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 17.76P
Interpretation Introduction

(a)

Interpretation:

The differences in the structural formula of testosterone and methandrostenolone should be determined along with functional groups present in the structure.

Introduction to General, Organic and Biochemistry, Chapter 17, Problem 17.76P , additional homework tip  1

Introduction to General, Organic and Biochemistry, Chapter 17, Problem 17.76P , additional homework tip  2

Concept Introduction:

Steroids are the third major class of lipids. These are the compounds containing the following ring system:

Introduction to General, Organic and Biochemistry, Chapter 17, Problem 17.76P , additional homework tip  3

Expert Solution
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Answer to Problem 17.76P

Both methandrostenolone and testosterone hormone contains hydroxyl functional group (alcohol) and carbonyl functional group (kentone).

In the structural formula of testosterone hormone, there is only one double bond and it has only one methyl group attached to cyclopentane ring whereas in methandrostenolone there are two double bonds and two methyl groups are attached to the cyclopentane ring.

Explanation of Solution

Testosterone and methandrostenolone both the hormones contain one −OH group attached to cyclopentane ring and one >C=O group in cyclohexene ring. Therefore both alcoholic and ketone functional groups present in both hormones.

In the structure of testosterone there is only a double bond in cyclohexene ring having ketonic group and no methyl group is present on the carbon of cyclopentane ring having alcoholic group as shown:

Introduction to General, Organic and Biochemistry, Chapter 17, Problem 17.76P , additional homework tip  4

In the structure of methandrostenolone, there are two double bonds in cyclohexene ring having ketonic group and one methyl group attached on the carbon of cyclopentane ring having alcoholic group as shown:

Introduction to General, Organic and Biochemistry, Chapter 17, Problem 17.76P , additional homework tip  5

Interpretation Introduction

(b)

Interpretation:

In both the given hormones mark all the stereocenters and state the number of stereoisomer possible for each.

Introduction to General, Organic and Biochemistry, Chapter 17, Problem 17.76P , additional homework tip  6

Introduction to General, Organic and Biochemistry, Chapter 17, Problem 17.76P , additional homework tip  7

Concept Introduction:

Stereoisomers are the compounds that are differ only in the spatial arrangement of their atoms. Each stereoisomer has at least one stereocenter. A stereocenter is a tetrahedral carbon atom that has four different groups bonded to it. For a molecule with n sterocenters, a maximum of 2n stereoisomers are possible.

Expert Solution
Check Mark

Answer to Problem 17.76P

Stereocenters in testosterone:

Since testosterone has six stereocenters therefore it has 64 possible stereoisomers.

Stereocenters in methandrostenolone:

Since methandrostenolone has six stereocenters therefore it has 64 possible stereoisomers.

Explanation of Solution

A stereocenter is a tetrahedral carbon atom that has four different groups bonded to it.

Stereocenters in testosterone:

In testosterone there are six stereocenters.

Introduction to General, Organic and Biochemistry, Chapter 17, Problem 17.76P , additional homework tip  8

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

Number of stereOisOmers of testOsterOne= 2nHere,n=6numberofstereOisOmersoftestOsterOne=26 =64

Stereocenters in methandrostenolone:

In methandrostenolone there are six stereocenters.

Introduction to General, Organic and Biochemistry, Chapter 17, Problem 17.76P , additional homework tip  9

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

Number of stereOisOmers of metHandrOstenOlOne= 2nHere,n=6numberofstereOisOmersofmetHandrOstenOlOne=26 =64.

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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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