Organic Chemistry: Structure and Function
Organic Chemistry: Structure and Function
8th Edition
ISBN: 9781319079451
Author: K. Peter C. Vollhardt, Neil E. Schore
Publisher: W. H. Freeman
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Chapter 3, Problem 25P
Interpretation Introduction

Interpretation:Potential-energy/reaction-coordinate diagrams for the two propagation steps of the radical bromination of benzene should be sketched.

Concept introduction: Analogous to hydrocarbons the benzene can also undergo initiation to generate bromine radicals; propagation of radicals formed and finally termination. This sequence can be outlined as follows:

Step1: Initiation via homolytic cleavage of BrBr bond: Br2 initiates the reaction; undergoes homolysis and forms bromine radical atom. Energy for homolytic cleavage is provided by the heat or ultraviolet light.

  Organic Chemistry: Structure and Function, Chapter 3, Problem 25P , additional homework tip  1

Step2: Propagation: In first of the propagation steps, bromine radical from step 1 abstracts hydrogen radical from C6H6 as follows:

  Organic Chemistry: Structure and Function, Chapter 3, Problem 25P , additional homework tip  2

In subsequent propagation step,phenyl radical abstracts Br· radical from another Br2 , and liberates bromobenzene and new bromine radical.

  Organic Chemistry: Structure and Function, Chapter 3, Problem 25P , additional homework tip  3

Step3: Termination: Bromine radicals generated in propagation steps get quenched upon combination with one another illustrated as follows:

  Organic Chemistry: Structure and Function, Chapter 3, Problem 25P , additional homework tip  4

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