PRACTICE MODUL SK025 2nd Edition

PRACTICE MODULE CHAPTER 5 SK 025
5. 6-ethyl-2,5-dimethyl-4-propylnonane –

6. Octane =
7. 2,3-dimethylbutane =
8. 3,3-dimethylhexane =
9. 3-ethyl-3-

methylhexane =
10. 5,5-diethyl-2,2,4,4-tetramethyloctane =

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WORKSHEET 5.1 (a), (b) & (c) PRACTICE MODULE CHAPTER 5 SK 025
c.
1. Give the IUPAC name for each

compound

a. CH CH CH
CH 32 CH—3 CH 3
3

— CH—

b.
d.

e.

f.

2. Name the following alkanes according to the IUPAC rules:
(a) (CH3)2CHCH2CH2CH3 - _______________________________________
(b) CH3CH2C(CH3)2CH2CH3 - _____________________________________
(c) (CH3CH2)2C(CH3)CH2CH3 – ____________________________________
(d) CH3CH2CH(CH3)CH(CH3)CH(CH3)2 – ____________________________
(e) (CH3)3CCH2C(CH3)3 - ________________________________________

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PRACTICE MODULE CHAPTER 5 SK 025
(f) (CH3)2CHCH2CH2CH(CH2CH3)2 - _______________________________
(g) (CH3)2CHCH(CH3)CH2C(CH2CH3)2CH3 -__________________________
(h) (CH3)2CHC(CH2CH3)2CH2CH2CH3 – _____________________________
5.1 (d) SOURCES, PHYSICAL AND CHEMICAL PROPERTIES OF ALKANE
WORKSHEET 5.1 (d)(i)
1. Explain how the boiling points of alkanes increase with increasing relative molecular
mass

2. Explain how alkane with similar molecular mass, the boiling points will be lower for
branched alkanes as compared to straight chain alkanes.

WORKSHEET 5.1 (c)
1. In each pair of compounds, which compounds has the higher boiling point? Explain your
answer.
(a) Octane or 2,2,3–trimethylpentane

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PRACTICE MODULE CHAPTER 5 SK 025

(b) Heptane or 2–methylnonane

(c) 2,2,5–trimethylhexane or nonane

(d) butane & cyclobutene

2. Arrange the following hydrocarbons in order of decreasing boiling points: Explain your
answer.

3,3–dimethylpentane 2–methylheptane
2–methylhexane heptane

pentane

Answer :

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PRACTICE MODULE CHAPTER 5 SK 025

3. Arrange the following alkanes in increasing order of boiling point. Explain your answer.
Hexane, 2-methylpentane, 2,2-dimethylbutane, 2- methylhexane

Answer :

WORKSHEET 5.1 (d)(ii)
1. Rank the following compounds in order of increasing water solubility.
(CH3)3CH , CH3OCH2CH3 , CH3CH2CH2CH3 , CH3CH2CH2OH
Answer :

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PRACTICE MODULE CHAPTER 5 SK 025

2. Which compounds are water soluble?

CH CH OCH CH OH CH3CH2CH2CH2CH3 (CH3CH2CH2CH2)3
32 23

Answer :

3. Why are propane insoluble in water and soluble in organic solvent?

WORKSHEET 5.1 (e)

1. Complete the following equation for the combustion of alkane in limited oxygen.

(a) CH CH CH + O flame

323 2

(b) flame

+O 2

2. Complete the following equation for the combustion of alkane in excess oxygen

(a) CH3CH2CH2CH2CH(CH3)2 + O flame

2

(b) flame

7CO2 +
8H2O

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PRACTICE MODULE CHAPTER 5 SK 025

WORKSHEET 5.1 (f), (g) & (h)

1. Each of the following alkanes reacts with chlorine to give a single monochloro product on

the basis of this information, give the product formed.

a. CH4 + Cl2 uv

7CO2 +uv
b. CH3CH3 + Cl28H2O

7CO2 +
c. + Cl28H2Ouv

4. The chlorination of propane7uCnOd2er +sunlight forms compound X and Y.
a) Give structure X and8YH.2O
b) Write the mechanism for the formation of major product.

