Tutorial - Benzene and Its Derivatives (A) (Editted)

ANSWER SCHEME(TUTORIAL) SK O25
6.0: BENZENE AND ITS DERIVATIVES

SECTION A
1. Which of the following is NOT a number of Hückel’s rule?
A. 2
B. 6
C. 14
D. 16
2. A hydrocarbon with six carbon atoms is said to be aromatic if

A. It is a cyclic compound.
B. The compound has more than one C=C bond.
C. All of the atoms in the molecule are on the same plane.
D. It is cyclic, planar and has six delocalised π electrons.
3. Name the given structure below
A. p-bromopropylbenzene
B. m-bromopropylbenzene
C. m-bromoethylbenzene
D. o-bromopropylbenzene
4. Choose the correct statement for the reaction below.
A. The electrophile is H2SO4.

B. H2SO4 is a Brønsted–Lowry base.
C. Benzene undergoes electrophilic addition reaction.
Unit Kimia, KMKt 2021/2022 36

D. Benzene undergoes electrophilic aromatic substitution.
5. What is the function of Lewis acid in halogenation of benzene?
A. It initiates the formation of halogen radical.
B. It increases the polarity of halogen molecule.
C. It produces an electrophile.
D. It produces a nucleophile.
6. The product of the reaction below is
A. C.
B. D.
7. What is/are the possible name(s) for the following compound?
I 1,3-dihydroxybenzene
II Benzene-1,3-diol
III 3-hydroxyphenol
A. I only

B. I and II
C. II and III
D. I, II and III
8. This can be a halide in the Friedel-Crafts alkylation reaction
A. chloroethene
B. chlorobenzene
C. bromobenzene
D. isopropyl chloride
9.
Choose the correct statement about the above reaction.

I. X and Y are Cl2 and uv light respectively.
II. The reaction is a free radical substitution reaction.
III. The reaction is an electrophilic substitution reaction.
A. I only
B. I and II
C. II and III
D. I, II and III
10. Although some of the early scientists believed that benzene is a triene (a
compound with three C=C bonds), which of the following observations prove
otherwise?
A. Benzene does not decolourise bromine colour
B. Benzene absorbs hydrogen gas to form cyclohexane
C. Benzene is insoluble in water but dissolves in ether
D. Benzene burns with a yellow, sooty flame

SECTION B
1. (a) What is an aromatic compound?

An aromatic compound is a cyclic, planar, completely conjugated
compound and obey Huckel’s rule.
(b) Cyclopropenyl cation is the simplest aromatic compound.
i. Draw two other possible resonance structures of this cation.
ii. Describe the aromaticity of cyclopropenyl cation.
● Cyclopropenyl cation contains 2π electrons that obeys Hückel’s

rule with n=0.
● All carbon atoms are sp2 hybridised and the π electrons are
delocalised in the unhybridised p orbitals.
● Cyclopropenyl cation possesses a cyclic conjugated system with
sp2 hybridisation.
2. (a) Name the compounds below according to the IUPAC nomenclature.

i.
2-phenylbutanoic acid
ii.
p-bromoiodobenzene@ 1-bromo-4-iodobenzene
iii.
m-fluoroacetophenone @ 3-fluoroacetophenone
iv.
o-cyclopentylaniline @ 2-cyclopentylaniline
(b) Write the structural formulae for each of the following compounds.
i. 1,3,5-trinitrobenzene

ii. m-isopropylphenol
iii. 4-chloro-2,dinitrotoluene
iv. Benzaldehyde

3. Complete the following reaction equations and name the compound A, B, and C
(a)
(b)
(c)
A: bromobenzene
B: 3-nitrobenzoic acid @ m-nitrobenzoic acid
C: isopropylbenzene
4. Give the complete equation for the chlorination reaction of benzene and
cyclohexene. State the type of reaction involves.

