ORGANIC CHEMISTRY
ORGANIC CHEMISTRY
5th Edition
ISBN: 9781259977596
Author: SMITH
Publisher: MCG
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Chapter 28, Problem 28.42P
Interpretation Introduction

(a)

Interpretation: The relationship between ORGANIC CHEMISTRY, Chapter 28, Problem 28.42P , additional homework tip  1 and ORGANIC CHEMISTRY, Chapter 28, Problem 28.42P , additional homework tip  2 is to be stated.

Concept introduction: The anomers are cyclic monosaccharides, which differ in configuration at one stereogenic centre. These carbon atoms are called anomeric centre.

Expert Solution
Check Mark

Answer to Problem 28.42P

The compounds ORGANIC CHEMISTRY, Chapter 28, Problem 28.42P , additional homework tip  3 and ORGANIC CHEMISTRY, Chapter 28, Problem 28.42P , additional homework tip  4 are epimers.

Explanation of Solution

The structures of compounds ORGANIC CHEMISTRY, Chapter 28, Problem 28.42P , additional homework tip  5 and ORGANIC CHEMISTRY, Chapter 28, Problem 28.42P , additional homework tip  6 are,

ORGANIC CHEMISTRY, Chapter 28, Problem 28.42P , additional homework tip  7

Figure 1

In the given structures, the configuration at ORGANIC CHEMISTRY, Chapter 28, Problem 28.42P , additional homework tip  8 is different. Hence, the compounds ORGANIC CHEMISTRY, Chapter 28, Problem 28.42P , additional homework tip  9 and ORGANIC CHEMISTRY, Chapter 28, Problem 28.42P , additional homework tip  10 are epimers.

Conclusion

The compounds ORGANIC CHEMISTRY, Chapter 28, Problem 28.42P , additional homework tip  11 and ORGANIC CHEMISTRY, Chapter 28, Problem 28.42P , additional homework tip  12 are epimers.

Interpretation Introduction

(b)

Interpretation: The relationship between ORGANIC CHEMISTRY, Chapter 28, Problem 28.42P , additional homework tip  13 and ORGANIC CHEMISTRY, Chapter 28, Problem 28.42P , additional homework tip  14 is to be stated.

Concept introduction: The anomers are cyclic monosaccharides, which differ in configuration at one stereogenic centre. These carbon atoms are called anomeric centre. The compounds which are neither mirror images nor supperimposable on each other are known as diastereomer.

Expert Solution
Check Mark

Answer to Problem 28.42P

The compound ORGANIC CHEMISTRY, Chapter 28, Problem 28.42P , additional homework tip  15 and ORGANIC CHEMISTRY, Chapter 28, Problem 28.42P , additional homework tip  16 are diastreomers but not epimers.

Explanation of Solution

The structures of given compound ORGANIC CHEMISTRY, Chapter 28, Problem 28.42P , additional homework tip  17 and ORGANIC CHEMISTRY, Chapter 28, Problem 28.42P , additional homework tip  18 are,

ORGANIC CHEMISTRY, Chapter 28, Problem 28.42P , additional homework tip  19

Figure 2

In the given structures, the compound ORGANIC CHEMISTRY, Chapter 28, Problem 28.42P , additional homework tip  20 is not mirror image of compound ORGANIC CHEMISTRY, Chapter 28, Problem 28.42P , additional homework tip  21 and the configuration of more than is different. Hence, the compound ORGANIC CHEMISTRY, Chapter 28, Problem 28.42P , additional homework tip  22 and ORGANIC CHEMISTRY, Chapter 28, Problem 28.42P , additional homework tip  23 are diastreomers but not epimers.

Conclusion

The compound ORGANIC CHEMISTRY, Chapter 28, Problem 28.42P , additional homework tip  24 and ORGANIC CHEMISTRY, Chapter 28, Problem 28.42P , additional homework tip  25 are diastreomers but not epimers.

Interpretation Introduction

(c)

Interpretation: The relationship between ORGANIC CHEMISTRY, Chapter 28, Problem 28.42P , additional homework tip  26 and ORGANIC CHEMISTRY, Chapter 28, Problem 28.42P , additional homework tip  27 is to be stated.

