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Introduction to General, Organic a...

11th Edition
Frederick A. Bettelheim + 4 others
Publisher: Cengage Learning
ISBN: 9781285869759

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Chapter
Section
BuyFindarrow_forward

Introduction to General, Organic a...

11th Edition
Frederick A. Bettelheim + 4 others
Publisher: Cengage Learning
ISBN: 9781285869759
Chapter 20, Problem 20.35P
Textbook Problem
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5 Reduction of D-glucose by NaBH4 gives D-sorbitol, a compound used in the manufacture of sugar-free gums and candies. Draw a structural formula for D-sorbitol.

Interpretation Introduction

Interpretation:

The structural formula for D-sorbitol should be drawn.

Concept Introduction:

The sodium borohydride is a reducing agent, so it reduces the functional group present in the carbohydrate and itself get oxidized.

The reduction of aldehyde results in the formation of alcohol because reduction can also be defined as addition of hydrogen atom thus, -CHO group becomes -CH2 OH after addition of two hydrogen atoms on carbonyl carbon of the aldehydic group.

Explanation of Solution

The reduction D-Glucose with NaBH4 can be explained as follows:

  • D-Glucose is aldohexoses which possess aldehydic carbonyl group at C-1.
  • This carbonyl group undergoes reduction with NaBH4 and gets converted to −CH2 OH which is known as D-Sorbitol...

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Chapter 20 Solutions

Introduction to General, Organic and Biochemistry
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Ch. 20 - 1 What does it mean to say that D- and...Ch. 20 - 2 Explain the meaning of the designations D and L...Ch. 20 - 3 Which carbon of an aldopentose determines...Ch. 20 - 4 How many stereocenters are present in D-glucose?...Ch. 20 - 5 Which of the following compounds are...Ch. 20 - 6 Draw Fischer projections for L-ribose and...Ch. 20 - 7 Draw a Fischer projection for a D-2-ketoheptose.Ch. 20 - 8 Explain why all mono- and disaccharides are...Ch. 20 - .19 What is an amino sugar? Name the three amino...Ch. 20 - 0 Define the term anomeric carbon. Which carbon is...Ch. 20 - 1 Define (a) pyranose and (b) furanose.Ch. 20 - 2 Explain the conventions for using ( and ( to...Ch. 20 - 3 Are (-D-glucose and (-D-glucose anomers?...Ch. 20 - 4 Are the hydroxyl groups on carbons 1,2,3, and 4...Ch. 20 - 5 In what way are chair conformations a more...Ch. 20 - 6 Convert each of the following Haworth...Ch. 20 - 7 Convert each of the following chair...Ch. 20 - 8 Explain the phenomenon of mutarotation. How is...Ch. 20 - 9 The specific rotation of (-D-glucose is +112.2°....Ch. 20 - 0 When (-D-glucose is dissolved in water, the...Ch. 20 - 1 Define the terms glycoside and glycosidic bond.Ch. 20 - 2 What is the difference in meaning between the...Ch. 20 - Do glycosides undergo mutarotation?Ch. 20 - 4 Draw Fischer projections for the product formed...Ch. 20 - 5 Reduction of D-glucose by NaBH4 gives...Ch. 20 - 6 Reduction of D-fructose by NaBH4 gives two...Ch. 20 - 7 Ribitol and (-D-rihose 1-phosphate are...Ch. 20 - 8 Name three important disaccharides. From which...Ch. 20 - 9 What does it mean to describe a glycosidic bond...Ch. 20 - 0 Both maltose and lactose are reducing sugars,...Ch. 20 - 1 Following is a structural formula for a...Ch. 20 - 2 The disaccharide trehalose is found in young...Ch. 20 - 3 What is the difference in structure between...Ch. 20 - 4 Name three polysaccharides that are composed of...Ch. 20 - 5 Starch can be separated into two principal...Ch. 20 - 6 Where is glycogen stored in the human body?Ch. 20 - 7 Why is cellulose insoluble in water?Ch. 20 - 8 How is it possible that cows can digest grass...Ch. 20 - 9 A Fischer projection of N-acetyl-D-glucosamine...Ch. 20 - 0 Propose structural formulas for the repeating...Ch. 20 - 1 Hyaluronic acid acts as a lubricant in the...Ch. 20 - 2 The anticlotting property of heparin is partly...Ch. 20 - 3 (Chemical Connections 20A) Why does congenital...Ch. 20 - 4 (Chemical Connections 20B) What is the...Ch. 20 - 5 (Chemical Connections 20B) When L-ascorbic acid...Ch. 20 - 6 (Chemical Connections 20C) Why is the glucose...Ch. 20 - 7 (Chemical Connections 20D) What monosaccharides...Ch. 20 - 8 (Chemical Connections 20D) L-Fucose is a...Ch. 20 - 9 (Chemical Connections 20D) Why can’t a person...Ch. 20 - 0 (Chemical Connections 20E) Low-fat and...Ch. 20 - 1 2,6-Dideoxy-D-altrose, also known as...Ch. 20 - 2 In making candy or sugar syrups, sucrose is...Ch. 20 - 3 Hot-water extracts of ground willow bark are an...Ch. 20 - 4 Show how D-sorbitol, used in “sugarless” chewing...Ch. 20 - 5 Carbohydrates in most foods have roughly the...Ch. 20 - 6 Ribose and fructose have an important similarity...Ch. 20 - 7 In Section 20-4A, two structures are shown for...Ch. 20 - 8 Blood samples for research or medical tests...Ch. 20 - 9 What is the difference in the glycosidic bonds...Ch. 20 - 0 What are the structural differences between...Ch. 20 - 1 A substance called laetrile is structurally...Ch. 20 - 2 Why are five- and six-membered rings encountered...Ch. 20 - 3 What is the structural difference between...Ch. 20 - 4 Concentrated sulfuric acid can be used as a...Ch. 20 - 5 Chitin is a polysaccharide found in shrimp and...Ch. 20 - 6 In Section 20-2, we saw that in glucose, all...Ch. 20 - 7 An important part of the concern about the link...Ch. 20 - 8 Why would diabetics pay attention to the...Ch. 20 - 9 Supplements containing chondroitin sulfate are...Ch. 20 - 0 Would you expect a conformation of (-D-glucose...Ch. 20 - 1 One pathway for the metabolism of D-glucose-...Ch. 20 - 2 One step in glycolysis, the pathway that...Ch. 20 - 3 Following is a Haworth projection and a chair...Ch. 20 - 4 Below is the structural formula of coenzyme A,...Ch. 20 - 5 Vanillin (4-hydroxy-3-methoxybenzaldehyde), the...Ch. 20 - 6 The structure of the repeating disaccharide of...Ch. 20 - .87 The structure of lignin is shown below. This...Ch. 20 - 8 Most animals, including insects, cannot...Ch. 20 - 9 Paper consists primarily of cellulose fibers...

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