Organic Chemistry
Organic Chemistry
8th Edition
ISBN: 9781305580350
Author: William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher: Cengage Learning
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Chapter 3.3, Problem 3.2P

Assign priorities to the groups in each set.

  1. (a) —CH2OH and —CH2CH2OH
  2. (b) —CH2OH and —CH=CH2
  3. (c) —CH2OH and —C(CH3)3
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(A)Menthol, used to flavor various foods and tobacco, is the most stable stereoisomer of 2-isopropyl-5-methylcyclohexanol. Draw its most stable conformation. Is the hydroxyl group cis or trans to the isopropyl group? To the methyl group? (b) Neomenthol is a stereoisomer of menthol. That is, it has the same constitution but differs in the arrangement of its atoms in space. Neomenthol is the second most stable stereoisomer of 2-isopropyl-5methylcyclohexanol; it is less stable than menthol but more stable than any other stereoisomer. Write the structure of neomenthol in its most stable conformation.
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For each highlighted carbon identify what type of orbitals it has and how many of each. Then predict the approximate bond angle about each highlighted carbon.

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