Concept introduction: The compounds which are mirror images as well as non-supperimposable on each other. These compounds are known as enantiomers.

Expert Solution
Check Mark

Answer to Problem 28.42P

The compound ORGANIC CHEMISTRY, Chapter 28, Problem 28.42P , additional homework tip  28 and ORGANIC CHEMISTRY, Chapter 28, Problem 28.42P , additional homework tip  29are enantiomers.

Explanation of Solution

The structures of given compound ORGANIC CHEMISTRY, Chapter 28, Problem 28.42P , additional homework tip  30 and ORGANIC CHEMISTRY, Chapter 28, Problem 28.42P , additional homework tip  31 are,

ORGANIC CHEMISTRY, Chapter 28, Problem 28.42P , additional homework tip  32

Figure 3

In the given structures, the compound ORGANIC CHEMISTRY, Chapter 28, Problem 28.42P , additional homework tip  33 is mirror image of compound ORGANIC CHEMISTRY, Chapter 28, Problem 28.42P , additional homework tip  34. Hence, the compound ORGANIC CHEMISTRY, Chapter 28, Problem 28.42P , additional homework tip  35 and ORGANIC CHEMISTRY, Chapter 28, Problem 28.42P , additional homework tip  36 are enantiomers.

Conclusion

The compound ORGANIC CHEMISTRY, Chapter 28, Problem 28.42P , additional homework tip  37 and ORGANIC CHEMISTRY, Chapter 28, Problem 28.42P , additional homework tip  38are enantiomers.

Interpretation Introduction

(d)

Interpretation: The relationship between ORGANIC CHEMISTRY, Chapter 28, Problem 28.42P , additional homework tip  39 and ORGANIC CHEMISTRY, Chapter 28, Problem 28.42P , additional homework tip  40 is to be stated.

Concept introduction: The compounds which have same molecular formula but differ in connectivity of the substituents. These compounds are known as constitutional isomers.

Expert Solution
Check Mark

Answer to Problem 28.42P

The compound ORGANIC CHEMISTRY, Chapter 28, Problem 28.42P , additional homework tip  41 and ORGANIC CHEMISTRY, Chapter 28, Problem 28.42P , additional homework tip  42 are constitutional isomers.

Explanation of Solution

The structures of given compound ORGANIC CHEMISTRY, Chapter 28, Problem 28.42P , additional homework tip  43 and ORGANIC CHEMISTRY, Chapter 28, Problem 28.42P , additional homework tip  44 are,

ORGANIC CHEMISTRY, Chapter 28, Problem 28.42P , additional homework tip  45

Figure 4

In the given structures, the molecular formula of ORGANIC CHEMISTRY, Chapter 28, Problem 28.42P , additional homework tip  46 is same to the molecular formula of ORGANIC CHEMISTRY, Chapter 28, Problem 28.42P , additional homework tip  47 but the connectivity of substituents at ORGANIC CHEMISTRY, Chapter 28, Problem 28.42P , additional homework tip  48 is different. Hence, the compound ORGANIC CHEMISTRY, Chapter 28, Problem 28.42P , additional homework tip  49 and ORGANIC CHEMISTRY, Chapter 28, Problem 28.42P , additional homework tip  50 are constitutional isomers.

Conclusion

The compound ORGANIC CHEMISTRY, Chapter 28, Problem 28.42P , additional homework tip  51 and ORGANIC CHEMISTRY, Chapter 28, Problem 28.42P , additional homework tip  52 are constitutional isomers.

Interpretation Introduction

(e)

Interpretation: The relationship between ORGANIC CHEMISTRY, Chapter 28, Problem 28.42P , additional homework tip  53 and ORGANIC CHEMISTRY, Chapter 28, Problem 28.42P , additional homework tip  54 is to be stated.

Concept introduction: The anomers are cyclic monosaccharides, which differ in configuration at one stereogenic centre. These carbon atoms are called anomeric centre. The compounds which are neither mirror images nor supperimposable on each other are known as diastereomer.

Expert Solution
Check Mark

Answer to Problem 28.42P

The compounds ORGANIC CHEMISTRY, Chapter 28, Problem 28.42P , additional homework tip  55 and ORGANIC CHEMISTRY, Chapter 28, Problem 28.42P , additional homework tip  56 are diastreomers but not epimers.

