To explain the stereochemistry which is observed when radical halogenations generally yield a mixture of stereoisomers. When a Br atom is adjacent to the site of hydrogen abstraction, however, the reaction is stereospecific. A detailed mechanism for the reaction is to be determined. Concept introduction: The stereochemistry at the chiral center is inverted as soon as H atom is abstracted to form the cyclic radical. Attack of Br 2 occurs from the opposite side of the attached bromine which inverts the stereochemical configuration.

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Chapter 25, Problem 25.71P

Interpretation Introduction

Interpretation:

To explain the stereochemistry which is observed when radical halogenations generally yield a mixture of stereoisomers. When a Br atom is adjacent to the site of hydrogen abstraction, however, the reaction is stereospecific. A detailed mechanism for the reaction is to be determined.

Concept introduction:

The stereochemistry at the chiral center is inverted as soon as H atom is abstracted to form the cyclic radical. Attack of Br₂ occurs from the opposite side of the attached bromine which inverts the stereochemical configuration.

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