Introduction to General, Organic and Biochemistry
11th Edition
ISBN: 9781285869759
Author: Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar Torres
Publisher: Cengage Learning
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Chapter 15, Problem 15.31P
Interpretation Introduction
Interpretation:
We have to interpret the chirality and stereoisomers of the given compounds.
Concept Introduction:
A chiral compound contains a chiral carbon atom which must be bonded with four different groups or atoms. The number of stereoisomers can be calculated with the help of formula 2n ; here ‘n’ indicates the number of stereocenters (chiral carbon atoms).
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A chemist synthesized compound X as a racemic mixture. When the ketone group in X was
enzymatically reduced to the corresponding alcohol, a 100% yield was obtained of the product
shown below. Choose the statement that best describes this result.
ОН
enzyme
C;H1
`OCH,CH;
pH 4.0
C3H1
`OCH,CH3
ОН
ÕH
X (racemic)
(100% yield)
One enantiomer of compound X reacts quickly with the enzyme. The other enantiomer of compound X is
unreactive, but rapidly equilibrates with the reactive enantiomer under the reaction conditions.
Since compound X was racemic, it makes sense that only a single product was obtained.
O The product is a meso compound, so either enantiomer of compound X gives the same product.
One enantiomer of compound X reacts quickly with the enzyme, while the other enantiomer of compound X
remains unchanged.
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?
Classify the following pair of compounds as the same compound, enantiomers, diastereomers,
constitutional isomers, or not isomeric. Also, select the correct IUPAC name, including the correct (R) or
(S) designation, for each.
H
÷
||I
The correct IUPAC names are:
||
J
k
CI
same compound
enantiomers
diastereomers
constitutional isomers
not isomeric
Compound I: (2R, 3R)-2,3-dichloropentane, Compound II: (2R, 3S)-2,3-dichloropentane
Compound I: (2S, 3S)-2,3-dichloropentane, Compound II: (2S, 3S)-2,3-dichloropentane
Compound I: (2S, 3R)-2,3-dichloropentane, Compound II: (2S, 3R)-2,3-dichloropentane
Compound I: (2R, 3R)-2,3-dichloropentane, Compound II: (2R, 3R)-2,3-dichloropentane
Chapter 15 Solutions
Introduction to General, Organic and Biochemistry
Ch. 15.1 - Prob. 15.1PCh. 15.2 - Problem 15-2 Assign priorities to the groups in...Ch. 15.2 - Problem 15-3 Assign an R or S configuration to the...Ch. 15.3 - Problem 15-4 3-Amino-2-butanol has two...Ch. 15.3 - Prob. 15.5PCh. 15.3 - Prob. 15.6PCh. 15 - 15-7 Answer true or false. The cis and trans...Ch. 15 - 15-8 What does the term “chiral” mean? Give an...Ch. 15 - 15-9 What does the term “achiral” mean? Give an...Ch. 15 - 15-10 Define the term “stereoisomer.” Name three...
Ch. 15 - 15-11 In what way are constitutional isomers...Ch. 15 - 15-12 Which of the following objects are chiral...Ch. 15 - Prob. 15.13PCh. 15 - Prob. 15.14PCh. 15 - 15-15 Explain why the carbon of a carbonyl group...Ch. 15 - 15-16 Which of the following compounds contain...Ch. 15 - 15-17 Which of the following compounds contain...Ch. 15 - Prob. 15.18PCh. 15 - 15-19 Draw the mirror image for each molecule: OH...Ch. 15 - Prob. 15.20PCh. 15 - 15-21 Answer true or false. For a molecule with...Ch. 15 - Prob. 15.22PCh. 15 - Prob. 15.23PCh. 15 - Prob. 15.24PCh. 15 - Prob. 15.25PCh. 15 - 15-26 For centuries, Chinese herbal medicine has...Ch. 15 - Prob. 15.27PCh. 15 - Prob. 15.28PCh. 15 - Prob. 15.29PCh. 15 - 15-30 (Chemical Connections 15A) What does it mean...Ch. 15 - Prob. 15.31PCh. 15 - Prob. 15.32PCh. 15 - Prob. 15.33PCh. 15 - Prob. 15.34PCh. 15 - 15-35 Following are structural formulas for three...Ch. 15 - Prob. 15.36PCh. 15 - 15-37 Consider a cyclohexane ring substituted with...Ch. 15 - Prob. 15.38PCh. 15 - Prob. 15.39PCh. 15 - Prob. 15.40PCh. 15 - 15-41 Compound A(C5Hh, is not optically active and...Ch. 15 - Prob. 15.42PCh. 15 - 15-43 Triamcinolone acetonide, the active...Ch. 15 - 15-44 Consider the structure of the...Ch. 15 - Prob. 15.45PCh. 15 - 15-46 Consider Lunesta, a nonbenzodiazepine...Ch. 15 - Prob. 15.47P
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