Explanation of Solution

The substituents on a carbon are present above the ring in Haworth projection indicates that these bonds are above the plane (i.e. either equatorial or axial position) in chair form. The structures of given compound ORGANIC CHEMISTRY, Chapter 28, Problem 28.42P , additional homework tip  57 and ORGANIC CHEMISTRY, Chapter 28, Problem 28.42P , additional homework tip  58 are,

ORGANIC CHEMISTRY, Chapter 28, Problem 28.42P , additional homework tip  59

Figure 5

In the given structures, the configuration at ORGANIC CHEMISTRY, Chapter 28, Problem 28.42P , additional homework tip  60 is different which shows that the compound ORGANIC CHEMISTRY, Chapter 28, Problem 28.42P , additional homework tip  61 is not mirror image of compound ORGANIC CHEMISTRY, Chapter 28, Problem 28.42P , additional homework tip  62 and. Hence, the compound ORGANIC CHEMISTRY, Chapter 28, Problem 28.42P , additional homework tip  63 and ORGANIC CHEMISTRY, Chapter 28, Problem 28.42P , additional homework tip  64 are diastreomers but not epimers.

Conclusion

The compounds ORGANIC CHEMISTRY, Chapter 28, Problem 28.42P , additional homework tip  65 and ORGANIC CHEMISTRY, Chapter 28, Problem 28.42P , additional homework tip  66 are diastreomers but not epimers.

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Chapter 28 Solutions

ORGANIC CHEMISTRY

Ch. 28 - Prob. 28.11PCh. 28 - Prob. 28.12PCh. 28 - Prob. 28.13PCh. 28 - Prob. 28.14PCh. 28 - Prob. 28.15PCh. 28 - Prob. 28.16PCh. 28 - Prob. 28.17PCh. 28 - Draw a stepwise mechanism for the following...Ch. 28 - Prob. 28.19PCh. 28 - Prob. 28.20PCh. 28 - Prob. 28.21PCh. 28 - Prob. 28.22PCh. 28 - Draw the products formed when D-arabinose is...Ch. 28 - Prob. 28.24PCh. 28 - Prob. 28.25PCh. 28 - Prob. 28.26PCh. 28 - Prob. 28.27PCh. 28 - Prob. 28.28PCh. 28 - Prob. 28.29PCh. 28 - Prob. 28.30PCh. 28 - Prob. 28.31PCh. 28 - Prob. 28.32PCh. 28 - Prob. 28.33PCh. 28 - Prob. 28.34PCh. 28 - Problem-28.35 Draw the structures of the...Ch. 28 - Prob. 28.36PCh. 28 - 28.37 Convert each ball-and-stick model to a...Ch. 28 - Prob. 28.38PCh. 28 - Prob. 28.39PCh. 28 - 28.40 Convert each compound to a Fischer...Ch. 28 - Prob. 28.41PCh. 28 - Prob. 28.42PCh. 28 - 28.43 Draw a Haworth projection for each compound...Ch. 28 - Prob. 28.44PCh. 28 - 28.45 Draw both pyranose anomers of each...Ch. 28 - Prob. 28.46PCh. 28 - Prob. 28.47PCh. 28 - Prob. 28.48PCh. 28 - Prob. 28.49PCh. 28 - 28.50 Draw the products formed when D-altrose is...Ch. 28 - Prob. 28.51PCh. 28 - Prob. 28.52PCh. 28 - Prob. 28.53PCh. 28 - Prob. 28.54PCh. 28 - Prob. 28.55PCh. 28 - Prob. 28.56PCh. 28 - Prob. 28.57PCh. 28 - 28.58 Draw a stepwise mechanism for the following...Ch. 28 - Prob. 28.59PCh. 28 - Prob. 28.60PCh. 28 - Prob. 28.61PCh. 28 - Prob. 28.62PCh. 28 - Prob. 28.63PCh. 28 - Prob. 28.64PCh. 28 - Prob. 28.65PCh. 28 - Prob. 28.66PCh. 28 - Prob. 28.67PCh. 28 - Prob. 28.68PCh. 28 - Prob. 28.69PCh. 28 - Prob. 28.70PCh. 28 - 28.71 Draw a stepwise mechanism for the following...
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