isopropylcyclopentane

b) Write the IUPAC name for each compound.

i)

ii)

(4 marks)

2. An alkane contains five primary carbons, two secondary carbons, one tertiary carbon and
one quartenary carbon. Illustrate the possible structural formula of the alkane and write
the IUPAC name.
(2 marks)

3. Chloroethane can be produced when ethane is reacted with chlorine in the presence of
light.

a) Name the type of reaction.

b) Show the mechanism of the reaction

(4 marks)

4. a) Give the structural formula of the following molecules.

i) 2-methyl-3-ethyl-2-heptene
ii) 5-chloro-1,4dimethylcyclohexene
 b) Write the IUPAC name for each compound.

i)

ii)

(4 marks)

5. The reaction of 2-methylpropene with HBr produces a sole product, compound X.

CH3 H
C C + HBr X
CH3 H

a) Give the IUPAC name for the compound X.

b) The reaction proceeds through a two-step mechanism involving the formation of an

intermediate species. Give equations to illustrate the reaction mechanism.

(4 marks)

6. When 3-methyl-2-pentene is refluxed with a diluted acidic solution, it produces a mixture

of isomeric alcohol products.

a) Give the structural formulas of the products formed and identify the major and minor
products.

b) Identify the types of structural isomers for the products formed from the above reaction.

c) Give the mechanism for the reaction described above.

(11 marks)
7. Answer the following questions based on the following compound.
H CH3
C C
CH3CH2CH2 CH3

a) Give the IUPAC name for the above compound.

b) The compound undergoes oxidation when treated with hot acidified KMnO4 and forms
two products. Find the structural formulas of the products formed.

(3 marks)

8. An alkene Q undergoes oxidation reaction with potassium permanganate (VII) solution

under two conditions as shown in the scheme below. Indicate the position of the double
bond in Q and draw the structural formula for R.

OH
MnO4-/OH- MnO4-/H+ O
R Q +
cold heat O
(2 marks)
Exercise 13

1. Four isomers with a molecular formula of C4H9Br have different classifications of alkyl
halides. Find all isomers and classify them as primary, secondary or tertiary and give
IUPAC name for each isomer.
(12 marks)

2. Label β carbons in each alkyl halide and draw all possible elimination products formed
when each alkyl halide is treated with CH3CH2OꟷK+ in ethanol. Give major and minor
elimination products formed.

a) CH3CHClCH2CH(CH3)2

b) I

(12 marks)

3. Aqueous sodium hydroxide is heated with 1-bromopropane under reflux to produce an

alcohol.

a) Name the type of reaction mechanism for the above reaction.

b) Show the reaction mechanism for the above reaction.

c) Give the IUPAC name of the alcohol produced.

(5 marks)

4. Answer the questions based on the reaction sequence given below.

Reagent M NaCN
CH3CH2CH2MgBr CH3CH2CH2Br Q
O
1.
C
CH3 H
in dry ether
2. H3O+

conc. H2SO4
R S
(major)

a) Find the structural formula for compound Q and R.

b) Name reagents M and state the condition(s).

c) Name and give the structural formula for the geometrical isomers of compound S.
 d) State the rule that governs the formation of the major product of compound S.

e) Name the type of reaction and show the mechanism that leads to the formation of
compound Q.
(11 marks)

5. Consider the reaction scheme below.

a) Show the mechanism for the reaction when 3-bromo-3-methylpentane is refluxed with
water.

b) Give the structural formula of Y and explain the role of Y.