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PRACTICE MODULE CHAPTER 5 SK 025

WORKSHEET 5.1: ALKANE

MULTIPLE CHOICE QUESTIONS

Answer ALL the questions

1. What is the general formula for saturated hydrocarbons?
1. The reaction of cyclohexane with chlorine in the presence of light is a/an
A electrophilic addition
B electrophilic substitution
C free radical substitution
D free radical addition

2. Which of the following can behave as a free radical ?
A chloride ion
B chlorine atom
C chlorine molecule
D perchlorite ion

3. Name the following alkane :

CH3 CH3

H3C CH HC CH2 CH2 C CH3

H3C CH3

A. 2,2,5,6-tetramethylheptane
B. 2,3,6,6-tetramethylheptane
C. 1,1,2,5,5-pentamethylhexane
D. 2,2,5,6,6- pentamethylhexane

4.

Name the following alkane;
A. 3-ethylhexane
B. 2-methyl-3-ethyl pentane
C. 3-ethyl-2-methylpentane
D. 3-ethyl-4-methyl pentane

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PRACTICE MODULE CHAPTER 5 SK 025

For the questions 4 and 5 ,follow this options

A B CD
I only I and II II and III I, II and III

5. Which of the following statements show(s) that chlorination of alkane occurs via a free
radical substitution mechanism ?
I Homolytic fission of chlorine atom occurs in the presence of sunlight
II Free radical Cl was formed in the reaction
III Free radicals are found at the end of reaction
Answer :

6. Pick the trues statement about alkane
I It reacts with polar molecules
II It undergoes free radical substitution
III Its C-H bonds are non polar covalent bonds
Answer :

7. Which of the following compounds has the highest boiling point ?
A ( CH3)2CHCH3
B CH3(CH2)2CH3
C CH3(CH2)3CH3
D (CH3)2CHCH2CH3

8. Why do alkanes not dissolve in water?
A. they are less dense than water
B. they are non-polar compounds
C. they have low melting points
D. they are chemically less reactive

9. What is the general formula for saturated hydrocarbons?
A. CnH2n
B. CnH2n+1
C. CnHn+1
D. CnH2n+2

10. The following is an example of incomplete combustion:
A. C3H8(g) + 5O2(g) --> 3CO2(g) + 4H2O(l)
B. C6H14(g) + O2(g) --> CO2(g) + H2O(l)
C. C3H8(g) + 7/2O2(g) --> 3CO(g) +4H2O(l)
D. C6H12O6(aq) + 6O2(g) --> 6H2O (l) + 6CO2(g)

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PRACTICE MODULE CHAPTER 5 SK 025

WORKSHEET 5.1

MODEL OF PSPM QUESTIONS

1. Bromoethane will formed when X react with bromine in dichloromethane only under the
sunlight. Based on the statement:

(i) Draw and give IUPAC name the structure of compound X.
(ii) Write the equation of the reaction
(iii) State the type of reaction.
(iv) Show the mechanism of propagation step for the reaction.

2. The structure of compounds I, II, and III are shown below.
Arrange these compounds in order of decreasing order of boiling point. Explain your answer.

[10 marks]

3. a. Name the following compounds according to IUPAC nomenclature :

CH3

H3C CH3
Cl
(1 mark)

Answer : 1-chloro-1-isopropyl-3-methylcyclopentane

b. Arrange the following compound in order of increasing boiling point. Explain your
answer.

pentane , 2,2-dimethylbutane , 2-methylbutane

c. Propane undergoes chlorination to form 2 monochlorination products.
i. Draw the structures of the products formed.

ii. Give the IUPAC name for the products formed.

2. a) The following names are all incorrect, but they represent the real structure. Name the
compound correctly.

i. 2-cyclohexylbutane

ii. 1,2,2-trimethylcyclopentane

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PRACTICE MODULE CHAPTER 5 SK 025

b) If 25 ml of hexane were added to 100 ml of water in a beaker, what would you expect
to happen? Explain.

c) Alkanes known as paraffin are saturated hydrocarbon.
i. Explain why alkane are generally unreactive
ii. State the natural source of alkane.

d) 1-methylcyclohexane can react with chlorine with the presence of ultraviolet to form 1-
chloro-1- methylcyclohexane.Write equation for initiation and propagation steps.

ii. Which step in free radical substitution mechanism require outside energy? Explain.

