KOLEJ UNIVERSITI TUNKU ABDUL RAHMAN

CENTRE FOR PRE-UNIVERSITY STUDIES

ACADEMIC YEAR 2020/2021

DECEMBER EXAMINATION

FPCH1034 ORGANIC CHEMISTRY

FRIDAY, 18 DECEMBER 2020 TIME: 2.30 PM – 4.30 PM (2 HOURS)

FOUNDATION IN SCIENCE
FOUNDATION IN ENGINEERING

Instructions to candidates:

1. Answer ALL questions in the format/ template requested or provided.

2. Include your FULL NAME, STUDENT ID, PROGRAMME OF STUDY and
SEMESTER in your answer submission.
3. This is an open book final online assessment; but you MUST NOT receive any help
whatsoever from any other person.
4. Read all the questions carefully and understand what you are being asked to answer.
5. Marks are awarded for your own (original) analysis. Therefore, use the time and
information to build well-constructed, concise, accurate and thoughtful answers with
supporting explanations and justifications.
6. You must submit your answer within the time frame allowed for this online
assessment. The deadline for the submission of your answers is half an hour from the
end time of this online assessment.
7. Penalty as below WILL BE IMPOSED on students who submit their answers late as
follows:
i) The final marks of this online assessment will be reduced by 10 marks for answer
scripts that are submitted within 30 minutes after the deadline for the submission of
answers for this online assessment.
ii) The final marks of this online assessment will be downgraded to zero (0) mark for
any answer scripts that are submitted after one hour from the end time of this online
assessment.
8. Any late submission after the stipulated time frame or no submission, are deemed to
be failure of the online assessment. [Note: For candidates facing problems to submit
the online assessment, please email to [email protected] within 48 hours of the
online assessment to apply for "I" indicator under Extenuating Mitigating
Circumstances (EMC) situation. Attach your email with supporting documents and
EMC form which can be obtained from your student intranet.]
9. Students are required to complete the declaration section before submission of your
answer.

This question paper consists of 5 questions in 6 printed pages.

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FPCH1034 ORGANIC CHEMISTRY

STUDENT’S DECLARATION OF ORIGINALITY

By submitting this online assessment, I declare that this submitted work is free from all forms
of plagiarism and for all intents and purposes is my own properly derived work. I understand
that I have to bear the consequences if I fail to do so.

This question paper consists of 5 questions in 6 printed pages.

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FPCH1034 ORGANIC CHEMISTRY

Answer ALL questions.

Question 1
a) This question is about the structural isomers.
(i) Give the structures of a pair of positional isomers with the formula C4H8. (2 marks)

(ii) Give the structures of a pair of chain isomers with the formula C4H8, that do not exhibit
stereoisomerism. (2 marks)

(iii) Give the structures of a pair of functional group isomer with the formula C4H8.
(2 marks)

b) But-1-ene does not show stereoisomerism. However, but-1-ene reacts with HCl to form a
mixture of structural isomers X and Y.

(i) Identify the empirical formula of but-1-ene. (1 mark)

(ii) Explain the meaning of the term stereoisomers. (2 marks)

(iii) Name two different types of stereoisomers. (2 marks)

(iv) Give two reasons why but-1-ene does not show stereoisomerism. (2 marks)

(v) Draw the structural formulae and give the names of X and Y. (4 marks)

(vi) Name the type of stereoisomerism shown by X. (1 mark)

(vii)Use the conventional representation to draw the two stereoisomers of X. (2 marks)

[Total: 20 marks]

Question 2
a) Alkane is a saturated hydrocarbon.
(i) Define the term hydrocarbon. (1 mark)
(ii) What is the general formula of chain alkane? (1 mark)
(iii) List two physical properties of alkane. (2 marks)
b) Compounds A, B and C are isomers with molecular formula C5H12.
CH3CH2CH2CH2CH3 (CH3)2CHCH2CH3 (CH3)3CCH3
A B C
(i) Draw the displayed formula of compound A, B and C. (3 marks)
(ii) Name the compound A, B and C. (3 marks)
(iii) Arrange boiling point of A, B and C in ascending order. (3 marks)
This question paper consists of 5 questions in 6 printed pages.
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FPCH1034 ORGANIC CHEMISTRY

Question 2 (continued)
(iv) Explain the effect of branching to the boiling point of the above molecules. (3 marks)
c) Cyclohexanol and phenol are both fairly soluble in water.

(i) Explain why these two compounds are more soluble in water than cyclohexane and
benzene. (2 marks)
(ii) Explain why phenol is more acidic than cyclohexanol. (2 marks)
[Total: 20 marks]
Question 3
a) Some reactions based on 1-bromobutane, CH3(CH2)3Br, are shown.

Give the reagent(s) and condition(s) for each of the reaction above. (12 marks)

b) Complete the diagram below to show the SN2 mechanism of reaction 1. R represents the
CH3(CH2)2 group. Include all necessary charges, dipoles, lone pairs and curly arrows.

(3 marks)

c) 2-bromo-2-methylpropane is treated with the same reagents as in reaction 1.

(i) Suggest the structural formulae and name of the organic product formed. (2 marks)

(ii) Identify the mechanism for this reaction. (1 mark)

(iii) Explain why this reaction proceeds via a different mechanism from that of reaction 1.
(2 marks)
[Total: 20 marks]

This question paper consists of 5 questions in 6 printed pages.

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FPCH1034 ORGANIC CHEMISTRY

Question 4
a) The compound trans -4-hydroxy-2-nonenal (HNE) is thought to lead to infections of the
lung when cigarettes are smoked.

(i) Identify three functional groups which are present in the HNE molecule. (3 marks)

(ii) For each functional group, state a suitable reagent and the observation you would make
to confirm the presence of the stated functional groups in (a)(i). (6 marks)

b) Identify the organic product formed in the following reactions:

(i)
Room temperature

(1 mark)
NaOH
(ii) CH3COCH3 + HCN (1 mark)
10 - 20°C
(iii)

+ cold
(1 mark)

c) Write a balanced equation of the following reactions:

(i) ethanoic acid and magnesium carbonate (2 marks)

(ii) complete combustion of propane (2 marks)

(iii) ethyl ethanoate and dilute sodium hydroxide (2 marks)

(iv) phenol and sodium (2 marks)

[Total: 20 marks]

Question 5
a) Define the term polymerisation. (2 marks)

b) (i) Name two different types of polymerisation and give one example of polymer for each
type of polymerisation. (4 marks)

(ii) State two characteristic differences for each type of polymerisation. (4 marks)

This question paper consists of 5 questions in 6 printed pages.

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FPCH1034 ORGANIC CHEMISTRY

Question 5 (continued)

c)

Polymer A Polymer B

(i) Give the structure of monomer(s) that produce polymer A. (2 marks)

(ii) Give the structure of monomer(s) that produce polymer B. (1 mark)

(iii) Explain why polymer B will cause environmental disposal problem. (1 mark)

(iv) Suggest a possible solution to solve the above problem. (1 mark)

d) Alanine is one of the amino acids for making proteins.

(i) What is a protein? (1 mark)

(ii) Using alanine as an example, draw a diagram to show how dipeptide are formed from
amino acids. Label the bond. (2 marks)

(iii) Show two repeat units of the peptides formed in (d)(ii). (1 mark)

(iv) Draw the zwitterionic structure of alanine. (1 mark)

[Total: 20 marks]

This question paper consists of 5 questions in 6 printed pages.