PRACTICE MODULE CHEMISTRY DK024

UNIT KIMIA, KELANTAN
MATRIKULASI
CHEMISTRYPRACTICE MODULEKOLEJ
DK024 2021/2022

Revised By, NOKOARMANRAUJDIHDAINH
FABDSATHHHAAYRARIFUHADHSDYINED
FNAZORAOAHNRBAADNARUASINLMALUAAMHSHAAANPNAIANI

SEKALUNG

PENGHARGAAN

Alhamdulillah syukur kehadrat ILAHI kerana

diberi peluang dan masa oleh Allah SWT untuk
menyiapkan Buku Extra Exercise DK024
ini.Tanpa sumbangan dan komitmen insan-insan
yang disenaraikan di bawah ini, pastinya buku ini
tidak mampu disiapkan dengan jayanya.

FARHANA UMANAN
ZANARINA SAPIAI
NOOR ASMAHAN ABDULLAH
NOOR NAJIHAH KAMARUDDIN
SHARIFAH FADTHYAH SYED

BAHARUDDIN
Justeru itu, diharapkan semua anak didik
yang dikasihi dapat memanfaatkan buku ini
dengan sepenuhnya dalam membuat ulangkaji
subjek Kimia Organik dan seterusnya
memperolehi keputusan yang cemerlang dalam
PSPM Sem 2 yang bakal menjelang nanti.
Akhir kalam, Selamat Mengulangkaji dan

Selamat Maju Jaya.

ii

LIST OF CONTENT Page
1
No Chapter 14
1 Introduction To Organic Chemistry 28
2 Alkane 38
3 Alkene 48
4 Aromatic Compound 61
5 Alcohol 74
6 Carbonyl
7 Carboxylic acid

i

EXTRA EXERCISE MODULE CHAPTER 1 2020/2021
CHAPTER 1 : INTRODUCTION TO ORGANIC CHEMISTRY

1.1 : INTRODUCTION AND STRUCTURAL FORMULAE
WORKSHEET 1.1

1. Write an expanded structure for each of the following hydrocarbons:
(a) propane, C3H8

(b) propene, C3H6 (has one double bond)

(c) propyne, C3H4 (has one triple bond)

(d) cyclopropane, C3H6 (cyclic structure)

2. Write an expanded structure for each of the following hydrocarbons:
(a) butane, C4H10

(b) pentane, C5H12

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EXTRA EXERCISE MODULE CHAPTER 1 2020/2021

(c) cyclobutane, C4H8 (cyclic structure)

(d) cyclobutene, C4H6 (cyclic structure and has one double bond)
3. Write a condensed structural formula for 2,3–dimethylpentane.

4. Convert the following condensed structures into expanded structure:
(a) CH3CH2COOH
(b) CH3COCH2Br
(c) (CH3)3COH

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EXTRA EXERCISE MODULE CHAPTER 1 2020/2021

(e) (CH3)3CCHO

(e) CH3COCl

5. Outline the C skeleton of the following condensed structure formula and then write each as a skeletal
structure:

(a) (CH3)2CHCH2CH3
(b) (CH3)2CHCH2CH2OH
(c) (CH3)2C═CHCH2CH3

(d) CH3CH2CH2CH2CH3
(e) CH3CH2CHOHCH2CH3

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EXTRA EXERCISE MODULE CHAPTER 1 2020/2021

(f) CH2═C(CH2CH3)2

(g) CH3COCH2CH2CH2CH3

(h) CH3(CH2)2C(CH3)2CH(CH3)CH(CH3)CH(Br)CH3

WORKSHEET 1.2
1. Classify the carbon atoms in each compound as 1o, 2o, 3o, or 4o.

a. CH CH CH =

323

b.
(CH ) CH =

33

c. =
d. =

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EXTRA EXERCISE MODULE CHAPTER 1 2020/2021

