Organic Chemistry (9th Edition)
Organic Chemistry (9th Edition)
9th Edition
ISBN: 9780321971371
Author: Leroy G. Wade, Jan W. Simek
Publisher: PEARSON
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Chapter 26.2B, Problem 26.4P
Interpretation Introduction

Interpretation: The reason for addition of isobutylene molecules do not occurs at the opposite position in its cationic polymerisation with BF3 is to be explained.

Concept Introduction: Cationic polymerisation is the polymerisation in which the reaction of formation of polymer proceeds through the formation of cation. The formation of polymer in this type of polymerisation totally depends upon the stability of cation formed in the polymerisation reaction.

To determine: The reason for no isobutyl molecules adds to opposite orientation in the polymerisation reaction.

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Define the Mechanism - Cationic Polymerization of CH2=CHZ ?
The mechanism given for cationic polymerization of isobutylene  shows that all the monomer molecules add with the same orientation, giving a polymerwith methyl groups on alternate carbon atoms of the chain. Explain why no isobutylene molecules add with the opposite orientation.
Styrene can autoinitiate free radical polymerization and form polystyrene in the absence of an initiator. At temperatures >100 °C, radicals form due to homolysis of the T bond in the vinyl group. In the study of this reaction, researchers have found 1,2-diphenylcyclobutane in samples of heated styrene. The following mechanism for the formation of 1,2-diphenylcyclobutane has been proposed: Step 1: Homolysis of the vinyl T bond in a styrene molecule Step 2: Homolysis of the vinyl T bond in a second styrene molecule Step 3: Tail-to-tail addition of the radicals from Steps 1 and 2 Step 4: Radical coupling of the diradical formed in Step 3 (a) Use curved arrow notation to show the steps in this mechanism. (b) Are the steps in this mechanism consistent with those for free radical polymerization? (c) Why is the use of an initiator such as benzoyl peroxide more efficient in the synthesis of polystyrene than autoinitiated polymerization?
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