Prepared by : Mdm Noor Najihah
Checked by : Mdm Noor Asmahan

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PRACTICE MODULE CHAPTER 5 SK 025
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PRACTICE MODULE CHAPTER 5 SK025

CHAPTER 5.2 : ALKENES

conc H SO H2
2 4 Pt @ Ni @
Pd @ Pd-C
KOH,reetfhluaxnol CH3C CH2
CH3 Cl2 @ Br2
CH2Cl2

Cl2 @ Br2
H2O

HCl @ HBr

H2O, H+

KMnO4/ OH-, KMnO4/ H+, HBr
cold  ROOR

i) O3
ii) Zn, H2O

@ (CH3)2S

MIND MAP ALKENE

5.2 : (a) STRUCTURE AND NAMING OF ALKENES

WORKSHEET 5.2.1

(A) Give the IUPAC name for the given structure of alkenes:
1. H2C CHCH2CH2CH2CH2CH3 = __________________________

(CH3)2C C CH(CH3)2 = __________________________

2. CH2CH3

H CH3 = __________________________

C C
3. CH3
CH2CH3

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PRACTICE MODULE CHAPTER 5 SK025
= ___________________________

4. Cl

F = _________________________________

5. C(CH3) CH2 = __________________________________
= __________________________________
6. H3C

7.
(B) Draw the structural formulae for each of the following alkenes:

i. 4,5-dibromo-1-heptene
ii. trans-2-hexene

iii. 3-methylcyclopentene

iv. 1-isopropyl-4-
methylcyclohexene

5.2 BOILING POINT OF ISOMERIC ALKENES

WORKSHEET 5.2.b

Choose and CIRCLE which member of pairs has highest boiling point. State the REASON.

PAIRS OF ALKENES REASON

Ethene and propene

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PRACTICE MODULE CHAPTER 5 SK025

Propene and 2-metylpropene

Trans 2- butene and
Cis-2-butene

5.2 PREPARATION OF ALKENES

WORKSHEET 5.2.c, d, e, f

i. Predict the product(s) of the following dehydration of alcohols and dehydrohalogenation of
haloalkanes reaction equations.

ii. Label the MAJOR product.
iii. State the RULE used to predict the major product.

DEHYDRATION OF ALCOHOLS:

H3C CH CH3 conc. H2SO4
a). OH 

Rule:

CH3 conc. H3PO4
H3CCH2CCH3 
b). OH

CH3 conc. H2SO4 Rule:
H2CCH CH2CH3  Rule:

c) OH

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PRACTICE MODULE CHAPTER 5 SK025

conc. H3PO4

d) OH 

CH3 conc. H2SO4 Rule:
 Rule:
OH

e)

DEHYDROHALOGENATION OF HALOALKANES

H3C CH CH3 NaOH, ethanol
a). Br reflux

Rule:

Cl CH3CH2ONa, ethanol
b). reflux
c) Br
Rule:
d) Br
CH3ONa, CH3OH
reflux

Rule:

KOH, CH3CH2OH
reflux

Rule:

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CH3 PRACTICE MODULE CHAPTER 5 SK025
NaOH, CH3CH2OH
Br
reflux
e)
Rule:

WORKSHEET 5.2. d
Propose the mechanism (MAJOR PRODUCT) for the following reaction:
Refer to the DEHYDRATION OF ALCOHOL questions (Worksheet 5.2 c, d, e, f):
ANSWER:

H3CCH CH3 conc. H2SO4 H3CCH +CH2 H2O

a) OH

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PRACTICE MODULE CHAPTER 5 SK025

ANSWER :

CH3 CH3

H3CCH2CCH3 conc. H3PO4 H3CCH + +C(CH3)2 H2O
 H3CCH2C CH2
OH
b) Major

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PRACTICE MODULE CHAPTER 5 SK025

ANSWER:

CH3 conc. H2SO4 CH3 CH3

+ +c)
H2C CH CH2CH3  H3C C CH CH3 H2C CCH2CH3 H2O
OH

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PRACTICE MODULE CHAPTER 5 SK025

d)

conc. H3PO4 + H2O

OH 

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PRACTICE MODULE CHAPTER 5 SK025

e) CH3 CH2
CH3
+ H2O
OH conc. H2SO4 +


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PRACTICE MODULE CHAPTER 5 SK025

WORKSHEET 5.2. g, h, j

ADDITION REACTION scheme of alkenes.

1. i. For each reaction scheme, give the structure of major product.
ii. State the RULE used to determine the major product.

