Organic Chemistry
Organic Chemistry
12th Edition
ISBN: 9781118875766
Author: T. W. Graham Solomons, Craig B. Fryhle, Scott A. Snyder
Publisher: WILEY
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Chapter 10, Problem 17PP
Interpretation Introduction

Interpretation:

Ethene, vinyl chloride, and acrylonitrile do not undergo cationic polymerization while isobutylene gives the same, is to be explained.

Concept Introduction:

Alkenes also undergo polymerization reaction when treated with strong acids. The growing chains in acid catalyzed polymerization are cations, rather than radicals.

A cation is an electron deficient species and its stability order is as follows:

1o<2o<3o

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A hydrocarbon (X), with the molecular formula: C8H14 is reduced in presence of sodium and liquid ammonia to give the only product (Y) with the molecular formula: C8H16. Compounds X and Y both resulting 2,5-dimethylhexane when treated with hydrogen and platinum catalyst (H2/Pt). As a result of the oxidative cleavage of compound Y (by using KMnO4 / H2SO4), a single carboxylic acid derivative with C4H8O2 molecular formula is formed. Again, as a result of the reaction of  Y with perbenzoic acid, the chiral compound C8H14O is observed, but the reaction of compound Y with bromine gives the achiral C8H14Br2 as the product.
Please draw out the structures of compound A, B, C, D and E. The formula of Compound A is C5H6. Compound A react with 2 equivalent of Br2 to produce product B; Compound A was oxidized with KMN04 to give two carboxylic acids C and D. Compound A can undergo Diels-Alder reaction with maleic anhydride to produce compound E.
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