CHM556

Mac-Jun 2017
Test 2

Name: UiTM ID: Group:

Answer ALL questions. Total: 30 marks.

Question 1
Propose the starting ketone and enone required to synthesize the following compound via Robinson
annulation. In addition, draw the structure of the intermediate formed via Michael addition reaction.

Michael Robinson
addition annulation
Ketone Enone Intermediate

(6 marks)
Question 2
a) Benzaldehyde and acetophenone will undergo Aldol condensation and later dehydration forming an
α,β-unsaturated ketone (also known as chalcone), X, as follows.

1. Aldol condensation
Chalcone, X
2. Dehydration

Benzaldehyde Acetophenone

i) Draw a complete mechanism for the formation of chalcone X. (7 marks)

ii) Provide a suitable reagent for the transformation. (1 mark)
iii) If 3-nitrobenzaldehyde is used instead of benzaldehyde in the above reaction, would you
expect the Aldol condensation reaction to be more favoured or less favoured to occur?
Explain your answer. (3 marks)

b) With regards to the following reaction scheme, answer all questions below.

CrO3
B

1. SOCl2
? 2. CH3OH

H3O+
Transesterification
C
product

i) Provide the appropriate reagent for the transformation of benzaldehyde to its hydroxyl
analogue (A) and draw the structures of compounds B and C. (5 marks)
ii) Suggest the structure of the intermediate formed during the conversion of B to C. (1 mark)
iii) The reaction between compound A and compound C is a transesterification reaction.
Propose the mechanism for the reaction and draw the structure of the transesterification
product. (5 marks)
iv) Why does the transesterification reaction need an acidic condition? (2 marks)