CH3 CH3

H3CC CH2CH3 H3CCHCHCH3 Anti Markovnikov's rule

CH3 Br Br

H3CC CH2CH3 Markovnikov's rule O CH3
2

Cl HBr H H3CC CHCH3
Markovnikov's rule HCl 2

CH3 HBr, Br2, CH2Cl2 Br Br

H3CCH CH2CH3 H2, Pt CH3 Cl2, CH2Cl2 CH3
H3CC CHCH3 H3CC CHCH3
Ni Cl2 , H
CH3 H , 2O Cl Cl

2

H3CCH CH2CH3 Pd H 2O, H+ CH3
H3CC CHCH3
CH3 ,
H3CCH CH2CH3 OH Cl
H
2

CH3
H3CC CH2CH3

OH

Markovnikov's rule

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PRACTICE MODULE CHAPTER 5 SK025

2. (a) i. Give the IUPAC name for the alkene.
ii. Based on the structure of product given, give the reagent for each reaction.

CH3
OH

CH3

+

H

H 2, Ni O, Cl

CH3 H CH3
Br 2 OH

HBr Cl2, H2O

CH 2Cl 2 CH3 HBr, H O Br
2 2 CH3
, IUPAC Name =
Cl Cl2
2 1-methylcyclopentene

Cl CH Br 2, H 2O
CH3 2

,

Br2

Cl Br CH3
CH3 OH

Br

Br

(b) Propose the mechanism for the following reaction:
i. Acid catalysed hydration of 1-methylcyclopentene.
ii. Addition of hydrogen bromide to 1-methylcyclopentene.

Answer:

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PRACTICE MODULE CHAPTER 5 SK025
b(ii) : Addition of hydrogen bromide to 1-methylcyclopentene

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PRACTICE MODULE CHAPTER 5 SK025

3. Complete the reaction scheme below.

CH(CH3)2

CH(CH3)2 CH2CH3 CH(CH3)2
Br Cl

OH Cl

HO Br Br2 H2/Pt Cl
CH2CH3 Cl
, H O
2 CH2CH3
2Cl 2

Cl , CH

2

CH(CH3)2 CH(CH3)2 HBr, (CH3)2O2 Br CH(CH3)2
CH2CH3
OH H2O, H+

HO

CH2CH3

2O HBr Br

H CH2CH3

,

Cl
2

CH(CH3)2 CH(CH3)2
Cl Br

OH Br

HO CH2CH3

Cl

CH2CH3

WORKSHEET 5.2. k, l
Draw the structure of product(s).

1.

i. O3 O
ii. Zn, H2O
+O

KMnO4, H+ O

+O

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PRACTICE MODULE CHAPTER 5 SK025

2. i. O3 CH3 H
ii. (CH3)2S CO
CH3 + O C CHCH3
C CHCHCH3 KMnO4, H+
 CH3
CH3

CH3 OH
CO
+ O C CHCH3

CH3

Draw the structure of an alkene KMnO4, H+ OO
1.  H3C C CH2CH2CH2C OH

H3C i. O3 OO
ii. Zn, H2O H3C C CH2CH2CH2CH
2.

KMnO4, H+ OO + OO
 H3C C CH2CCH3 HO C CH C OH

CH3

i. O3 OO + OO
ii. Zn, H2O H3C C CH2CCH3 H C CH C H

CH3

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PRACTICE MODULE CHAPTER 5 SK025

WORKSHEET 5.2. m
1. What is Baeyer’s reagent?

2. a) Give the observation for each pair compounds given below with :
i. Baeyer’s Test
ii. Bromine in dichloromethane (in the dark)
iii.Bromine water (in the dark)

b) Write the equation reaction for each pair compounds.
Reagent Baeyer’s Test :

i. 2-butene and butane Butane
Observation:

2-butene

Equation Equation

ii. cyclopropane and 3-cyclopropyl-1-propene

Observation : cyclopropane Observation :3-cyclopropyl-1-propene

Equation Equation

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PRACTICE MODULE CHAPTER 5 SK025

iii. pentane and 1,3-pentadiene

Observation : Pentane Observation : 1,3-pentadiene

Equation Equation

iii.Bromine water (in the dark) Butane
Reagent :

i. 2-butene and butane
Observation:

2-butene

Equation Equation

ii. cyclopropane and 3-cyclopropyl-1-propene

cyclopropane 3-cyclopropyl-1-propene

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PRACTICE MODULE CHAPTER 5 SK025

iii. pentane and 1,3-pentadiene Observation : 1,3-pentadiene
Observation : Pentane

