Answered: cinnamoylcocaine Н,о Ph o"Ph Ph NaOCH,…

Chemistry

10th Edition

ISBN:9781305957404

Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste

Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste

Chapter1: Chemical Foundations

Section: Chapter Questions

Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...

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Question

Cinnamoylcocaine, a natural product that occurs in coca leaves, can be converted to cocaine by the following reaction sequence. Identify the structure of cinnamoylcocaine, as well as intermediates

cinnamoylcocaine
Н,о
Ph o"Ph
Ph
NaOCH,
C19H23NO.
CH3I
cocaine
HO.
снон

Expert Solution

Step 1

The given reaction is shown below.

In order to obtain the compounds X and Y, the retrosynthetic method has to be followed.

Cocaine is obtained by the methylation of compound Y, so the compound Y is a secondary amine. The possible structure of compound Y is shown below.

Step 2

The compound Y is obtained by the reaction of compound X with benzoic anhydride. So as to get compound Y from compound X and benzoic anhydride, the compound X should have an alcohol group. The possible structure of X is shown below.

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