Organic Chemistry: Structure and Function
Organic Chemistry: Structure and Function
8th Edition
ISBN: 9781319079451
Author: K. Peter C. Vollhardt, Neil E. Schore
Publisher: W. H. Freeman
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Chapter 4, Problem 59P
Interpretation Introduction

Interpretation:The correct positioned substituent in the cyclohexane derivative should be chosen.

Concept introduction:In chair form, all the C—C—C bond angle are 109.5 ° . Since this is ideal tetrahedral angle so there is no angular strain in chair form. The staggered C—H bond further allows for no amount of torsional strain. There are two kinds of hydrogens in cyclohexane namely axial and equatorial indicated as follows:

  Organic Chemistry: Structure and Function, Chapter 4, Problem 59P

Usually the stable conformations have bulkier groups such as isopropyl, tert-butyl placed equatorially while small atoms such as hydroxyl hydrogen present axial. This is table as the bulkier group tends to have repulsive interaction with axial hydrogen via 1,3-diaxial interactions.

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