CHM557

20234 [OCTOBER 2023 – FEBRUARY 2024]

TEST 2

Name :
UiTM ID :
Group :

Answer all questions. Total: 30 marks

Question 1
Compounds such as β-keto esters can be synthesized via intramolecular chemical
reaction of diesters with base. This reaction also known as Dieckmann
condensation. Based on this statement consider the scheme below.

OCH3
Base
Compound T
OCH3

O
Compound S

a) Predict the chemical structure for compound T.

(2 marks)
b) State a base that being used for this reaction.
(1 mark)
c) Show a stepwise mechanism for the conversion of compound S to T.
(5 marks)

Question 2
Robinson annulation is the reaction that involved of Michael Addition and Aldol
Condensation. Consider the following scheme.

O O
Aldol
Michael Addition D
A + B Condensation

Compound C
a) Predict the chemical structure of A, B and D.
(6 marks)
b) Write the plausible mechanism for the formation of compound D from C.
(4 marks)

Question 3
Consider the following scheme

a) State the reagents A, B and C.

(3 marks)
b) Draw the chemical structure for Compound W and X.
(4 marks)
c) Redraw back the structure of dimethyl malonate and identify the most acidic α-
hydrogen.
(1 mark)
Question 4
The following scheme is referred to

HOH2C O OH
H CH2OH
H OH
OHH

beta-D-fructose

a) Draw a fisher projection structure for β-D-fructose.

(1 mark)
b) D-psicose are epimer for D-fructose at carbon 3. Illustrate the fisher projection
structure for D-psicose.
(1 mark)
c) Predict the chemical structure(s) when β-D-fructose react with an excess of acetic
anhydride in pyridine and an excess of methyl iodide.
(2 marks)