Test 2 FHSC1124 ORGANIC CHEMISTRY 1.

5 Hours

Q1. (a) Give the IUPAC name for the following compounds.

(i)

(2 marks)

(ii)

(2 marks)

(iii)

(2 marks)

(b) Draw the structures of the following compounds

(i) 4,4-Dibromobut-2-ene-2,3-diol (2 marks)

(ii) 3-Benzyl-4-iodohexa-1,3,5-triene (2 marks)

(iii) 2,4,6-Trinitrobenzoic acid (2 marks)

(c) Name a chemical test to differentiate the following compounds. State the
observation for both compounds.

1-Phenylhexan-1-ol and 4-phenylhexan-2-ol

(3 marks)
[Total : 15 marks]

This question paper consists of 3 questions on 3 printed pages.

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FHSC1124 ORGANIC CHEMISTRY

Q2. (a) Complete the following equations by drawing the product(s) formed.

(i)

H3CH2C C Cl
NO2 A + HCl
AlCl3

(2 marks)

(ii)

O
OH
+ B + C
OH
(3 marks)

(b) Based on the reaction scheme below, draw the structures for compound D, E, F, G and
H.

HCl D KCN
(minor product) E + KCl
ether reflux
Mg ether LiAlH4
ether
G
O F
H2O, H3O+
H3C C CH3

H + Mg(OH)Cl
(10 marks)

[Total : 15 marks]

This question paper consists of 3 questions on 3 printed pages.

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FHSC1124 ORGANIC CHEMISTRY

Q3. (a) Based on the reaction scheme below, draw the structures for compounds A, B,
C, D and E.

Cl

SOCl2 OH KCN in ethanol

A D
Reflux
FeCl3 1. LiAlH4 / ether
2. H3O+

B + C
(white fumes) E
(9 marks)

(b) Compound F is an acyclic alcohol and it is optically active. Upon heating with
concentrated H2SO4, the major compound G with a molecular formula of C5H10
is formed. Compound G exhibits geometric isomerism. Besides, compound F
also reacts with sodium metal to form compound H and liberates hydrogen gas.
Draw the structures of compounds F, G and H. (6 marks)
[Total : 15 marks]

Q4. (a) (i) Give the IUPAC name for the following compound.

(2 marks)

(ii) Draw the structure of 2,4-dihydroxybenzenesulphonic acid. (2 marks)

(b) Compound A reacts with nitric acid in the presence of catalyst B to produce
3-nitroaniline.

(i) Name compound A and catalyst B. (3 marks)

(ii) State the type of mechanism involved in the production of 3-nitroaniline.

(1 mark)

(iii) Outline the mechanism stated in Q1. (b) (ii). (7 marks)

[Total: 15 marks]
This question paper consists of 3 questions on 3 printed pages.
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FHSC1124 ORGANIC CHEMISTRY

Q5. (a) Table 3.1 shows the relative rates of SN2 reactions with respect to the class of
alkyl halides.

Class of alkyl halides Compound Relative rate

Methyl Chloromethane 2500
1° Chloroethane 50
2° R 1
3° 2-Chloro-2-methylbutane S
Table 3.1

(i) Explain the relationship between the relative rates of reaction with
respect to the class of alkyl halide. (3 marks)

(ii) Give an example for compound R, which is a four - carbon alkyl

chloride. (2 marks)

(iii) Predict the value of S. Explain your answer. (2 marks)

(b) Compound Z reacts with a mixture of concentrated nitric acid and concentrated
sulphuric acid to produce 3-nitrobenzaldehyde.

(i) Identify compound Z. (2 marks)

(ii) Outline the mechanism of the reaction. (6 marks)

[Total: 15 marks]

Q6. (a) (i) Give the IUPAC name for the following compound.

Br
Br

Br (2 marks)

(ii) Draw the structure of 1-fluoro-3,4-dimethylhexane. (2 marks)

(b) 2-Bromo-2-methylbutane is hydrolysed in water via unimolecular substitution

reaction to produce an alcohol. Outline the mechanism. (6 marks)

(c) Show the synthesis pathway for the conversion below. State the reagent(s) and
condition(s) involved.

This question paper consists of 3 questions on 3 printed pages.

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FHSC1124 ORGANIC CHEMISTRY

HO
HO
(5 marks)
[Total : 15 marks]

Q7. (a) (i) Give the IUPAC name for the following compound.

HO

OH (2 marks)

(ii) Draw the structure of m-fluorophenol. (2 marks)

(b) 2-Chlorobutan-2-ol is more acidic than 2-methylbutan-2-ol. Explain why.

(7 marks)

(c) Suggest a chemical test to distinguish A from B. State the reagent(s), condition
and expected observation(s). (4 marks)

OH H

H3CH2C C CH3 H3CH2C C CH3

OH

A B
[Total : 15 marks]

This question paper consists of 3 questions on 3 printed pages.