EBK GENERAL, ORGANIC, & BIOLOGICAL CHEM
EBK GENERAL, ORGANIC, & BIOLOGICAL CHEM
3rd Edition
ISBN: 9781259298424
Author: SMITH
Publisher: VST
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Chapter 15.7, Problem 15.20P
Interpretation Introduction

(a)

Interpretation:

Whether cholesterol is dextrorotatory or levorotatory needs to be identified.

Concept introduction:

A compound is dextrorotatory if it rotates the plane polarize light to the right or clockwise direction and it is levorotatory if the plane of polarize light rotates to left or anticlockwise.

Interpretation Introduction

(b)

Interpretation:

The specific rotation of the enantiomer of cholesterol needs to be determined.

Concept introduction:

Enantiomers are a part of stereoisomers. In chemistry, enantiomers are two stereoisomers that are mirror images of each other. Usually in a pair of enantiomers of a same compound one is dextrorotatory, while the other is levorotatory. As enantiomers have chiral centers, they are optical isomers.

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(a) assign R or S configuration to each chiral center, (b) Which compound are enantiomers? (c) Which compounds are diastereomers?
(a) Locate the stereogenic centers in the ball-and-stick model of lisinopril, a drug used to treat high blood pressure. (b) Label each stereogenic center as R or S.
Coibacin B (shown below) is a natural product that exhibits potent anti-inflammatory activity and potential activity in the treatment of leishmaniasis, a disease caused by certain parasites (Org. Lett. 2012, 14, 3878-3881): (a) Assign the configuration (R or S) of each chirality center (labeled A to C) in coibacin B. (b) Identify the number of possible stereoisomers for this compound, assuming that the geometry of the alkenes are fixed. Choices are given below and write the CAPITAL LETTER of your choice. A. 2 В. 4 С. 8 D. 16 ANSWERS: (a) A. В. C. (b)

Chapter 15 Solutions

EBK GENERAL, ORGANIC, & BIOLOGICAL CHEM

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