WORKSHEET 1.3

1. Classify each of the following compounds as an alkane, alkene, alkyne, alcohol, aldehyde,
amine, and so forth.

a. O
= ______________________

b. CH –C≡CH = ________________________

3

O
c. = ____________________________

H
d. OH

= ____________________________

e. = _________________________________
OH

f. CH (CH ) (CH ) CH = __________________________

3 27 2 12 3

H H

2. Determine the functional group of the following compounds.
a.

O
= _________________________

OH

b. O

OCH = _______________________________

3

c. = _____________________________

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EXTRA EXERCISE MODULE CHAPTER 1 2020/2021

d.
N(CH3)2 = _______________________

e. CH = __________________

3

CH —C—CHCH

33

CH Cl

3

3. Circle and name the functional groups, and name the class of following compounds.

a. O

Functional group : __________________________

CH CH –C–CH
32 3 Class : __________________

b.
O

Functional group : ___________________

CH CH –C–OH Class : ________________________

32

C. CH CH CH –CN Functional group : ___________________
Class : _____________________
322
Functional group : ______________________
d. Class : __________________

CH CH –O–CH CH
32 23

e. CH CH CH –NH Functional group : _______________
322 2 Class : _______________

f. CH Functional group : _______________________
Class : _____________________________
3

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EXTRA EXERCISE MODULE CHAPTER 1 2020/2021

WORKSHEET 1.4
Identify (circle) the functional groups in the following molecule:

a. H
N

CH O H
N
3
O
melatonin
(hormone thought to induce sleep)

b. aspartame (synthetic sweetener)

O O CH 2

HO–C–CH C N CH O
2C C
HH CH
HN
3
2
O

c. Vitamin E CH CH CH
CH
3 3 3
3
O

(CH CH CH CH) –CH
222 3 3

HO

7

EXTRA EXERCISE MODULE CHAPTER 1 2020/2021

WORKSHEET 1.5
1. How many structural isomers does pentane, C5H12, have?. Draw all the isomers.

2. Write structural formulas for all the constitutional isomers with the molecular formula C7H16.
(Hint: Total = 9 isomers)

3. Propose structures for five isomers with the formula C7H8O.

8

EXTRA EXERCISE MODULE CHAPTER 1 2020/2021

WORKSHEET 1.6
1. Classify each of the following reactions as an addition, elimination, substitution, or rearrangement:

(a) CH3Br + KOH → CH3OH + KBr
(b) CH3CH2OH → H2C═CH2 + H2O
(c) H2C═CH2 + H2 → CH3CH3
(d) CH2═CHOH → CH3CHO
(e) CH3C≡CH + HCl → CH3CCl═CH2
(f) (CH3)2C═O + NaCN → (CH3)2C(OH)CN
(g) CH3CH2CH2Br + KOH → CH3CH═CH2 + HBr
(h) CH3CH2CH2Br + NaCN → CH3CH2CH2CN + NaBr

2. Classify each of the following reactions as an addition, elimination, substitution, or rearrangement:

3. Classify each transformation as substitution, elimination, or addition.

OH Br
a. HBr

b.
H2 /Pt

c.

CH CH CH(OH)CH Conc H2SO4 CH CH═CHCH

32 3 33

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EXTRA EXERCISE MODULE CHAPTER 1 2020/2021

c.
NaOH/ methanol

WORKSHEET 1.7

MULTIPLE CHOICE QUESTIONS

Answer ALL the questions

1. Which of the following compounds is not organic?

A CH4 C CO

B C2H2 D CCl4

2. Which molecular chemical bond found commonly in organic compounds?

A Hydrogen Bond C Ionic Bond

B Van Der Waals Force D Covalent Bond

3. What are the Aliphatic Hydrocarbons?

A Open chained carbon hydrogen organic compounds
B Cyclic chained carbon hydrogen organic compounds
C Straight chained carbon hydrogen and some other elements organic compounds
D Closed chained carbon hydrogen and some other elements organic compounds

4. What is the product formed when an organic compound is bunt?
A Carbon dioxide
B Hydrogen peroxide
C Carbon Sulfide
D Hydrogen Sulfide

5. Which compound is not an ether?

A CH3CH2OCH2CH3
B CH3COCH2CH3
C

D

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EXTRA EXERCISE MODULE CHAPTER 1 2020/2021

WORKSHEET 1.8
MODEL OF PSPM QUESTIONS
1. Redraw the following structure, then circle and name all the functional groups:

O

OH

C OH
O

2. Name the type of reaction for steps A, B, C and D in the following scheme:

COOH COCl COCl
CH = CH2
CHCH3 SOCl2 KOH / Alcohol
Br A
CHCH3 B
Br
Answer :
C H2O / H+ A – ____________
B- _____________
COCl COCl C – ____________
OH
CHCH3 catalyst
OH D CH2CH2

3. The structure of paracetamol is shown below. Redraw the structure, then circle and name all the
functional groups that exist.

