Organic Chemistry, Loose-leaf Version
Organic Chemistry, Loose-leaf Version
8th Edition
ISBN: 9781305865549
Author: William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher: Cengage Learning
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Chapter 25, Problem 25.17P

(a)

Interpretation Introduction

Interpretation:

The term pyranose has to be defined.

(b)

Interpretation Introduction

Interpretation:

The term furanose has to be defined.

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Identify the missing starting materials/ reagents/ products in the following reactions. Show the stereochemistry clearly in the structures, if any. If there is a major product, draw the structures of the major product with stereochemistry clearly indicated where applicable. Show only the diastereomers (you do not have to draw the pairs of enantiomers). If you believe that multiple products are formed in approximately equal amounts (hence neither is the major product), draw the structures of the products, and show the detailed mechanism of these reactions to justify the formation of the multiple products. If you believe no product is formed, explain why briefly. (6 mark for each, except f and g, which are 10 mark each)
3. What starting material would you use to synthesize 3-hydroxypentanoic acid using a NaBH4 reduction?
1. Give stereochemical (Fischer projection) formulas for all (but no extras) the stereoisomers that could theoretically form during the reduction of a. the carbonyl group of 2-methyl-3--pentanone b. both carbonyl groups of 2,4-pentanedione (careful!) 2. Predict the products of the reduction of O=CCH2CH2CH2C=O with a. LiAlH4 b. NaBH4 CH3 OH
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