CHM096 FOUNDATION CHEMISTRY II (MARCH 2013)

ORGANIC CHEMISTRY (SET 1)

Name: ______________________________________________________________
Student Number: _____________________

CH3

CH3

Tutorial Class:_______________

OH

CH3 CH3 CH3

2,3,4-trimethyl-pentan-2-ol

HCl/Ether
C Minor
KOH/Ethanol
B
D Major

H3O+

KMnO4, H3O+

E
F

2,3,4-trimethyl-pentan-2 ol was treated with HCl in ether to obtain compound B. Then, B is

further treated with KOH in ethanol (CH3CH2O-K+) to form two products, in which one of them is
major compound D. The major compound was separated into two; one of the portions treated
with acid to produce compound E while other portion was treated with hot KMnO4+ in acid
solution to form compound F and G.
a) Draw the structures for compounds B, C, D, E, F and G.
(3 x 6 = 18 marks)
b) Show the reaction mechanism of carbocation formation that lead to the synthesis of
compound C and D.
(2 x 6 = 12 marks)