O
HO NH C CH3

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EXTRA EXERCISE MODULE CHAPTER 1 2020/2021

4. Arrange the following species in order of increasing stability. Explain.

CH3 CH CH2 CH CH3 CH3
+
2 2

CH3 C C CH3
+

C+H3

Answer :

5. Consider the following molecular structure:
OH

a
b

Cl

a. Classify the carbons labeled a and b as primary, secondary or tertiary.
Answer : A – ______________
B – ______________

6. a. Redraw the following structure, then circle and name all the functional groups.

NH2

NO2

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EXTRA EXERCISE MODULE CHAPTER 1 2020/2021

a. State the number of 1o,2o and 3o carbon(s) in the compound below
Answer : primary = ___________ secondary = __________ tertiary = _____________

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EXTRA EXERCISE MODULE CHAPTER 2 2020/2021
CHAPTER 2 : ALKANE

2.1 : STRUCTURE AND NAMING OF ALKANE
WORKSHEET 2.1

1. Name this following alkane with correct IUPAC name.

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EXTRA EXERCISE MODULE CHAPTER 2 2020/2021

2. Draw the structural formula for the following molecules.
a. 4-ethyloctane
b. 2-methylnonane
c. 3,3-dimethylpentane
d. 3-ethylpentane
e. 3-ethyl-2-methylheptane

f. 2,2,3-trimethyl-butane

g. 3-ethyl-2,2-dimethyl-hexane

15

EXTRA EXERCISE MODULE CHAPTER 2 2020/2021

WORKSHEET 2.2
For each alkane write the correct IUPAC name.

1. CH3CH2CH2CH3 = ________________________
2. CH3CH(CH3)CH3 = _______________________

3. = _____________________

4. = _____________________

5. = ________________________

6. = ________________________
7.

= _____________________

= ____________________________
8.

= ______________________________

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EXTRA EXERCISE MODULE CHAPTER 2 2020/2021

9. = ________________________________

10. = ______________________________

= ______________________________
WORKSHEET 2.3
Draw the structure for the following IUPAC name.

1. 2-methylpentane -

2. 2,2-dimetylbutane -

3. 4-ethyl-3-methylnonane

4. 2,3,4-trimethylheptane -
5. 4-butyl-6-ethyl-2,5-dimethylnonane -

17

EXTRA EXERCISE MODULE CHAPTER 2 2020/2021

6. Octane =

7. 2,3-dimethylbutane =
8. 3,3-dimethylhexane =

9. 3-ethyl-3-methylhexane =
10. 5,5-diethyl-2,2,4,4-tetramethyloctane =

WORKSHEET 2.4

1. Give the IUPAC name for each compound

a. CH CH CH c.
CH 32 CH—3 CH3 ______________________________
3

— CH—

______________________

b.

________________________ d.
___________________________________

18

EXTRA EXERCISE MODULE CHAPTER 2 2020/2021

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 - _______________________________
(f) (CH3)2CHCH2CH2CH(CH2CH3)2 - ________________________________
(g) (CH3)2CHCH(CH3)CH2C(CH2CH3)2CH3 - _____________________________
(h) (CH3)2CHC(CH2CH3)2CH2CH2CH3 – ________________________________

2.2 SOURCES, PHYSICAL AND CHEMICAL PROPERTIES OF ALKANE
WORKSHEET 2.5

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.

