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 24P
Interpretation Introduction

Interpretation: Mechanism for monobromination of methane that includes initiation, propagation and termination steps should be written.The value of ΔH° involved in each propagation step and the reaction as a whole should be calculated. The reaction should be thermodynamically compared with other bromination reaction of alkanes.

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

It is summarized in the illustration below:

  Organic Chemistry: Structure and Function, Chapter 3, Problem 24P

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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