Answered: OH H i) H CO₂H, B H A ii) Diels-Alder…

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OH H i) H CO₂H, B H A ii) Diels-Alder chiral, optically pure C

Organic Chemistry: A Guided Inquiry

2nd Edition

ISBN:9780618974122

Author:Andrei Straumanis

Publisher:Andrei Straumanis

Chapter15: Radical Reactions

Section: Chapter Questions

Problem 14E

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Question

The reaction was intended to proceed via a Fischer esterification of the chiral, optically pure alcohol A with the carboxylic acid B, followed by an intramolecular Diels-Alder cycloaddition to yield the product C. Unexpectedly, the product C turned out to be a racemic mixture of enantiomers, exhibiting no optical activity. This outcome indicated that the Fischer esterification did not proceed as anticipated.

draw a rxn mechanism to show why ester was formed instead and the optical activity was lost? What could the scientists have done to prevent ester formation?

OH
H
i) H CO₂H, B
H
A
ii) Diels-Alder
chiral, optically pure
C

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