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 21P
Interpretation Introduction

Interpretation: The chain-initiating and chain-propagating steps showing the formation of the products in the given reaction are to given.

Concept Introduction:

A free radical halogenation reaction is a type of reaction in which thereplacement of hydrogen atom with a bromine atom in the moleculetakes place in the presence of UV light. It is a type of a halogenation reaction.

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.

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The reaction of 3-methylene-1-cyclohexene and HBr yields the four products shown in the attachment. Which two are formed at high temperatures and which two are formed at low temperatures? Why? Why is 1-bromo-3-methylenecyclohexane not formed?
A benzene ring alters the reactivity of a neighboring group in the so-called “benzylic” position, similarly to how a double bond alters the reactivity of groups in the “allylic” position. Benzylic cations, anions, and radicals are all more stable than simple alkyl intermediates. a) Use resonance structures to show the delocalization of the positive charge, negative charge, and unpaired electron of the benzyl cation, anion, and radical.
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Organic Chemistry

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