© The Hong Kong Polytechnic University

The Hong Kong Polytechnic University

Department of Applied Biology and Chemical Technology

FINAL EXAMINATION: ABCT2742 ORGANIC CHEMISTRY I

Subject: Organic Chemistry I Subject Code: ABCT2742

Year : Programme: 12352/12447/12454

Class :

Session : 2016/17 Semester 2

Date : 28 April 2017

Time Allowed : 3 hours Time: 15:15 – 18:15

This question paper has 7 printed pages including the cover page.

Instructions to Candidates:

 This paper contains 10 questions

 Answer ALL questions using the separate Answer Books provided.

 You MUST return this question paper and the answer books to the invigilators after the examination

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 Examination and Have Your Devices Kept underneath Your Seat

Name :

Student no :
 © The Hong Kong Polytechnic University

Complete All Questions using Answer Books (100 marks)

Section A (30 %) Answer All Questions in the Blue Answer Book

Q1. Explain the difference in acidity for the following pairs:

a. Phenol (pKa = 9.9) and ethanol (pKa = 16)

b. Trifluoroacetic acid (pKa = -0.3) and acetic acid (pKa = 4.75)

(6 marks)

Q2. Indicate the type of hybridization of atoms highlighted in the following structures:

a. b. c.

(4 marks)

Q3. Sketch 1H NMR spectra for the following molecules:

a. b.

(8 marks)

Page 2 of 7
 © The Hong Kong Polytechnic University

Q4. The following NMR spectra belong to two ketone isomers with a formula of C 5H10O. Deduce their
structures and explain your answer.

Isomer 1 Singlet Doublet

3H 6H

Septet
1H

Isomer 1

Page 3 of 7
 © The Hong Kong Polytechnic University

Singlet
Isomer 2 3H

Triplet
3H

Triplet
Sextet
2H
2H

Isomer 2

(12 marks)

- END OF SECTION A –

Page 4 of 7
 © The Hong Kong Polytechnic University

Section B (70 %) Answer All Questions in the Pink Answer Book

Q1. Regarding the following reaction with compound A:

H2SO4, H2O


A

a. Provide the IUPAC name of compound A.

b. Provide the major product of the above reaction, and show the reaction mechanism.

c. Provide the major product when compound A reacts with BH3 in THF, and then treated with H2O2 in
water.

(10 marks)

Q2. Regarding the following reaction with compound A:

1. PBr3
B
OH 2. NaOCH3
A

a. Determine the stereochemistry of the chiral center in product B, and show the reaction mechanism.

b. Describe the method for the reaction with compound A to provide the enantiomer of product B, and
show the reaction mechanism.

(10 marks)

Q3. In the reaction of methylcyclohexane and Br2 under light (h):

a. Show the structure of the major product, and the reaction mechanism.

b. Provide the reagents for converting methylcyclohexane to 1-bromo-2-methylcyclohexane, and the

reaction mechanism.

(10 marks)

Page 5 of 7
 © The Hong Kong Polytechnic University

Q4. Complete the following tree of reactions by providing the reagents (a) - (e).

CH3
Br CH3
Br
Br
(c) (b)

CH3 CH3 CH3

(d) (a)

Br
Br
(e)

CH3
OH
Br

(10 marks)

Q5. Provide the reagents to complete the following syntheses a, b, c.

a.

Steps
HC CH

b.

Steps
HC CH

c.

OH
Steps
HC CH
Br

(15 marks)

Page 6 of 7
 © The Hong Kong Polytechnic University

Q6. (I) a. The bulky group remains at the equatorial position because of steric effect. In the presence of
NaOH in acetone, which compound (A or B) can undergo elimination? Explain why.

Br Br

A B

b. In the presence of methanol, determine the major products of C and D, and explain why.

Br Br
CH3 CH3

C D

(II) Provide the synthetic route and reaction mechanisms of the following transformation:

Steps H3CO

(15 marks)

- END OF SECTION B-

- END OF PAPER -

Page 7 of 7