Essential Organic Chemistry, Global Edition
Essential Organic Chemistry, Global Edition
3rd Edition
ISBN: 9781292089034
Author: Paula Yurkanis Bruice
Publisher: PEARSON
Question
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Chapter 4.10, Problem 32P

(a)

Interpretation Introduction

Interpretation:

The number of asymmetric centers present in the given structure of cholesterol has to be determined.

Concept introduction:

Stereoisomers are isomers which have different spatial arrangement in spite of same bond connectivity.  Stereoisomers are due to the presence of stereocenter.  Stereocenter may be an atom axis (bond) or plane from which interchanging of two groups leads to stereoisomers.

Asymmetric center is a stereocenter which arises in hydrocarbons if the carbon is bonded to four different groups. 

(b)

Interpretation Introduction

Interpretation:

The number of possible stereoisomers of cholesterol present in nature has to be determined.

Concept introduction:

Stereoisomers are isomers which have different spatial arrangement in spite of same bond connectivity.  Stereoisomers are due to the presence of stereocenter.  Asymmetric centers are Stereocenter.

The equation for finding Stereoisomers from number of asymmetric centers in compounds is 2n, in which ‘n’ is the number of asymmetric centers.

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3) Give an example of: a. A compound with 2 or more stereocenters that is superimposable on its mirror image. b. A pair of compounds that are chiral but are non-superimposable and non-mirror images. c. A pair of compounds with 2 or more stereocenters that are non-superimposable and mirror images.
Identify the configuration for the indicated chiral centers.,To preview image click here A. B. C. HO CI CI a. a. OH Br S HIN b. יוו Br - b. CI b. H Bronchodilator and decongestant Hc. H N Antitumor agent H Vitamin B7
Considerthe image below. a. Draw the mirror image of structure I and label it as structure II.b. Are I and II chiral?c. What kind of stereocenters do they represent?

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