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 42P
Interpretation Introduction

Interpretation:The manner inhibition of radical chlorination of methane is possible when radical inhibitors such as I2 are added should be explained.

Concept introduction:The mechanism for monochlorination comprises of three stages illustrated as follows:

Step 1- Initiation via homolytic cleavage of ClCl bond: Cl2 initiates the reaction; undergoes homolysis to yield chlorine radicals. Energy for homolytic cleavage is provided by the heat or ultraviolet light.

  Organic Chemistry: Structure and Function, Chapter 3, Problem 42P , additional homework tip  1

Step 2: Propagation: In the first of the propagation steps, Cl·radical generated from step 1 abstracts hydrogen radical from methane as follows:

  Organic Chemistry: Structure and Function, Chapter 3, Problem 42P , additional homework tip  2

In subsequent propagation step,chloromethyl radical abstracts Cl· radical from another Cl2 , and liberates dichloromethane and new Cl· radical.

  Organic Chemistry: Structure and Function, Chapter 3, Problem 42P , additional homework tip  3

Step3: Termination: Radicals generated in propagation steps get quenched upon the combination with one another. Thus termination steps are essentially the radical− radical combination illustrated as follows:

  Organic Chemistry: Structure and Function, Chapter 3, Problem 42P , additional homework tip  4

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