19

EXTRA EXERCISE MODULE CHAPTER 2 2020/2021

WORKSHEET 2.6
1. In each pair of compounds, which compounds has the higher boiling point?
Explain.
(a) octane or 2,2,3–trimethylpentane

(b) heptane or 2–methylnonane

(c) 2,2,5–trimethylhexane or nonane

2. Without referring to tables, list the following hydrocarbons in order of decreasing boiling
Points. Explain.

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

pentane

Answer :

Decreasing boiling point

20

EXTRA EXERCISE MODULE CHAPTER 2 2020/2021

3. Rank the the compounds in the following groupin order of increasing boiling point?
OH O

H

WORKSHEET 2.7
1. Rank the following compounds in order of increasing water solubility. Explain.
(CH3)3CH , CH3OCH2CH3 , CH3CH2CH2CH3 , CH3CH2CH2OH

2. Which compounds are water soluble?

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

Answer :

21

EXTRA EXERCISE MODULE CHAPTER 2 2020/2021

WORKSHEET 2.8

1. C(aom) pleCtHe thCeHfoClloHwing+comObustiofnlarmeaection equations:
323 2

(b) flame

+O 2

flame

(c) CH3CH2CH2CH2CH(CH3)2 + O

2

_______________________________________________________________________

(d) flame

7CO2 +
__________________8_H_2O___________________________________________

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

on the basis of this information, deduce the structure of each alkane.

a. CH4 + Cl2 uv ____________________________

uv

b. CH3CH3 + Cl27CO2 + ___________________________
8H2O ___________________________
7CO2 +

c. + Cl28H2Ouv

d. _______
_______
_u_v

+ Cl2 ______________________________

_ 7CO2 +

8H2O

7CO2 +

8H2O

22

EXTRA EXERCISE MODULE CHAPTER 2 2020/2021

WORKSHEET 2.9

MULTIPLE CHOICE QUESTIONS

Answer ALL the questions

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

For the questions 4 and 5 ,follow this options

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

4. 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 :

5. Pick the true statements 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 :

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EXTRA EXERCISE MODULE CHAPTER 2 2020/2021

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

WORKSHEET 2.7
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.
Answer

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EXTRA EXERCISE MODULE CHAPTER 2 2020/2021

2. The structure of compound I, II, and III are shown below.

CH3CH2CH2CH2CH3 CH3C(CH3)2CH3 CH3CH2CH(CH3)CH3
I II III

Arrange these compound in order of decreasing order of boiling point. Explain your answer.
Answer :

[10 marks]

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

CH3

H3C CH3

Cl
(1 mark)

Answer : ____________________________________________

b. Arrange the following compound in order of increasing boiling point. Explain.
pentane , 2,2-dimethylbutane , 2-methylbutane

Answer : ___________________________________________________________________
Explain :

25

EXTRA EXERCISE MODULE CHAPTER 2 2020/2021

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 :
________________________________________________________

4. a. The following names are all incorrect, but they represent the real structure. Name the compound
correctly.
i. 2-cyclohexylbutane
answer : ___________________________________
ii. 1,2,2-trimethylcyclopentane
answer : _____________________________________
b. If 25 ml of hexane were added to 100 ml of water in a beaker, what would you expect to
happen? Explain.

26

EXTRA EXERCISE MODULE CHAPTER 2 2020/2021

c. Alkanes known as paraffin are saturated hydrocarbon.
i. Explain why alkane are generally unreactive
___________________________________________________________________________
ii. State the natural source of alkane.
_____________________________________
d. Ethane can react with chlorine with the presence of ultraviolet to form chloroethane

Write equation for initiation and propagation step
i. Chain initiation step

ii. Chain propagation step

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

27

EXTRA EXERCISE MODULE CHAPTER 3 2020/2021

CHAPTER 3: ALKENES

STRUCTURE AND NAMING OF ALKENES

WORKSHEET 3.1

Give the IUPAC names for the following alkenes:

i. CH3CH2CH=CH2 CH3
ANSWER: iii.

ii. H3C H Cl
C ANSWER:
C
H CH2 CH2CH3

ANSWER:

iv. CH3 CH3
H2C C CCH3

CH3 ANSWER:

WORKSHEET 3.2

Draw the structural formula for each of the following alkenes:

(i) 4,5-dibromo-1-heptene ANSWER:

(ii) trans-2-hexene ANSWER:

(iii) 3-methylcyclopentene ANSWER:

(iv) 1-isopropyl-4-methylcyclohexene ANSWER:

WORKSHEET 3.3

Decide whether the following structures are named correctly according to the IUPAC rules. If a name
is incorrect or ambiguous, assign the correct name:

