Organic Chemistry
Organic Chemistry
11th Edition
ISBN: 9781118133576
Author: T. W. Graham Solomons, Craig Fryhle
Publisher: Wiley, John & Sons, Incorporated
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Chapter 10, Problem 11PP
Interpretation Introduction

Interpretation: The allylic monobromo substitution products for the given compounds, the most stable isomeric product based on the double bond, and the resonance hybrid(s) for allylic radicals that are formed in each are to be discussed.

Concept introduction:

Molecules that have one unpaired electron are called free radicals.

A chemical reaction in the presence of a free radical is called a free radical reaction.

Allylic bromination take place in the presence of NBS and peroxide or light. NBS is a good reagent for allylic bromination.

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(3) HI does not undergo free radical addition with 1-butene, even in the presence of a peroxide. Please provide an explanation by analyzing the propagation steps if the same radical reaction occurred with HI. Besides the bond dissociation enthalpies in the appendix, the following approximate bond dissociate enthalpies might be useful to you: ~310 kJ/mol The component of C=C CH3CH₂CH₂CH₂-Br CH3CH₂CH₂CH2-I -290 kJ/mol (C-Br bond) ~235 kJ/mol (C-I bond)
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