Organic Chemistry (8th Edition)
Organic Chemistry (8th Edition)
8th Edition
ISBN: 9780134042282
Author: Paula Yurkanis Bruice
Publisher: PEARSON
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Chapter 20.6, Problem 12P

a)

Interpretation Introduction

Interpretation:

The product formed from the reduction of D-idose is to be represented.

Concept Introduction:

Sodium borohydride is a strong reducing agent.  The carbonyl group in aldehydes and ketones can be reduced to an alcohol group by the compound sodium borohydride.  The product formed by the reduction is a polyalcohol and also known as alditol.

b)

Interpretation Introduction

Interpretation:

The product formed from the reduction of D-sorbose is to be outlined.

Concept Introduction:

Sodium borohydride is a strong reducing agent.  The carbonyl group in aldoses and ketones can be reduced to an alcohol group by the compound sodium borohydride with hydrolysis.  The product formed by the reduction is a polyalcohol and also known as alditol.

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a. How many stereogenic centers are present in α-D-galactose? b. Label the hemiacetal carbon in α-D-galactose. c. Draw the structure of β-D-galactose. d. Draw the structure of the polyhydroxy aldehyde that cyclizes to α- and β-D-galactose.
Draw the products formed when β-D-galactose is treated with each reagent. a. Ag2O + CH3I b. NaH + C6H5CH2Cl c. The product in (b), then H3O+ d. Ac2O + pyridine e. C6H5COCl + pyridine f. The product in (c), then C6H5COCl + pyridine
Which sugar will yield a single alditol upon reduction? A. Rhamnose B. Sorbose C. Xylulose D. Erythrulose

Chapter 20 Solutions

Organic Chemistry (8th Edition)

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