28

EXTRA EXERCISE MODULE CHAPTER 3 2020/2021

i.
1-methyl-2-cyclohexene

ANSWER:
ii. CH2=CHCH2Cl 1-chloro-2-propene

ANSWER:

PREPARATION OF ALKENES
WORKSHEET 3.4
1. Draw the product of the following reactions. When more than one product is expected, determine which

one will be the major product.
CH3 conc. H2SO4
OH



ANSWER:

2. Show the products of these reactions;

i. OH

conc. H3PO4



ii. OH
CHCH3 conc. H2SO4



Cl

iii. CH3 conc. H2SO4
H3C C CH3
OH 

29

EXTRA EXERCISE MODULE CHAPTER 3 2020/2021

3. Starting with cyclohexanol, describe how you would prepare cyclohexene
ANSWER:

REACTION IN ALKENES
WORKSHEET 3.5
1. What product would you obtain from catalytic hydrogenation of the following alkenes?

a. CH3
H3C C CH CH2CH3

b. CH3
CH3

c. 1-butene CH2
d. CH3

with excess H2
2. Give the major product obtained from the reaction of HCl with each of the following

a) CH3
CH3C CHCH3

b) CH3CH CH2 CH CH2
CH3

c) CH3

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EXTRA EXERCISE MODULE CHAPTER 3 2020/2021

3. What will the major product of the reaction of 2-methyl-2-butene with each of the following reagents
a) HBr
b) HCl
c) HBr, peroxide
d) HCl, peroxide

ANSWER:

4. Give the major product obtained from the acid catalyzed hydration of each of the following alkene?
a)
CH2

b) 1-hexene CH3
c) CH2

CH3
d) CH2 C CH2 CH CH3

CH3
5. Draw the product of each reaction.

a) Br2, CH2Cl2

b) Cl2

CH2Cl2

c) Br2, CH2Cl2
CH CHCH3

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EXTRA EXERCISE MODULE CHAPTER 3 2020/2021

6. Draw a synthesis of 1,2-dibromocyclohexane from cyclohexanol
ANSWER:

7. Provide the reagents necessary to complete the following transformation. The synthesis may

involve more than one step.

OH OH
?

OH

ANSWER:

MECHANISM HYDROHALOGENATION

WORKSHEET 3.6

1. Outline mechanism for the electrophilic addition
a) HCl to 2-methyl-2-butene
b) HBr to 1-methylcyclopentene

ANSWER:

32

EXTRA EXERCISE MODULE CHAPTER 3 2020/2021

MINDMAP IN ALKENES
WORKSHEET 3.7
1. Draw the structural formulae of compounds A, B, C, D, E, F, and G in the following reactions:

A

G KMnO +

4 , OH - H2O, H

cold cold H3C CH3 Br2, CH2Cl2

conc. H2SO4 CH3 B
HCl
F

HBr, ROOR

E H2, Pt C

D
A

G KMnO +

4 , OH - H2O, H

conc. H2SO4 H3C C CH2 Br2, CH2Cl2
CH3
F B

HBr, ROOR HCl

E H2, Pt C

D

33

EXTRA EXERCISE MODULE CHAPTER 3 2020/2021

WORKSHEET 3.8
MULTIPLE CHOICE QUESTIONS
1. When two carbon atoms share two electron pairs then they form

A. single bond
B. double bond
C. triple bond
D. coordinate covalent bond

2. What is the color of bromine?
A. Brown
B. red
C. orange
D. Reddish brown

3. Baeyer’s reagent is used to detect
A. glucose
B. double bond
C. oxidation
D. reduction

4. All the following reactions are example of addition reaction except
A. Reaction of Cl2 with propene.
B. Reaction of HBr with but-2-ene
C. Combustion of propene.
D. Catalytic hydrogenation of 2-butene

5. HBr can be added to an alkene in the presence of peroxides (ROOR). What function does
the peroxide serve in this reaction?

34

EXTRA EXERCISE MODULE CHAPTER 3 2020/2021

A. nucleophile
B. electrophile
C. Radical chain initiator
D. catalyst

WORKSHEET 3.9
MODEL OF PSPM QUESTIONS
1.Consider the following reaction scheme.

