Organic Chemistry Study Guide and Solutions Manual, Books a la Carte Edition (8th Edition)
Organic Chemistry Study Guide and Solutions Manual, Books a la Carte Edition (8th Edition)
8th Edition
ISBN: 9780134649771
Author: Paula Yurkanis Bruice
Publisher: PEARSON
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Chapter 12, Problem 36P
Interpretation Introduction

Interpretation:

The major product of the given reaction should be identified.

Concept introduction:

Radical or free radical: unpaired valence electron of an atom, molecule, or ion is called as radical.

Bond strength is depends on the formation of the radical, if the radical is involving in resonance which is weakest bond strength.

Bromination of Allylic Carbons:

Organic Chemistry Study Guide and Solutions Manual, Books a la Carte Edition (8th Edition), Chapter 12, Problem 36P , additional homework tip  1

N-bromosuccinimide (NBS) is used for the allylic bromination through radical reaction. bromination of allylic carbon requires low concentration of bromine and low concentration of hydrobromic acid. If high concentration of bromine and high concentration of hydrobromic acid which leads to the formation of bromination in the double bond.

Organic Chemistry Study Guide and Solutions Manual, Books a la Carte Edition (8th Edition), Chapter 12, Problem 36P , additional homework tip  2

Bromination reaction starts with the homolytic cleavage of N-Br bond in N-bromosuccinimide (NBS) which creates bromine radical to initiate the radical bromination reaction.

NBS bromine radical removes the allylic hydrogen which forms hydrogen bromide and allylic radical in the first propagation step, the allylic radical is stabilized by the double bond in ring. This allylic radical reaction with bromine molecule and forms allylic bromide in the second propagation step which are shown above.

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Chapter 12 Solutions

Organic Chemistry Study Guide and Solutions Manual, Books a la Carte Edition (8th Edition)

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