Introduction to General, Organic and Biochemistry
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
Question
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Chapter 17, Problem 17.71P
Interpretation Introduction

(a)

Interpretation:

The structure of six-membered cyclic hemiacetal formed by 5-hydroxyhexanal should be drawn.

Concept Introduction:

Hemiacetal is a molecule formed by the addition of an alcohol to an aldehyde or ketone,containing a carbon bonded to one −OH group and one −OR group. For example-

Introduction to General, Organic and Biochemistry, Chapter 17, Problem 17.71P , additional homework tip  1

Expert Solution
Check Mark

Answer to Problem 17.71P

Introduction to General, Organic and Biochemistry, Chapter 17, Problem 17.71P , additional homework tip  2

Explanation of Solution

Reaction of the aldehyde group and the hydroxyl group forms a six-membered cyclic hemiacetal.

Introduction to General, Organic and Biochemistry, Chapter 17, Problem 17.71P , additional homework tip  3

Therefore, the structure hemiacetal formed from 5-hydroxyhexanalis as follows:

Introduction to General, Organic and Biochemistry, Chapter 17, Problem 17.71P , additional homework tip  4

Interpretation Introduction

(b)

Interpretation:

The number of possible stereoisomers of 5-hydroxyhexanal should be determined.

Concept Introduction:

Stereoisomers are the compounds that are differ only in the spatial arrangements of their atoms. For a molecule with n stereoisomers, a maximum of 2n stereoisomers are possible.

Expert Solution
Check Mark

Answer to Problem 17.71P

5-hydroxyhexanal has 2 stereoisomers.

Explanation of Solution

For a molecule with n stereoisomers, a maximum of 2n stereoisomers are possible.

Introduction to General, Organic and Biochemistry, Chapter 17, Problem 17.71P , additional homework tip  5

In 5-hydroxyhexanal, there is one stereocenter.

Therefore, number of stereoisomers can be calculated as follows:

Number of stereOisOmers = 2n= 21= 2

Thus, number of stereoisomers will be 2.

Interpretation Introduction

(c)

Interpretation:

The number of possible stereoisomers of hemiacetal of 5-hydroxyhexanal should be calculated.

Concept Introduction:

Stereoisomers are the compounds that are differ only in the spatial arrangements of their atoms. For a molecule with n stereoisomers, a maximum of 2n stereoisomers are possible.

Expert Solution
Check Mark

Answer to Problem 17.71P

Hemiacetal of 5-hydroxyhexanal has 4 stereoisomers.

Explanation of Solution

For a molecule with n stereoisomers, a maximum of 2n stereoisomers are possible.

Introduction to General, Organic and Biochemistry, Chapter 17, Problem 17.71P , additional homework tip  6

In hemiacetal of 5-hydroxyhexanal, there are two stereo centres.

Therefore, number of stereoisomers can be calculated as follows:

Number of stereOisOmers = 2n= 22= 4

Thus, number of stereoisomers are 4.

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Chapter 17 Solutions

Introduction to General, Organic and Biochemistry

Ch. 17 - 17-11 What is the difference in structure between...Ch. 17 - 17-12 Is it possible for the carbon atom of a...Ch. 17 - 17-13 Which compounds contain carbonyl groups?Ch. 17 - 17-14 Following are structural formulas for two...Ch. 17 - 17-15 Draw structural formulas for the four...Ch. 17 - Prob. 17.16PCh. 17 - Prob. 17.17PCh. 17 - 17-18 Draw structural formulas for these ketones....Ch. 17 - 17-19 Write the JUPAC names for these compounds.Ch. 17 - Prob. 17.20PCh. 17 - 17-2 1 Explain why each name is incorrect. Write...Ch. 17 - Prob. 17.22PCh. 17 - Prob. 17.23PCh. 17 - 17-24 In each pair of compounds, select the one...Ch. 17 - Prob. 17.25PCh. 17 - 17-26 Account for the fact that acetone has a...Ch. 17 - 17-27 Pentane, 1-butanol, and butanal all have...Ch. 17 - 17-28 Show how acetaldehyde can form hydrogen...Ch. 17 - 17-29 Why can’t two molecules of acetone form a...Ch. 17 - 17-30 Answer true or false. (a) The reduction of...Ch. 17 - 17-3 1 Draw a structural formula for the principal...Ch. 17 - Prob. 17.32PCh. 17 - 17-33 What simple chemical test could you use to...Ch. 17 - 17-34 Explain why liquid aldehydes are often...Ch. 17 - 17-35 Suppose that you take a bottle of...Ch. 17 - 17-36 Explain why the reduction of an aldehyde...Ch. 17 - Prob. 17.37PCh. 17 - Prob. 17.38PCh. 17 - Prob. 17.39PCh. 17 - Prob. 17.40PCh. 17 - Prob. 17.41PCh. 17 - Prob. 17.42PCh. 17 - Prob. 17.43PCh. 17 - Prob. 17.44PCh. 17 - Prob. 17.45PCh. 17 - Prob. 17.46PCh. 17 - 17-47 What is the characteristic structural...Ch. 17 - Prob. 17.48PCh. 17 - Prob. 17.49PCh. 17 - Prob. 17.50PCh. 17 - Prob. 17.51PCh. 17 - Prob. 17.52PCh. 17 - Prob. 17.53PCh. 17 - 17-54 Following is the structure of...Ch. 17 - Prob. 17.55PCh. 17 - Prob. 17.56PCh. 17 - Prob. 17.57PCh. 17 - Prob. 17.58PCh. 17 - Prob. 17.59PCh. 17 - 17-60 1-Propanol can be prepared by the reduction...Ch. 17 - Prob. 17.61PCh. 17 - 17-62 Show how to bring about these conversions....Ch. 17 - Prob. 17.63PCh. 17 - Prob. 17.64PCh. 17 - Prob. 17.65PCh. 17 - Prob. 17.66PCh. 17 - 17-67 Draw structural formulas for these...Ch. 17 - Prob. 17.68PCh. 17 - 17-69 Propanal (bp 49°C) and 1-propanol (bp 97°C)...Ch. 17 - 17-70 What simple chemical test could you use to...Ch. 17 - Prob. 17.71PCh. 17 - 17-72 The following molecule is an enediol; each...Ch. 17 - 17-73 Alcohols can be prepared by the...Ch. 17 - 17-74 Glucose, C6H12O6, contains an aldehyde group...Ch. 17 - Prob. 17.75PCh. 17 - Prob. 17.76PCh. 17 - Prob. 17.77PCh. 17 - 17-78 Complete the following equation for these...Ch. 17 - 17-79 Write an equation for each conversion. (a)...
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