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CONFIDENTIAL EH/JUNE2018/CHE143/TEST2

PART A (15 MARKS)

QUESTION 1

a) Give the IUPAC names of the following compounds:

i)

ii)

(3 marks)

b) Classify the following compounds below as primary (1o), secondary (2o) or tertiary (3o)
alcohol.

i)

ii)

(3 marks)
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CONFIDENTIAL EH/JUNE2018/CHE143/TEST2

c) Arrange the compounds in 1(b) by decreasing order of boiling point.

1-pentanol , 4,4-dimethylpentan-2-ol, 2,2,3-trimethylpentan-3-ol

Decreasing order of boiling point

Reason:

The more the branching in a compound, the more spherical is its shape and the less its
surface. So tertiary alcohol has smaller surface area than primary alcohol. The smaller the
surface area, the less is London force having the same molecular weight. The less the London
force, the boiling point will decrease. This is because of, to change the molecule from liquid
state to gaseous state, less heat energy required. So, the boiling point of 3o alcohol is less
than that of 1o alcohol.

Moreover, this may also be explained by the fact that steric hindrance prevents the formation
of strong hydrogen bonding between molecules of branched alcohol. That’s why, 3o alcohol
cannot form the strong hydrogen bonding compare to the 1o alcohol. With increasing the
probability of the formation of strong hydrogen bond will increase the boiling point. Hence, 1o
alcohol boils at higher temperature compare to 3o alcohol.

(1 mark)
d) Refer to the following scheme below.

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CONFIDENTIAL EH/JUNE2018/CHE143/TEST2

QUESTION 2

a) i)

ii)

b) i)

ii)

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CONFIDENTIAL EH/JUNE2018/CHE143/TEST2

c) i) Reduction acetic acid to ethanal

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