5. According to the following reactions.
i.
ii.
(a) State the electrophile involved in (i).
(b) State the catalyst catalyst used in (i) and (ii). What is the function of the
catalyst in the reaction?
(i) AlCl 3 (ii) H2SO4

to produce an electrophile.
(c) Write the reaction mechanism in (ii)
Step 1: Formation of electrophile (nitronium ion)

Step 2: Formation of arenium ion
Step 3: Loss of H+
6. Based on the following reaction scheme below;

(a) Write the structural formula of E and F and specify reagent I.
E:
F:
Reagent I:
(b) Write the mechanism for the formation of E.
Step 1: Formation of electrophile

Step 2: Formation of arenium ion
Step 3: Loss of H+
7. Suggest a chemical test to differentiate cyclohexene from benzene. Give the

equation involved and its observations.
Test Bromine test
Reagent& Reagent: Br2 in CCl4
Condition Condition: in the dark @ under sunlight

Compound cycohexene benzene
Observation Reddish brown colour of Reddish brown colour of

bromine solution bromine solution remain
decolourised. unchanged
Equation
8. (a) When an aromatic hydrocarbon G, C8H10 is heated with acidified

potassium manganate (VII), a compound H, C7H6O2 is obtained.
i. Draw the structural formula of G.
ii. Write an equation to show the reaction in (a).

(b) J is an isomer of G. When J is heated with the reagent in (a), a

compound K, C8H6O4 is obtained.
i. Draw the structural formula of J.
ii. Write an equation to show the reaction in (b).
9. Compound L has formula, C7H7Cl
(a) Draw all possible structures of L

(b) Which of the isomer is formed from free radical substitution of toluene?
10. Outline the synthesis of the following compounds from benzene
(a) Benzoic acid
(b) 1-phenylethanol


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ANSWER SCHEME(TUTORIAL) SK O25

6.0: BENZENE AND ITS DERIVATIVES

2. A hydrocarbon with six carbon atoms is said to be aromatic if

3. Name the given structure below

4. Choose the correct statement for the reaction below.

A. The electrophile is H2SO4.

Unit Kimia, KMKt 2021/2022 36

6. The product of the reaction below is

7. What is/are the possible name(s) for the following compound?

Unit Kimia, KMKt 2021/2022 37

Choose the correct statement about the above reaction.

Unit Kimia, KMKt 2021/2022 37

1. (a) What is an aromatic compound?

(b) Cyclopropenyl cation is the simplest aromatic compound.

i. Draw two other possible resonance structures of this cation.

ii. Describe the aromaticity of cyclopropenyl cation.

● Cyclopropenyl cation contains 2π electrons that obeys Hückel’s

2. (a) Name the compounds below according to the IUPAC nomenclature.

Unit Kimia, KMKt 2021/2022 38

Unit Kimia, KMKt 2021/2022 37

Unit Kimia, KMKt 2021/2022 37

B: 3-nitrobenzoic acid @ m-nitrobenzoic acid

Unit Kimia, KMKt 2021/2022 36

(a) State the electrophile involved in (i).

(i) AlCl 3 (ii) H2SO4

(c) Write the reaction mechanism in (ii)

Step 1: Formation of electrophile (nitronium ion)

Unit Kimia, KMKt 2021/2022 37

Step 2: Formation of arenium ion

6. Based on the following reaction scheme below;

Unit Kimia, KMKt 2021/2022 38

(a) Write the structural formula of E and F and specify reagent I.

(b) Write the mechanism for the formation of E.

Step 1: Formation of electrophile

Unit Kimia, KMKt 2021/2022 39

Step 2: Formation of arenium ion

7. Suggest a chemical test to differentiate cyclohexene from benzene. Give the

Test Bromine test

Reagent& Reagent: Br2 in CCl4

Condition Condition: in the dark @ under sunlight

Unit Kimia, KMKt 2021/2022 40

Observation Reddish brown colour of Reddish brown colour of

8. (a) When an aromatic hydrocarbon G, C8H10 is heated with acidified

i. Draw the structural formula of G.

ii. Write an equation to show the reaction in (a).

Unit Kimia, KMKt 2021/2022 41

(b) J is an isomer of G. When J is heated with the reagent in (a), a

i. Draw the structural formula of J.

ii. Write an equation to show the reaction in (b).

9. Compound L has formula, C7H7Cl

(a) Draw all possible structures of L

Unit Kimia, KMKt 2021/2022 42

10. Outline the synthesis of the following compounds from benzene

(a) Benzoic acid

Unit Kimia, KMKt 2021/2022 43

Unit Kimia, KMKt 2021/2022 44

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