Victoria Junior College

2012 JC2 H2 Chemistry Enrichment Paper 4

Alkenes and Arenes (Tutors Copy)
Name:
CT Group:

Marks:
/20
Duration: 30 min

Answer all the questions.

1
The following scheme shows some reaction pathways starting from 2-methylbut-2ene.

C5H11Br
C

HBr

CH3CH C(CH3)2
A

cold, dilute
alkaline KMnO4

concentrated
H2SO4
H2O
heat

C5H12O
E

C5H12SO4
D
(a)

C5H12 O2
B

Give the displayed formulae of the organic compounds B to E.

B

[4]

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

H H
H H C H
H C C C C H
H H O H H
O S O H
O

H H

H H
H H C H

H H
H H C H

H C C C C H
H H Br H H

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

(b)

Write a balanced equation showing how A reacts with cold dilute

alkaline potassium manganate (VII).
[1]
CH3CH=C(CH3)2 + [O] + H2O CH3CH(OH)C(OH)(CH3)2

(c)

When A reacts with bromine in the presence of concentrated aqueous

sodium nitrate, the product contains the following compound.

ONO2
CH3CHC(CH3)2
Br
Draw the intermediate formed in this reaction.
+
CH3CHC(CH3)2

[1]

Br
2

The molecular formula, C4H8, applies to three structurally isomeric alkenes.

(a) Write the structural formulae for these three alkenes.
[3]
CH2=CHCH2CH3, CH3CH=CHCH3, (CH3)2C=CH2
(b)

One of these alkenes can be obtained by the dehydration of the

alcohol of the structural formula below:
CH3 CH CH2OH

CH3
Name the alkene.

[1]

2-methylpropene
(c)

Give the reagents and conditions needed for the dehydration in (b). [1]
Excess concentrated H2SO4, 170oC

A student proposed the following scheme to show the interconversion

between benzene and some of its derivatives.
CH3

CO2H

CH3

III

NO2

IIb

IV
CH2Cl

Ib

IIa

NO2
Ia

(a)

Give the reagents and conditions required for the following steps:
Step
IIa
IIb
III
IV

(b)

[3]

Reagents and conditions

CH3Cl, anhydrous FeCl3, room temp.
Conc. HNO3, conc. H2SO4, 30oC
Acidified KMnO4 (aq), heat
Cl2, uv light, excess methylbenzene

Which of the two pathways I or II should be used to synthesize 2nitromethylbenzene? Explain briefly.
[2]

Pathway II.
NO2 is a meta-director, pathway I would result in 3
nitromethylbenzene.
As CH3 is an ortho, para-director, pathway II would result in 2nitromethylbenzene as one of the main products.
(c)

Describe the mechanism for the reaction IIb.

Mechanism of the reaction is electrophilic substitution.

Methylbenzene, due to pi electrons in the benzene ring, is
electron-rich and hence susceptible to electrophilic attack.
A strong electrophile, NO2+, is first generated:
2H2SO4 + HNO3 NO2+ + H3O+ + 2HSO4Electrophilic attack then ensues:

[3]

CH3

CH3
H

NO2+

NO2

CH3

CH3

NO2

H
+

NO2

HSO4-

H2SO4

H2SO4, being a catalyst, is regenerated at the end of the reaction.

[Total 4, max 3]