(5 marks)

6. a) Give IUPAC name of the following alcohols and classify them as primary, secondary or
tertiary.

i)

ii)

b) Find the structural formula for the major elimination product when each alcohol
undergoes acid-catalyzed dehydration.
i) 2-methyl-3-pentanol
ii) 1,2-dimethylcyclopentanol
(6 marks)
7. a) 2-Methyl-2-butanol reacts readily with HCl at room temperature to produce 2-methyl-2
chlorobutane.

i) Indicate the reaction type and specify the mechanism involved.

ii) Explain why this alcohol readily converts to an alkyl halide under those conditions.

b) When 2,2-dimethylpropanol reacts with thionyl chloride (SOCl2), white steamy fumes
are liberated.

i) Indicate the white steamy fumes.

ii) Give the structure of the product formed and state the mechanism involved.
iii) Explain why we do not treat 2,2-dimethylpropanol with HCl?
(10 marks)

8. Alcohols with the molecular formula of C4H10O have four isomers.

a) Give all structural isomers and arrange them in order of ease of dehydration with acid.

b) Compare and contrast the behaviour of these alcohols when they are treated with

i) acidified potassium manganate (VII).

ii) alkaline iodine in aqueous potassium hydroxide.
iii) ZnCl2 in concentrated HCl.
(12 marks)
Exercise 14

1 Illustrate the structural formulas of the following compounds.

a) 2-Chloro-3-methylpentanal
b) 4-Bromo-3-methylbutanal
c) 3-Methyl-2-pentanone
d) 4,4-Dimethylcycloheptanone
(4 marks)

2. a) Illustrate and name all possible isomers of carbonyl compounds with the molecular
formula C5H10O.

b) Based on the structures you have drawn in (a), choose:

i) the compound(s) that can be oxidised with hot KMnO4/H+.

ii) the compound(s) that give(s) positive results with Fehling’s solution and Tollen’s
reagent.

iii) the compound(s) that give(s) yellow precipitate with iodine in alkaline solution
(iodoform test).

iv) the compound(s) that has stereocenter(s).

(12 marks)

3. Show schematically to carry out the following conversions.

a) Bromopropane to propanone.
b) Propanone to 2-methyl-2-butanol.
c) Butene to 2-butanone.
(8 marks)

4. Both organic compounds X and Y have a straight-chain structural formula containing six
carbons and one oxygen. However, compound X has two more hydrogens than
compound Y. Several experiments were set up to investigate the presence of functional
groups and the structure of both compounds. The following tests and results are shown
below.

Chemical test Compound X Compound Y

Iodoform test Yellow precipitate No precipitate formed

Brady’s reagent No precipitate formed Yellow or orange precipitate

Lucas reagent Cloudy solution in a few minutes No cloudiness

Hot KmnO4/H+ Purple solution decolourised Purple solution decolourised

 Predict the structure of compounds X and Y based on the following tests given.
(10 marks)

5. Name the following carboxylic acid and its derivatives according to IUPAC nomenclature.

a)
CH2CH3
CH3CH2CH2 C CH2COOH
H

b) O

Br OH

c) O

d) CH3 H O CH3
CH3CHCH2 C C O C CH2CH3
CH3 H
(4 marks)

6. Show schematically how to carry out the following conversions.

a) 2-methylpropanoic acid to 2-methylpropene

b) chloropropane to propanoic acid.
c) ethanol to ethanamide.
(11 marks)
7. Consider the reaction scheme below.

CH3MgBr
1. dry ether Reagent A Alcohol W
X Y CH3COOH CH3COOCH2CH3
2. H3O+ conc. H2SO4/
heat
Reagent B

CH3COCl
NH3

a) Give the structural formulas for X, Y and Z.

b) Name the reagent(s) and state the condition(s) for A and B.

c) Give the structural formula for alcohol W.

(6 marks)

8. a) Give and name all possible structures of esters with the molecular formula C4H8O2.

b) Based on the structures you have drawn in (a), choose the

i) isomer(s) that produce(s) ethanoic acid during acid hydrolysis.

ii) isomer(s) that produce(s) primary alcohol during acid hydrolysis.
iii) isomer(s) that produce(s) secondary alcohol during acid hydrolysis.
iv) isomer(s) that produce(s) the methanol during acid hydrolysis.
(13 marks)