Organic Chemistry (9th Edition)
Organic Chemistry (9th Edition)
9th Edition
ISBN: 9780321971371
Author: Leroy G. Wade, Jan W. Simek
Publisher: PEARSON
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Chapter 23, Problem 23.47SP

(a)

Interpretation Introduction

To draw: The chair conformation of β-D-mannopyranose.

Interpretation: The chair conformation of β-D-mannopyranose is to be drawn.

Concept introduction: Cyclic monosaccharides are drawn with the help of Fisher projection. The groups on the right side of fisher projection are projected downwards in the cyclic structure while groups on the left side are projected upwards. In Haworth projection or chair conformation, oxygen is present at the back, right-hand corner with C1 at the far right.

(b)

Interpretation Introduction

To draw: The chair conformation of α-D-allopyranose.

Interpretation: The chair conformation of α-D-allopyranose is to be drawn.

Concept introduction: Cyclic monosaccharides are drawn with the help of Fisher projection. The groups on the right side of fisher projection are projected downwards in the cyclic structure while groups on the left side are projected upwards. In Haworth projection or chair conformation, oxygen is present at the back, right-hand corner with C1 at the far right.

(c)

Interpretation Introduction

To draw: The chair conformation of β-D-galactopyranose.

Interpretation: The chair conformation of β-D-galactopyranose is to be drawn.

Concept introduction: Cyclic monosaccharides are drawn with the help of Fisher projection. The groups on the right side of fisher projection are projected downwards in the cyclic structure while groups on the left side are projected upwards. In Haworth projection or chair conformation, oxygen is present at the back, right-hand corner with C1 at the far right.

(d)

Interpretation Introduction

To draw: The chair conformation of N-acetylglucosamine.

Interpretation: The chair conformation of N-acetylglucosamine is to be drawn.

Concept introduction: Cyclic monosaccharides are drawn with the help of Fisher projection. The groups on the right side of fisher projection are projected downwards in the cyclic structure while groups on the left side are projected upwards. In Haworth projection or chair conformation, oxygen is present at the back, right-hand corner with C1 at the far right.

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Part D. Do the two structures A and B of each pair drawn below represent the same molecule, constitutional isomers, or stereoisomers? If A and B are stereoisomers, further classify them as enantiomers or diastereomers.
The following statements about the chair conformation of D glucopyranose are true EXCEPT * a. The axial positions are occupied by hydroxyl groups b. It is the more stable configuration of D-glucopyranose c. The Equatorial substituents about the ring are staggered so that they alternately extend above and below the mean plane of the ring d. The equatorial positions are occupied by hydroxyl groups
Part F. Draw the most stable sawhorse conformation of cis-1,3- diphenylcyclohexane. Part G. Draw the structure of meso-1,2-dimethylcyclopentane.

Chapter 23 Solutions

Organic Chemistry (9th Edition)

Ch. 23.4 - Prob. 23.11PCh. 23.5 - Prob. 23.12PCh. 23.5 - Prob. 23.13PCh. 23.6 - Prob. 23.14PCh. 23.6 - Prob. 23.15PCh. 23.7 - Prob. 23.16PCh. 23.7 - Prob. 23.17PCh. 23.7 - Two sugars, A and B, are known to be glucose and...Ch. 23.7 - Prob. 23.19PCh. 23.8 - Prob. 23.20PCh. 23.8 - Prob. 23.21PCh. 23.8 - Prob. 23.22PCh. 23.8 - Prob. 23.23PCh. 23.8 - Prob. 23.24PCh. 23.9 - a. Show the product that results when fructose is...Ch. 23.9 - Prob. 23.26PCh. 23.9 - Prob. 23.27PCh. 23.9 - Prob. 23.28PCh. 23.10 - Prob. 23.29PCh. 23.10 - Prob. 23.30PCh. 23.10 - Prob. 23.31PCh. 23.11 - Prob. 23.32PCh. 23.11 - The Wohl degradation, an alternative to the Ruff...Ch. 23.11 - Prob. 23.34PCh. 23.11 - Prob. 23.35PCh. 23.12A - Prob. 23.36PCh. 23.12A - Give an equation to show the reduction of Tollens...Ch. 23.12A - Prob. 23.38PCh. 23.12B - Prob. 23.39PCh. 23.12C - Prob. 23.40PCh. 23.12C - Prob. 23.41PCh. 23.13A - Prob. 23.42PCh. 23.15 - Cytosine, uracil, and guanine have tautomeric...Ch. 23.15 - a. An aliphatic aminoglycoside is relatively...Ch. 23.16C - Prob. 23.45PCh. 23 - Prob. 23.46SPCh. 23 - Prob. 23.47SPCh. 23 - Prob. 23.48SPCh. 23 - Prob. 23.49SPCh. 23 - Prob. 23.50SPCh. 23 - Prob. 23.51SPCh. 23 - Prob. 23.52SPCh. 23 - Prob. 23.53SPCh. 23 - Prob. 23.54SPCh. 23 - Prob. 23.55SPCh. 23 - Prob. 23.56SPCh. 23 - Prob. 23.57SPCh. 23 - Prob. 23.58SPCh. 23 - Prob. 23.59SPCh. 23 - Prob. 23.60SPCh. 23 - Prob. 23.61SPCh. 23 - Prob. 23.62SPCh. 23 - Prob. 23.63SPCh. 23 - Draw the structure of a four-residue segment of...Ch. 23 - Retroviruses like HIV, the pathogen responsible...Ch. 23 - Prob. 23.66SPCh. 23 - Prob. 23.67SP
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