OH

Alkene CH3CH2CCH2CH3
CH3
[7 marks]

F

a. Give the IUPAC name for F.

ANSWER:

b. Suggest one possible alkene to produce F and give the suitable reagent for this conversion.

ANSWER:

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 .

H CH3 conc. H2SO4 HCl Q
HOCH2 C C CH3
P
HH

ANSWER:

35

EXTRA EXERCISE MODULE CHAPTER 3 2020/2021

3. Compound A has a molecular formula of C7H14. A reacts with bromine in dichloromethane to
form 1,2-dibromo-3,4-dimethylpentane. Treatment of A with HCl gives B and C.

a. Draw the structural formulae of A, B and C.
b. Draw the structures of the carbocation intermediates in the formation of B and C.
c. Name the type of reaction for the formation of B and C.

ANSWER:

4. Dehydration of 3-methyl-2-butanol gives a number of isomeric alkenes. Give the suitable
reagent and condition that can be used for the above reaction. Draw the structures of all isomeric
alkenes formed. Indicate the major product and explain your answer.

ANSWER:

5. Propose a chemical test to differentiate 2-methylpropane from 2-methylpropene.
a. State the observation and write the reaction equation
ANSWER:

b. 2-methylpropene can be prepared from alcohols, suggest the suitable alcohols for this preparation
and name the reaction involved.

ANSWER:

6. a. Name the following compounds according to IUPAC nomenclature.

i) ii)
ANSWER:

36

EXTRA EXERCISE MODULE CHAPTER 3 2020/2021

b. Draw the structural formulae of the compounds below;
i) 2-Bromo-3-methyl-2-butene
ii) 2,4-Dimethyl-2-hexene

ANSWER:

c. The reaction scheme below shows reactions of 2,3-dimethylcyclobutene.
A

conc.H2SO4


H2 H3C CH3 K H3C CH3
pt H
B
Br
2,3-dimethylcyclobutane

HCl Br2, CH2Cl2

C D
i. Draw the structure of A, B, C and D.

ANSWER:

ii. Name the reaction for the formation of B.
ANSWER:

iii. State the rule used to determine structure C.
ANSWER:

iv. State the reagents K
ANSWER:

37

EXTRA EXERCISE MODULE CHAPTER 4 2020/2021

CHAPTER 4: AROMATIC COMPOUNDS

4.1 INTRODUCTION
WORKSHEET 4.1

1. How many pi electron, ᴨ electrons are contained in each molecule?

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)

4.2 BENZENE DERIVATIVES

WORKSHEET 4.2

1. Give the IUPAC name for each compound.

a) Br b) c) CHCH3
CH2CH2CH3 CH3

d) CH3
e) C CH3

CH3

38

EXTRA EXERCISE MODULE CHAPTER 4 2020/2021

f) O g) OH h)

C CH3 F

COOH
Br

WORKSHEET 4.3

Draw a structure corresponding to each name

1. o-dichlorobenzene 2. m-diethylbenzene 3. p-bromochlorobenzene

4. 1,4-dinitrobenzene 5. 1,2-benzenediol 6. 1,4-diaminobenzene

7. 3-nitrobenzoic acid 8. m-bromoaniline 9. p-bromotoluene

10. 2-phenyl-1-butene 11. 3-phenylcyclohexanol 12. 2-methyl-3-phenyl-1-
butanol

39

EXTRA EXERCISE MODULE CHAPTER 4 2020/2021

WORKSHEET 4.4
Draw and name all the isomeric dichlorobenzenes (molecular formula C6H4Cl2)

4.3 CHEMICAL PROPERTIES
WORKSHEET 4.5
Show the products of these reactions

a) CH CH2
Br2, CH2Cl2

b)
H2
Pd

c)
HBr

WORKSHEET 4.6
Draw the product formed when benzene is treated with the following alkyl halide in the
presence of AlCl3?

a) CH3CH2Cl
b) 2-chlorobutane
c) chlorocyclopentane

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EXTRA EXERCISE MODULE CHAPTER 4 2020/2021

WORKSHEET 4.7
Draw the product formed when benzene is treated with the following acyl chloride in the
presence of AlCl3?

