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 8PP
Interpretation Introduction

Interpretation: An alkane, on reaction with chlorine, gives a single monochloro substitution product. Based on this information, the structure of the alkane is to be deduced.

Concept introduction:

Higher alkanes, on chlorination, give a mixture of products as chlorine is unselective.

If all the hydrogen atoms are homotopic, the halogenation of the alkane or the cycloalkane gives a single monochloro substitution product.

The hydrogen atoms that, on replacement by some other group, yield the same compound are known as homotopic hydrogens.

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Develop syntheses for the following compounds. As starting materials, you may use cyclopentanol, alcohols containing no more than four carbon atoms, and any common reagents and solvents. (a) trans-cyclopentane-1,2-diol (b) 1-chloro-1-ethylcyclopentane
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