WORKSHEET 5.2
MULTIPLE CHOICE QUESTIONS
Answer ALL the questions

1. What is the IUPAC name of the following compound?

A. cis-4-ethyl-3-octene
B. trans-4-ethyl-3-octene
C. cis-4-butyl-3-hexene
D. trans-5-ethyl-5-octene
2. Which among these is not a structural isomer of the compound C4H8?
A. But-1-ene
B. But-2-ene
C. But-3-ene
D. 2-methylpropene

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PRACTICE MODULE CHAPTER 5 SK025

3. Identify the addition reaction which is not undergone by the alkenes?
A. Hydrogenation
B. Hydrohalogenation
C. Acid Catalyst Hydration
D. Halogenation with iron(III) chloride

4. Which among the following is not same phase at room temperature?
A. 1-Hexene
B. Ethene
C. Propene
D. 1-Butene

5. 4-chlorobut-1-ene is the name of which among the following alkenes?
A. CH2Cl-CH2=CH-CH2
B. CH2Cl-CH2-CH-CH2
C. CH2Cl=CH2-CH=CH2
D. CH2Cl-CH2-CH=CH2

6. Which of the following alkenes gives a main product different from the products from
the others in reactions with hydrogen chloride?

A.

B.

C.

D.

7. Cis-trans isomerism in alkenes is due to
A. chiral carbon
B. free rotation about single bond
C. free rotation about the double bond
D. restricted rotation about the double bond

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PRACTICE MODULE CHAPTER 5 SK025

8. The number of structural isomers of alkenes with the molecular formula C4H8 is.
A. 2
B. 3
C. 4
D. 5

For the questions 9 and 10 ,follow this options

A B CD
I only I and II II and III I, II and III

9. Which of the following statements true about the dehydration of alcohol?
I. Alkene and water will produced.
II. Hot concentrated phosphate acid used as reagent.
III. Markovnikov’s rule is used to determine the major product.
Answer :

10. Choose the correct arrangement increasing order of boiling point.
I 1-pentene<2-methyl-1-butene<2-methyl-2-butene
II 1-pentene< trans-2-pentene<cis-2-pentene
III ethene< propene<1-butene
Answer :

WORKSHEET 5.2

MODEL OF PSPM QUESTIONS

1. Compound D undergoes ozonolysis to give mixture of 2-butanone (CH3COCH2CH3) and
Propanal (CH3CH2CHO). Compound D also reacts with one mole equivalent of hydrogen
gas to form saturated compound E.

a). Suggest the structural formulae for compounds D and E. Give an explanation to support
your answer.
b). Suggest a chemical test to differentiate compound D from E. Indicate the observation and

write chemical equation involved.

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PRACTICE MODULE CHAPTER 5 SK025
2. Alcohol can be used as the starting material in synthesizing various organic compounds

as shown in the reaction scheme below. Propose the structures for P and Q.

Give the mechanism for the formation of Q.
3. Reaction of A (2-ethyl-1-pentene ) with several reagents are shown below:

a). Draw the structures of B, C, D and E.
b) Suggest any alkyl halide and suitable reaction condition to produce A.

Prepared by : Mdm Siti Afiza Basir
Checked by : Siti Fadhilah Ayub

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PRACTICE MODULE CHAPTER 6 SK025

CHAPTER 6: BENZENE & ITS DERIVATIVES

6.1 INTRODUCTION
I-think map

WORKSHEET 6.1
1. How many pi(ᴨ) electrons are contained in each molecule?

a) b) c) d)

Answer: Answer: Answer: Answer:
a) b) c) d)

2. Which of the following compounds are aromatic? Assume they are all planar. For any
compound that is not aromatic, state why this is so.

a) b) c)

Answer: Answer: Answer:

3. By using Huckel’s rule, determine which of the following compound is/are aromatic?
-
+ Answer:

P QR S

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PRACTICE MODULE CHAPTER 6 SK025

6.2 NOMENCLATURE OF BENZENE AND ITS DERIVATIVES

WORKSHEET 6.2 c)
1. Name the following arenes:

a) b)

2. Name the following compounds. OH c) F
a) b) Cl

O CH3
C

Br

d) e) f)

OHC CH3 Br OH
Br
CH H2N
CH2 COOH

CH3

NH2

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PRACTICE MODULE CHAPTER 6 SK025

g) h) i)

OCH 3 CH3 NH2

NO2 NH2

CH(CH 3)2

j) k) l)

