UNIVERSITY OF ZULULAND FACULTY OF SCIENCE AND

AGRICULTURE
DEPARTMENT OF CHEMISTRY
SCHM 212 (ORGANIC CHEMISTRY): TEST 1 memorandum
Examiner: Dr SE Mavundla
August 2015

Date: 07

Duration: 1 hr
Marks: 40

Total

Answer all questions

Question 1: Multiple choice (5 marks)

1.1.1. Under what reaction conditions does the electrophilic chlorination of
aromatic compounds usually occur?

1.2.

1.3.

A.
B.
C.
D.

NaCl, CH3OH
Cl2, AlCl3
Cl2, CCl4
NaCl, H2O

E.

Cl 2 , H 2 O

Which of the following species is attacked by benzene in the

electrophilic nitration reaction?
A.

HNO3

B.

NO2+

C.

NO2

D.

N3 -

E.

NO+

In electrophilic aromatic substitution reactions the hydroxyl group is

an o, p-director because:
A.

it donates electron density to the ring by resonance and

stabilizes the ortho and para sigma complexes.

B.

it donates electron density to the ring by induction and

stabilizes the ortho and para sigma complexes.

C.

it donates electron density to the ring by resonance and

destabilizes the meta sigma complex.

1.4.

1.5.

D.

it withdraws electron density from the ring by induction and

destabilizes the meta sigma complex.

E.

it donates electron density to the ring by induction and

destabilizes the meta sigma complex.

The nitration of anisole:

A.

proceeds at the same rate as the nitration of benzene and

yields predominantly the meta product.

B.

proceeds more rapidly than the nitration of benzene and

yields predominantly the ortho, para products.

C.

proceeds more slowly than the nitration of benzene and

yields predominantly the ortho, para products.

D.

proceeds more slowly than the nitration of benzene and yields

predominantly the meta product.

E.

proceeds more rapidly than the nitration of benzene and

yields predominantly the meta product.

Which of the following is the strongest activating group in

electrophilic aromatic substitution reactions?
A. -OCH3
B. -N(CH3)2
C. -CH2CH3
D. -NO2
E. -CO2CH3

Question 2 (9 marks)
2.1.

Draw the structure of the following compounds. (1 mark each)

(i) Aniline

(ii) Anisole

NH2

OCH3

(iii) meta-chloro-isobutylbenzene
methylphenol

(iv) 3-chloro-5-

OH

H3C

Cl

2.2.

Cl

Name the following compounds (1 mark each):

COOH

Cl

(i)

as benzene

(ii)

Br

OH

(ii)
(i)

1-chloro-4-isobutylbenzene, (ii) 4-bromo-benzoic acid, (iii) 2, 6dimethylphenol or 2,6-dimethyl-1-hydroxybenzene

2.3. State whether the following compounds are aromatic or not (1 mark
each).

(i). not

Question 3

(ii).

not

(11 marks)

Give product(s) or reagents (where applicable) needed for the following

reactions:

OH

OH

OH
HO3S

SO3, H2SO4
SO3H

(a).

Cl

COOH

H3C

Cl2
COOH

FeCl3

(b).
NO2

CH3Cl
AlCl3

(c).

NO REACTION

Na or Mg
NH3, Alcohol
(d).

(e).
COOH

KMnO4, OHHeat, H2O

(f).
O

Cl

Zn(Hg)

AlCl3

HCl

Cl

CH3

Cl2
AlCl3

(g).

O
Cl

NO2

NO2

CH3COCl
AlCl3
COCH3

(h).

Question 4 (16 marks)

4.1.

Draw the four resonance structures of the sigma complex

intermediate in the reaction of anisole with HNO3/H2SO4 to yield
ortho-nitroanisole. (4)

O
O

NO2

NO2

NO2
NO2

4.2.

Explain why the treatment of benzene with 1-chloropropane in the

presence of AlCl3 yield more isopropylbenzene than propylbenzene.
(5)
secondary carbocation
more stable than
primary

primary carbocation less stable and

leads to hydride shift
AlCl3

Cl

4.3.

Provide a series of synthetic steps by which meta-nitrobutylbenzene

can be prepared from benzene. (5)
O

Cl

O
O2N

O2 N

reduction

Alternatively
6

NO2

NO2

NO2

Acylation

Reduction
Zn(Hg)
COCH2CH2CH3

4.4.

CH2CH2CH2CH3

Explain why the reaction of benzene with Br2/FeBr3 is faster than the
reaction of nitrobenzene with Br2/FeBr3. (2)

Nitro group deactivate the ring by withdrawing electrons from the

benzene ring.