© The Hong Kong Polytechnic University

The Hong Kong Polytechnic University

Department of Applied Biology and Chemical Technology

Programme : 12352/12447/12454
Subject : Organic Chemistry I Subject Code : ABCT2742

Year : 2018/19

Session : Semester 2

Date : 27 April 2019

Time Allowed : 3 hours Time : 08:45 – 11:45

This question paper has FOUR printed pages excluding the cover page.

Instructions to Candidates:

 This paper has a total of 11 questions in TWO Sections. Answer ALL questions
 Use Separate answer books for Section A (BLUE) and Section B (PINK)
 Use Black / Blue Ballpoint pen for preparing your answers in the scripts

DO NOT turn over this page until you are told to do so

Keep Away All Scrap Papers
Keep Your Mobile Phone / Laptop Computers Turned Off at All Time During
the Exam and Have Your Devices Kept in Your Bag underneath Your Seat
____________________________________________________________________________
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Section A (Questions 1 – 6): Answer ALL questions (40%)

Write your answers for Section A in the BLUE answer book

1. Draw an orbital picture for acetylene, C2H2. Clearly label each bond type and indicate the type
of orbitals involved in each bond.

(3 marks)
2. (a) Label the acid, conjugate acid, base and conjugate base in the reaction below.

(b) Comment if the reaction stated in 2(a) would take place or not. Explain briefly.
(4
mark
s)

3. Sketch the 1H NMR and 13C NMR (1H-decoupled) spectra of the following compound.

(7 marks)

4. Assign one of the following compounds to which the IR spectrum should correspond. Briefly
explain.
(5
mark
s)

A. B. C.

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5. Assign one of the following compounds to which the following spectrum should correspond
Briefly explain.
(5 marks)

6. Referring to the following 1H NMR, and 13C NMR spectra, elucidate the molecular structure
of the ester compound with formula C6H12O2. Support your answer with explanation.
(16 marks)
1H NMR spectrum

13C NMR spectrum

-End of Section A-

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Section B (Questions 7 – 11): Answer ALL questions (60%)

Write your answers for Section B in the PINK answer book

7. For the following cases (a) and (b), in each case identify the one which is more reactive
toward SN2 reactions. Illustrate your answers using potential energy diagrams.

(a) - - (5 marks)
OMe (methoxide) CCH (acetylide)

(b) 1-bromohexane 1-fluorohexane (5 marks)

8. (a) Treatment of 2-bromopentane with alcoholic potassium hydroxide produced a mixture of

cis- and trans-2-pentenes. Which stereoisomer is likely to be the major product?

Explain your answer with a potential energy diagram. (8 marks)

(b) If 2-bromopentane is now heated with alkoxide 8.1, give the structure of the major alkene
product. Rationalize your answer using a potential energy diagram.

O Na

alkoxide 8.1

(7 marks)

9. The following reactions (a) – (c) failed to give to the desired targets 9.1, 9.2 and 9.3.

In each case, explain briefly why the transformations fail. Propose a method or synthetic
route for effective syntheses of the target molecules.

(a)
NaOH Ph O OH
H 3C H 3C
Ph
9.1

(b) OH
1) H 2SO 4
2) H 2O
9.2

(c)
Br 2 Br
hn
9.3
(15 marks)

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10. Alkene 10.1 reacts with bromine in ethanol to give two diastereomeric bromohydrin products
according to the following equation:

(a) Give the structures of the products. (2 marks)

(b) Propose the reaction mechanism to account for the bromohydrins formation. Based on your
mechanism, predict the major diastereomeric product. Explain your answer.
(8 marks)

11. Draw the products of each reaction and indicate the stereochemistry where applicable.

(a)

(b)

(c)

(10 marks)

-End of Section B-

-END OF PAPER-