ORGANIC CHEMISTRY (LL) W/WILEYPLUS NEXT
ORGANIC CHEMISTRY (LL) W/WILEYPLUS NEXT
12th Edition
ISBN: 9781119664635
Author: Solomons
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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Give reasons: (i) C—Cl bond length in chlorobenzene is shorter than C—Cl bond length in CH3—Cl.(ii) The dipole moment of chlorobenzene is lower than that of cyclohexyl chloride.(iii) SN1 reactions are accompanied by racemization in optically active alkyl halides
(a) Cyclohexa-1,3-diene can be converted into a tetrasubstituted haloalkane when reacted with bromine in ether. Write a balanced chemical equation for the reaction that occurs and state the expected observation.  (b) Compound A and B are alkenes with the same molecular formula C5H10. Compound A is a branched-chain alkene while compound B is a straight-chain alkene. The reaction between compound A with hydrogen bromide produces major product C which is optically active.  (i) Draw TWO (2) possible structures for compound B. (ii) Outline the mechanism for the reaction between compound A with hydrogen bromide to form major product C.  (iii) Name the product formed when compound A undergoes bromination reaction.
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