NH2 CH3
OH H3C C COOH

COOH
OH

3. Draw a structure corresponding to each name

a) 3-benzyl-1-hexanol b) m-diethylbenzene c) p-bromochlorobenzene

d) 1,4-dinitrobenzene e) 1,2-benzenediol f) 1,4-diaminobenzene

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PRACTICE MODULE CHAPTER 6 SK025

g) 3-aminobenzoic acid h) m-bromoaniline i) p-bromotoluene

k) 2-phenyl-1-butene l) 3-phenylcyclohexanol m) 2-methyl-3-phenyl-1-
butanol

n) 2,4-dimethoxyphenol o) 2-phenyl-propan-1-ol p) Benzyl methyl ether

q) 2-nitrophenol r) 3,5- 3-bromo-1-pheyl-1-butene
dimethylbenzaldehyde

4. (a) Draw and name all the isomeric of the benzenes (molecular formula C6H4Cl2)
Answer:

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PRACTICE MODULE CHAPTER 6 SK025
(b) Draw and name all the possible isomers for o-bromophenol
Answer:

6.3 CHEMICAL PROPERTIES OF BENZENE
I-think Map

1. Reaction of benzene involved nitration, halogenation, Friedel-Crafts Acylation, Friedel-

Crafts Alkylation and substitution of side chains.

2. Activating group increases the reactivity of benzene ring while deactivating group

decreases the activity of benzene ring.

3.

Group Ortho-Para director Meta director

Activating group -NH2, -NHR, -NR2, -

-OH,-OR,-C6H5,-R

Deactivating group -Cl, -Br, -I -NO2, -CN-, -COOH, -

COOR, -CHO, -COR, -

SO3H

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PRACTICE MODULE CHAPTER 6 SK025

WORKSHEET 6.3

1. Why does alkene undergo electrophilic addition whereas benzene reacts with electrophiles
by substitution?

Answer:

2. Give the product(s) formed when benzene is treated with the following alkyl halide in the
presence of lewis acid catalyst Aluminum Chloride?

a) CH3CH2CH2Cl
b) 2-chlorobutane
c) chlorocyclopentane
Answer:

3. Draw the product formed when benzene is treated with the following acyl chloride in the
presence of AlCl3?

Answer:

a) O O

+ CH3 CH2 C Cl AlCl3 C
CH3CH2

b) O O
C
+ C Cl AlCl3

c) CH3 O CH3 O

+ CH3 C C Cl AlCl3 H3C C C

CH3 CH3

d) O O
C
+ C Cl AlCl3

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PRACTICE MODULE CHAPTER 6 SK025

5. Nitration and Bromination of benzene is shown in the following reaction scheme:

conc. HNO3, conc. H2SO4 CH3Cl Br2 C

A 50-55 °C B uv

Answer: AlCl3

(i) Give the structure of A, B and C. C:
A: B:

(ii) State the type of reaction involved to form A & B.

(iii) What is the function of H2SO4?

(iv) Identify and name the electrophile in the nitration of benzene.

(v) State the observation when a mixture of B and bromine is exposed to sunlight.

6. Based on the following reactions; F
A

B Br2 Cl2 FeCl3 Cl2 FeCl3
H
O FeBr3 CH3Cl CH2 Cl
CH3 D
AlCl3
K2Cr2O7, H+
G

conc.HNO3 , 50 - 55 °C
conc. H2SO4

CE

a) Draw and name the compound formed for A, B, C, D and E

b) What is the suitable reagent used for G & H?
Answer:

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PRACTICE MODULE CHAPTER 6 SK025

c) Name the reaction for the formation of compound C and D?
Answer:
C=
D=

7. Give the complete chemical equation for the bromination of benzene and cyclohexene. It
said that both reactants undergo different types of reaction. Explain your answer.
Answer:

Explanation:

8. Identify the following compounds from P to T

CH2Cl

CH3

(i) R

CH3Cl P CH3
Q
+T
(ii) S

Cl

Answer:
a) State the type of the reaction that occurs in reaction (i) and (ii).

Reaction (i):
Reaction (ii):

b) Write the chemical equation for the reaction of toluene with hot acidified K2Cr2O7
solution.

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PRACTICE MODULE CHAPTER 6 SK025
c) State whether tertbutyl benzene can undergo the reaction stated in (b). Explain.

