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Chem0016c5uc 2021
Chem0016c5uc 2021
Chem0016c5uc 2021
ASSESSMENT : CHEM0016C5UC
PATTERN
LEVEL: : Undergraduate
DATE : 11/05/2021
TIME : 10:00
This paper is suitable for candidates who attended classes for this
module in the following academic year(s):
Year
2020/21
TURN OVER
CHEM0016 page 2 of 6
Candidates should attempt ALL questions. Numbers in square brackets in the right-hand
margin indicate the provisional allocation of marks to the subsections of a question.
Compound D: C8H8O2
max 3040m, 2950s, 2820m, 1695s, 1600m, 1500m cm–1
1
H NMR 3.89 (3H, s)
6.97 (2H, d, J 8.0 Hz)
7.82 (2H, d, J 8.0 Hz)
9.90 (1H, s)
13
C NMR 55.5, 114.3, 130.0*, 132.0*, 162.1, 198.0
*You do not need to assign these signals
Compound E: C16H13NO
max 3040m, 2950m, 2200s, 1620m, 1580m, 1500m cm–1
1
H NMR 3.95 (3H, s)
6.93 (2H, d, J 8.5 Hz)
6.99 (1H, d, J 16.4 Hz)
7.21 (1H, d, J 16.4 Hz)
7.51 (2H, d, J 8.5 Hz)
7.58 (2H, d, J 7.8 Hz)
7.64 (2H, d, J 7.8 Hz)
(i) Give a structure for compound D and assign the IR and NMR data. [4]
(ii) Give a structure for the major isomer of E formed and assign the IR and
1
H NMR data, explaining the coupling constants. [7]
(iii) Provide a mechanism for the formation of E from C and D, explaining the
stereochemical outcome of the reaction. [4]
CHEM0016 page 4 of 6
2. Answer ALL parts.
(a) Propose a structure for A, giving mechanistic details. [5]
O O
O 1. HNO3,
O A
2. C5H5NO3
N
(b) Propose structures for B and C, accounting for their formation and any
regioselectivity. [6]
O
H NH2
O B 1. n-BuLi C
Cl
(c) Propose reagents for D and structures for E and F, giving mechanistic details for
all transformations. [6]
O
D 1. NH2OH, H3O+ 1. Li/NH3, 1 eq t-BuOH
H E F
2. Ac2O C7H5N 2. 1 eq C10H12ClN
Br Cl
O O O
(b) Suggest reagents for the following transformation. More than one step will be
necessary. Rationalize any regioselective steps. [6]
OH NH
(c) Suggest a structure for A. Provide the full mechanisms for steps (ii) and (iii),
rationalizing any chemo-, regio- and/or stereoselective steps. [6]
(i) O3 followed by PPh3
(ii) 1 eq.
PPh3
A
(iii) Excess mCPBA C13H24O3
O O
Cl
CHEM0016 page 6 of 6
4. The synthesis of an alkaloid A is shown below.
END OF PAPER