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 3.5, Problem 3.6E

(a)

Interpretation Introduction

Interpretation: The reason behind hydrogen abstraction by chlorine rather than bromine atoms even when equimolar amount of each is present should be explained.

Concept introduction: The monochlorination performed with ultraviolet light proceeds via radical chain mechanism. Chlorine transforms CH4 into chloromethane as the major halogenated product with variety of side products due to various possibility of chain termination. The chloromethane formed can undergo another cycle of radical mechanism to yield dichloromethane

The fundamental radical chain mechanism is summarized in the illustration below:

  Organic Chemistry: Structure and Function, Chapter 3.5, Problem 3.6E

(b)

Interpretation Introduction

Interpretation: The bond enthalpies involved in radical halogenation carried out with tert-butylhypochlorite should be calculated.

Concept introduction: The monochlorination performed with ultraviolet light proceeds via radical chain mechanism. Chlorine transforms CH4 into chloromethane as the major halogenated product with variety of side products due to various possibility of chain termination.

The formula to calculate ΔH° from bond dissociation of reactants and products is as follows:

  ΔH°=Sum of DH° of bonds brokenSum of DH° of bonds formed

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