9. Write the equation and name the product of
a) Bromination of phenol
b) Nitration of benzaldehyde

Answer:
a)

b)

10. Compare the reaction rate of nitration for the following compounds. Explain
a)

CHO CH3 Br

,,

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Rate: PRACTICE MODULE CHAPTER 6 SK025
Explanation:

11.
b)

COOH NH2 OH

, ,

Rate: Explanation:

12. Compound T is formed from the reaction of benzene with chloroethane in the presence of
AlCl3. Chlorination of T in light gives monochlorinated compound U (major product) and V.
Treatment of T in acidified solution of KMnO4 produces W. Refer to this, complete the
reaction scheme below.

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PRACTICE MODULE CHAPTER 6 SK025

CH2 CH3 COOH

+ CH3CH2 Cl AlCl3 KMnO4, H+, W

T
Cl2, uv

Cl CH2 CH2 Cl
CH CH3

+

U V

major product

Name the reaction for the formation of T:

Name the type of reaction for the formation of U & V:

Complete the mechanism below, use curved arrows to indicate movement of electrons:

Answer:

Step 1: Formation of complex

Step 2: Formation of arenium ion

Step 3: Deprotonation
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PRACTICE MODULE CHAPTER 6 SK025
13. A, an aromatic hydrocarbon with molecular C8H10, oxidises to produce carboxylic acid B.

Esterification of B by ethanol forms ethyl benzoate. A form 2 monosubstituted chlorinated
products; C and D, with Cl2 in the presence of light. D, is the major product. Identify A-F.
Answer:

14. Acid catalyst sulphuric acid role is to help to produce electrophile in nitration reaction.
Show the mechanism of the reaction.

Answer:

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PRACTICE MODULE CHAPTER 6 SK025
15. Benzene undergoes Friedel-Crafts alkylation with 1-chloropropane to form

isopropylbenzene. Give the mechanism for this reaction.
Answer:

WORKSHEET 6.4
1. Outline the synthesis for the following reactions:
Answer:

a) nitrobenzene from benzene
b) chlorobenzene from benzene

c) bromobenzene from benzene

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PRACTICE MODULE CHAPTER 6 SK025
d) benzoic acid from benzene

2. By using benzene, outline a reaction scheme to synthesis the following compounds:
Answer:
a) Aniline

b) Isopropylbenzene

c) i) tert-butylbenzene

ii) State whether tert-butylbenzene can undergo the reaction with hot, acidified
potassium dichromate solution. Explain.
Answer:

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PRACTICE MODULE CHAPTER 6 SK025
3. By using ethylbenzene, show the synthesis of 1-phenyl-1,2-ethanediol
Answer:

4. Starting from toluene, outline the step/steps involved to prepare;
Answer:

(i) 4-nitrocarboxylic acids

(ii) 2-phenylethanoic acid

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PRACTICE MODULE CHAPTER 6 SK025
5. Starting from either benzene or toluene, complete the following steps to synthesis 2-

nitrobenzoic acid, 3-nitrobenzoic acid and 2-methylaniline.
Answer:
2-nitrobenzoic acid

3-nitrobenzoic acid

2-methylaniline

WORKSHEET 6.5
1. Suggest chemical test to differentiate between the following pairs:
a) Benzene and cyclohexene
b) Toluene and benzene
Answer:
a) Chemical Test:
Chemical equation:

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PRACTICE MODULE CHAPTER 6 SK025

Observation:
Chemical equation:

@ Observation:
a) Chemical Test:

Chemical equation:

Observation:
Chemical equation:

Observation:
@

a) Chemical Test:
Chemical equation:

Observation:
Chemical equation:

Observation:

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PRACTICE MODULE CHAPTER 6 SK025

b) Chemical Test:

Observation:

Observation:

WORKSHEET 6.6
MULTIPLE CHOICE QUESTIONS

1. Which statement about property of benzene is incorrect?
A. It is a planar molecule.
B. Each C atom is sp hybridized
C. Its typical reaction is electrophilic substitution
D. It is stabilised by delocalisation of pi electrons.

2. Which statement about the reaction of benzene with Cl2 in the presence of AlCl3 is incorrect?
A. The name of reaction is halogenation
B. Chlorobenzene is formed
C. The type of reaction is electrophilic addition
D. AlCl3 is a catalyst.

3. Which of the following statements is FALSE about characteristics of an aromatic
compounds?
A. are planar
B. have 4n ᴨ-electrons
C. are cyclic
D. are completely conjugated

4. Name the following compound

A. m-diethylbenzene
B. 3-propylethylbenzene
C. 3- propyltoluene
D. 1-ethyl-3-propylbenzene

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