Requirements for this paper:

Multiple-choice answer Non-programmable calculator: Open book examination?

NO YES NO
sheets:

Graph paper: Laptop:

NO NO

EXAMINATION: Assignment PROGRAMME: BSc

MODULE CODE: NCHM62310 DURATION:

MODULE DESCRIPTION: ORGANIC CHEMISTRY II MARKS: 70

EXAMINER(S): Ms KV PHUNGULA DUE DATE: 25 May

MODERATOR(S): TIME: 23:00

INSTRUCTIONS:
1. Read the instructions for each question very carefully before answering the
question.
2. This paper consists of three questions and three pages including the cover
page.
3. Answer all questions and upload all answers on MOODLE.
4. The use of a non-programmable calculator is allowed; show all your
calculations.
5. The use of laptops, cellphones, pencil and tippex is not allowed.

NCHM62310 (SEMESTER TEST 2022) Page 1/3

 QUESTION 1 (26 Marks)

1.1 What carbonyl compound would you reduce to obtain the following alcohols. (4)

1.2 How would you prepare the following carboxylic acid.

(a) Benzoic acid from bromobenzene (2)
(b) CH3CH2CH2CO2H from CH3CH2CH2Br (2)
1.3 How would you covert N-ethylbenzamide to each of the following products.
(a) Benzoic acid (2)
(b) Benzyl alcohol (2)
1.4 Rank the following compounds in order of increasing acidity.
(a) Benzoic acid, p-methylbenzoic acid, p-chlorobenzoic acid (3)
(b) p-Nitrobenzoic acid, acetic acid, benzoic acid (3)
(c) Fluoroacetic acid, 3-fluoropropanoic acid, iodoacetic acid
1.5. Predict the major monoalkylation products you would expect to obtain from reaction of
the following substances with chloromethane and AlCl3:
(a) Bromobenzene (1)
(b) m-Bromophenol (1)
(c) p-Chloroaniline (1)
(d) 2,4-Dichlorophenol (1)
1.6. Propose syntheses of the following compounds from benzene.
(a) N.N-Dimethylaniline (2)
(b) m-chloroaniline (2)

QUESTION 2 (31 Marks)

2.1 The sulfonation of an aromatic ring with SO 3 and H2SO4 is reversible. That is, heating
benzenesulfonic acid with H2SO4 yields benzene. Show the mechanism of the
desulfonation reaction. What is the electrophile?
(5)
2.2. Explain why the nitration of toluene is considered an orth-para directing deactivator in
electrophilic aromatic substitution. make use of structures and notes. (14)

NCHM62310 (SEMESTER TEST 2022) Page 2/3

2.3 Discuss with the use of structures/reaction equations and notes the acidic properties of
structure below with reference to weakening of the O-H bond and stability of the
carboxylate anion. (7)

2.4 Write the following bases from the weakest base to the strongest base and explain by
using short notes and structures. (5)

QUESTION 3 (13 Marks)

3.1 complete the reaction scheme below. (5)

3.2. complete the reaction also give a full mechanism for the formation of product(s).

(8)

TOTAL [70 MARKS]

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