ASSIGNMENT OF

EPHEDRINE

Submitted To:

Mam Sara Musaddiq

Submitted By:

Umm-e-Farwa

Roll. No 43

BS Chemistry (Biochem-Special)

8th Semester

THE WOMEN UNIVERSITY MULTAN

1.1 Ephedrine

Ephedrine is an alkaloid and its molecular formula is𝐶10 𝐻15 𝑁𝑂.

1) Acetylation of ephedrine gave two acetyl derivatives which implies that ephedrine may
have two hydroxyl groups or two amine groups or one hydroxyl and one amine group. The
molecular formula showed that there is only one nitrogen and one oxygen so third
assumption is correct.
2) The nitrogen can be in the form of secondary amine or primary amine as tertiary amine
cannot give acetylation reaction. To confirm the nature of nitrogen ephedrine was treated
with nitrous acid which gave nitroso derivative which implied that ephedrine contains
secondary amine group.
3) Upon vigorous oxidation ephedrine gave benzoic acid which showed that ephedrine
contains one benzene ring and one side chain.
COOH

KMnO4
Ephedrine

This test implies that ephedrine structure can be as following.

C4H10NO

4) On mild oxidation compound gave methyl amine and propiophenone.

 O

C CH2CH3

HCL + CH3NH2
Ephedrine

The liberation of methyl amine indicates the presence of N-methyl group and formation of
ketone indicates the presence of secondary alcohol.
Thus the considering all the previous interpretation ephedrine structure can be as following.

OH OH
H
CH C CH3 CH C CH3
H2
NHCH3
NHCH3

Both structures can undergo all previous reactions so further confirmation was done by
Hoffman’s degradation method.

OH
O
H
CH C CH3 CH C CH3
H
NHCH3
 OH O

CH C CH2
CH C CH3 H2
H2

NHCH3

As ephedrine actually gives 1-2 epoxide so structure one was considered correct.
5) This structure was further confirmed by stereo chemical evidence. Ephedrine in fact show
optical activity. Structure one and two both possess 2 and 1 chiral center respectively. So
hydroxyl group was replace by hydrogen and optical activity of ephedrine was measured.
Ephedrine still showed optical activity which is only possible for structure 1.

Thus structure of ephedrine is as following.

OH
H
CH C CH3

NHCH3