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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Question
Chapter 5.1, Problem 5.3E
(a)
Interpretation Introduction
Interpretation:The natural products indicated should be identified as either chiral or achiral.
Concept introduction:
The enantiomers are identical chemical compounds that have a mirror-image relationship to each other while diastereomers do not hold mirror image relationships. The former are chiral and optically active while the latter can be chiral or achiral.
Four kinds of symmetry elements that may be present are tabulated as follows:
Presence of any symmetry element makes molecule achiral and optically inactive.
(b)
Interpretation Introduction
Interpretation: The three molecules that represent enantiomers of
Concept introduction: The enantiomers are identical chemical compounds that have a mirror-image relationship to each other while diastereomers do not hold mirror image relationships. The former are chiral and optically active while the latter can be chiral or achiral.
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There are four dimethylcyclopropane isomers.
(a) Write three-dimensional formulas for these isomers.
(b) Which of the isomers are chiral?
(c) If a mixture consisting of 1 mol of each of these isomers were subjected to simple gas
chromatography, how many fractions would be obtained and which compounds would each
fraction contain?
(d) How many of these fractions would be optically active?
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page 10 of 17
4.(a). Draw the structures of (i) cis-1,4-Dibromocyclohexane and (ii) trans-1,4-
Dibromocyclohexane.
4(b). Draw the most stable conformers of (i) cis-1,4-Dibromocyclohexane and (ii)
trans-1,4-Dibromocyclohexane.
4(c)Which is more stable? (i) cis-1,4-Dibromocyclohexane or (ii) trans-1,4-
Dibromolcyclohexane. Explain the reason for your choice.
12. Natural (2)-menthol, the essential oil primarily responsible for the flavor and aroma of peppermint, is
the IR,25,5R-stereoisomer. (a) Identify (2)-menthol from the structures you drew for Problem 50, part
(b). (b) Another of the naturally occurring diastereomers of menthol is (1)-isomenthol, the 1S 2R5R-
stereoisomer. Identify (1)-isomenthol among your structures. (c) A third is (1)-neomenthol, the
15.25,SR-compound. Find (1)-neomenthol among your structures. (d) Based on your understanding of
the conformations of substituted cyclohexanes (Section 4-4), what is the stability order (from most
stable to least) for the three diastereomers, menthol, isomenthol, and neomenthol?
Chapter 5 Solutions
Organic Chemistry: Structure and Function
Ch. 5.1 - Prob. 5.3ECh. 5.1 - Prob. 5.4ECh. 5.1 - Prob. 5.5ECh. 5.2 - Prob. 5.6ECh. 5.2 - Prob. 5.8TIYCh. 5.3 - Prob. 5.9ECh. 5.3 - Prob. 5.11TIYCh. 5.3 - Prob. 5.12ECh. 5.4 - Prob. 5.13ECh. 5.4 - Prob. 5.14E
Ch. 5.4 - Prob. 5.16TIYCh. 5.4 - Prob. 5.17ECh. 5.5 - Prob. 5.18ECh. 5.5 - Prob. 5.19ECh. 5.5 - Prob. 5.20ECh. 5.6 - Prob. 5.21ECh. 5.6 - Prob. 5.22ECh. 5.6 - Prob. 5.23ECh. 5.7 - Prob. 5.24ECh. 5.7 - Prob. 5.26TIYCh. 5.7 - Prob. 5.27ECh. 5 - Prob. 5.1ECh. 5 - Prob. 5.2ECh. 5 - Prob. 30PCh. 5 - Prob. 31PCh. 5 - Prob. 32PCh. 5 - Prob. 33PCh. 5 - Prob. 34PCh. 5 - Prob. 35PCh. 5 - Prob. 36PCh. 5 - Prob. 37PCh. 5 - Prob. 38PCh. 5 - Prob. 39PCh. 5 - Prob. 40PCh. 5 - Prob. 41PCh. 5 - Prob. 42PCh. 5 - Prob. 43PCh. 5 - Prob. 44PCh. 5 - Prob. 45PCh. 5 - Prob. 46PCh. 5 - Prob. 47PCh. 5 - Prob. 48PCh. 5 - Prob. 49PCh. 5 - Prob. 50PCh. 5 - Prob. 51PCh. 5 - Prob. 52PCh. 5 - Prob. 53PCh. 5 - Prob. 54PCh. 5 - Prob. 55PCh. 5 - Prob. 56PCh. 5 - Prob. 57PCh. 5 - Prob. 58PCh. 5 - Prob. 59PCh. 5 - Prob. 60PCh. 5 - Prob. 61PCh. 5 - Prob. 62PCh. 5 - Prob. 63PCh. 5 - Prob. 64PCh. 5 - Prob. 65PCh. 5 - Prob. 66PCh. 5 - Prob. 67PCh. 5 - Prob. 68PCh. 5 - Prob. 69PCh. 5 - Prob. 70PCh. 5 - Prob. 71P
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