BSc/MSci Course Unit Examination

Main Examination Period 2017

CHE102B FUNDAMENTALS OF ORGANIC CHEMISTRY (Semester B)

Duration: 2 h 00

YOU ARE NOT PERMITTED TO START READING THIS QUESTION PAPER UNTIL INSTRUCTED TO
DO SO BY AN INVIGILATOR.

Answer ALL the questions in Section A and ONE question only from Section B. The total of marks available
on the paper is 80, with Section A worth 55 marks and Section B worth 25 marks.
A detailed marking scheme is provided for your guidance.
A data booklet is also provided, which may contain data and formulae relevant to the questions on this
examination paper. Approved molecular models are permitted in this examination. All molecular model sets
must be disassembled at the start of the examination.

CALCULATORS ARE PERMITTED IN THIS EXAMINATION. PLEASE STATE ON YOUR ANSWER

BOOK THE NAME AND TYPE OF MACHINE USED.

COMPLETE ALL ROUGH WORKINGS IN THE ANSWER BOOK AND CROSS THROUGH ANY WORK
WHICH IS NOT TO BE ASSESSED.

IMPORTANT NOTE: THE ACADEMIC REGULATIONS STATE THAT POSSESSION OF

UNAUTHORISED MATERIAL AT ANY TIME WHEN A STUDENT IS UNDER EXAMINATION
CONDITIONS IS AN ASSESSMENT OFFENCE AND CAN LEAD TO EXPULSION FROM THE
COLLEGE. PLEASE CHECK NOW TO ENSURE YOU DO NOT HAVE ANY NOTES IN YOUR
POSSESSION. IF YOU HAVE ANY THEN PLEASE RAISE YOUR HAND AND GIVE THEM TO AN
INVIGILATOR IMMEDIATELY.
PLEASE BE AWARE THAT IF YOU ARE FOUND TO HAVE HIDDEN UNAUTHORISED MATERIAL
ELSEWHERE, INCLUDING TOILETS AND CLOAKROOMS IT WILL BE TREATED AS BEING FOUND
IN YOUR POSSESSION. UNAUTHORISED MATERIAL FOUND ON YOUR MOBILE PHONE OR OTHER
ELECTRONIC DEVICE WILL BE CONSIDERED THE SAME AS BEING IN POSSESSION OF PAPER
NOTES. MOBILE PHONES CAUSING A DISRUPTION IS ALSO AN ASSESSMENT OFFENCE.

EXAM PAPERS CANNOT BE REMOVED FROM THE EXAM ROOM.

Examiners: Dr X Cambeiro, Dr G Chianello and Dr N Lebrasseur

© Queen Mary University of London, 2017

Page 2 of 4 CHE102B (2017)

SECTION A

1. Answer all the multiple-choice questions in the supplementary book using the multiple-choice
examination answer sheet provided. [25 marks]
DO NOT TAKE THE QUESTION BOOK FROM THE EXAMINATION ROOM.

2. Answer all parts.

(a) Consider the following synthetic sequence for the preparation of n-propylbenzene (4).

(i) Provide suitable reagent(s) to carry out each step. [4 marks]

(ii) Provide a curved arrow mechanism for step a. [4 marks]
(iii) The more direct route to n-propylbenzene (4), shown below, presents two major
drawbacks. Using curved arrow mechanisms to support your arguments, highlight
what those drawbacks are. [7 marks]

(b) With reference to the following reaction scheme.

(i) Identify compound A and provide a curved arrow mechanism to account for its
formation. [3 marks]

(ii) State if the transformation of 6 to A is an oxidation or a reduction. [1 mark]

(iii) Identify compound B and provide a curved arrow mechanism to account for its
formation. [5 marks]

(c) Identify the carboxylic acid and alcohol that could be used to prepare each of the
following esters. [2 marks]

Question 2 continues overleaf

CHE102B (2017) Page 3 of 4

(d) Identify the reagents C and D that could be used to prepare the following compound.
[2 marks]

(e) Identify the products E and F of the following reaction. [2 marks]

SECTION B

3. Answer all parts.

(a) With reference to the following reaction scheme:

(i) Suggest suitable reagent(s) for carrying for steps a, b and c. [4 marks]
(ii) Provide a curved arrow mechanism for step b. [3 marks]
(iii) Suggest a structure for compound G. A curved arrow mechanism is not required.
[2 marks]
(iv) Provide a curved arrow mechanism for the transformation of G to 11. [7 marks]
(v) Suggest a structure for compound H. A curved arrow mechanism is not required.
[2 marks]

(b) Identify compound I and provide a curved arrow mechanism for its formation. Account
for the expected regioselectivity by providing an analysis of the Wheland intermediate.
[7 marks]
Page 4 of 4 CHE102B (2017)

4. Answer all parts.

(a) With reference to the following reaction scheme:

(i) Identify compound J. [1 mark]

(ii) Suggest suitable reagent(s) for carrying out steps a and b. Curved arrow mechanisms
are not required. [4 marks]
(iii) Propose a curved arrow mechanism for step b. [4 marks]
(iv) Identify compound K and propose a curved arrow mechanism to account for its
formation. [4 marks]
(v) Name the functional group(s) present in molecule 15. [1 mark]
(vi) Suggest suitable reagent(s) for carrying out step c and propose a curved arrow
mechanism for this transformation. [6 marks]

(b) Identify product L and provide a curved arrow mechanism to account for its formation.
[5 marks]

End of Paper