CHM096 FOUNDATION CHEMISTRY II (MARCH 2013)

ORGANIC CHEMISTRY (SET 3)

Name: ______________________________________________________________
Student Number: _____________________

Tutorial Class:_______________

CH3COOH

CH3COCH2CH3

LiAlH4
H2SO4
C

HBr
E

Reagent x

H2CrO4

D
Aldehyde
Ether
D + F

F
Grignard Reagent

[H2O]

[O]
H

CH3COCH2CH3

Acetic acid CH3COOH is an inexpensive chemical that is used in abundance as starting material
to synthesize many compounds. The above diagram shows the pathway of synthesizing 2butanone CH3COCH2CH3. Answer the following questions according to the diagram.
a) Draw the structures for compounds B, C, D, and E
(4 x 3 = 12 marks)
b) Compound E must be treated with reagent X to produce compound F (Grignards reagent)
What is X?.
(2 marks)
c) Compound D (aldehyde) was reacted with compound F to form compound G and was treated
further to produce compound. This compound H is then oxidized to finally produce 2 butanone
(CH3COCH2CH3). Determine the structures for all compounds F, G, and H
(3 x 3 = 9 marks)
d) Use the reaction mechanism to show how compound B can be converted into compound C
and finally to compound E. Use arrow symbols to indicate the movement of electrons.
(3.5 x 2 = 7 marks)