O
a) CH3 CH2 C Cl
b) O

C Cl

c) CH3O
CH3 C C Cl
CH3
O

d)
C Cl

WORKSHEET 4.8
Outline the synthesis for the following reactions:

a) nitrobenzene from benzene

b) chlorobenzene from benzene

c) bromobenzene from benzene

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EXTRA EXERCISE MODULE CHAPTER 4 2020/2021

MINDMAP (REACTIONS IN AROMATIC COMPOUNDS)

WORKSHEET 4.9

Based on the following reactions;

O A
CH3

E Cl2 FeCl3

CH3Cl Br2 B
FeBr3
D

AlCl3

conc.HNO3 50 - 55 °C

conc. H2SO4

C

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

b) What is the suitable reagent used for E?

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

d) What is the type of reaction involved for the formation of product B?

MULTIPLE CHOICE QUESTIONS
WORKSHEET 4.10
1. Which statement about benzene is incorrect?

A. The C6 ring is planar.
B. Each C atom is sp2 hybridized
C. The reactivity of the benzene reflects the presence of carbon-carbon double bonds.
D. The C–C π-bonding is delocalized.

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EXTRA EXERCISE MODULE CHAPTER 4 2020/2021

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. Identify the correct statement which is related to aromatic hydrocarbon?
A. It has only sigma bonds
B. It has only pi bonds
C. It has a sigma and two pi bonds
D. It has sigma and delocalized pi bond

4. Select the incorrect option.
A. The aromatic hydrocarbon has a pleasant aroma (smell)
B. Some of the aromatic compounds are ring-shaped
C. Aromatic hydrocarbon can be either mono or polycyclic
D. Benzene is the simplest aromatic hydrocarbon

5. Which of the following statements is incorrect: aromatic compounds...
A. are planar
B. have 4n ᴨ-electrons
C. are cyclic
D. are completely conjugated

6. Name the following compound
OH

A. Benzene

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EXTRA EXERCISE MODULE CHAPTER 4 2020/2021

B. phenyl
C. Benzol
D. phenol

7. What is the molecular formula of Benzene?
A. C6H12
B. C6H10
C. C6H6
D. C8H8

8. What is the accepted current view of the model for bonding in benzene?
A. Delocalised model
B. Resonance structure
C. Kekule structure
D. Arrhenius structure

9. Which mechanism an aromatic compounds react by?
A. Electrophilic addition
B. Nucleophilic addition
C. Electrophilic substitution
D. Nucleophilic substitution

10. What is the other name of aromatic hydrocarbons?
A. Alkenes
B. Arenes
C. Alkynes
D. Alkanes

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EXTRA EXERCISE MODULE CHAPTER 4 2020/2021

11. Which is the correct drawing of 2-bromonitrobenzene?
A. NO2

Br
B. NO2

Br

C. NO2

Br
D. NO2

Br Br

12. Which is the correct drawing of 1,3-dibromo-2-nitrobenzene?
A. NO2

Br
B. NO2

Br

C. NO2

Br

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EXTRA EXERCISE MODULE CHAPTER 4 2020/2021

D. NO2
Br Br

13. OH

Cl
What is the name of this compound?
A. 2-chlorophenol
B. 4-chlorophenol
C. chlorophenol
D. m-chlorophenol

14. What will be the product formed when benzene reacts with Br2 in CCl4 medium?
A. bromobenzene
B. 1,2-dibromobenzene
C. 1,2-dibromocyclohexane
D. None of the above

15. How would you synthesis the following reaction?
? NO2

A. conc. HNO3 + conc. H2SO4
B. HCl + CO + AlCl3
C. Cl2, FeCl3
D. NH3

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EXTRA EXERCISE MODULE CHAPTER 4 2020/2021

16. Which of the following act as catalysis in the nitration of benzene?
A. conc. HNO3
B. conc. HCl
C. conc. H2SO4
D. dilute H2SO4

17. The reaction in which benzene reacts with alkyl halide in the presence of a lewis acid as a catalyst
to produce alkylbenzene is known as ___________
A. Nitration
B. Halogenation
C. Friedel-Crafts Acylation
D. Friedel-Crafts Alkylation

18. The following are the reaction involved in benzene except
A. Nitration
B. Halogenation
C. hydrogenation
D. Freidel-Craft Alkylation

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