Organic Chemistry: Principles and Mechanisms (Second Edition)
Organic Chemistry: Principles and Mechanisms (Second Edition)
2nd Edition
ISBN: 9780393663556
Author: Joel Karty
Publisher: W. W. Norton & Company
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Chapter 11, Problem 11.55P
Interpretation Introduction

Interpretation:

The detailed mechanism that illustrates the initiation and addition of the first two monomers in the given polymerization reaction is to be drawn.

Concept introduction:

Polymerization reactions start with the generation of a reactive species from a monomer molecule. The reactive species may be a radical or a carbocation. This reactive species then adds to another molecule of the monomer to form a dimer. At the same time, a radical or a carbocation is generated on the added molecule, which can continue the addition reaction.

In the case of acid-catalyzed alkene polymerization, a proton transfer from the acid to a molecule of alkene generates a carbocation reactive species. This in turn acts as an electrophile and adds to the double bond from another monomer molecule, generating a second, dimeric carbocation. This carbocation will then propagate the polymerization reaction.

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Organic Chemistry: Principles and Mechanisms (Second Edition)

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