GENERAL,ORGANIC, & BIOLOGICAL CHEM-ACCES
GENERAL,ORGANIC, & BIOLOGICAL CHEM-ACCES
4th Edition
ISBN: 9781265982959
Author: SMITH
Publisher: MCG
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Chapter 15.7, Problem 15.6PP
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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31. Which of the following statements about cholesterol is not correct? CH. HO Cholesterol 16 (a) Cholesterol is a steroid that contains a tetracyclic ring system. (b) Cholesterol is a steroid that contains 8 chiral carbons and can form 28 or 256 stereoisomers. (c) Each atom or group attached to a ring-junction carbon (i.e., carbons a-e) is in a trans or axial position. Because of this the tetracyclic ring system is mostly flat. (d) Cholesterol is used to synthesized vitamin D, bile acids, sex hormones, and adrenocorticoid hormones. (e) Cholesterol is not found in the cell membranes of animals.
Draw a chair conformation for the b-anomer of a disaccharide in which two units of d-glucopyranose are joined by an a-1,6-glycosidic bond.
Lactose is a disaccharide in which a glycosidic linkage connects the monosaccharides galactose and glucose. OH НО OH (a) Identify the glycosidic linkage and the acetal carbon in lactose. (b) What type of glycosidic linkage does lactose have (i.e., is it 1,1'-, 1,2'-, etc., and is it a or B)? (c) People who are lactose intolerant are deficient in the enzyme lactase, and therefore cannot efficiently break down the disaccharide into its monosaccharides. When lactose is treated with aqueous acid, however, this hydrolysis can take place, though relatively slowly. Draw the complete, detailed mechanism and the products of the acid-catalyzed hydrolysis of lactose. Но ОН НО ОН ОН Lactose

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GENERAL,ORGANIC, & BIOLOGICAL CHEM-ACCES

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