Organic Chemistry (8th Edition)
Organic Chemistry (8th Edition)
8th Edition
ISBN: 9780134042282
Author: Paula Yurkanis Bruice
Publisher: PEARSON
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Chapter 25.3, Problem 4P

Draw the structure of an optically active fat that, when hydrolyzed under acidic conditions, gives the same products as the fat in problem 3.

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The tea leaves that contain the caffeine to be isolated are predominantly composed of cellulose, a natural and extremely abundant polymer of glucose. Look up the chair structure of B-D-glucose (B-D-glucopyranose, the monomer from which the cellulose polymer is composed). Draw this structure, draw the flipped chair, and indicate which conformer you think is more stable, if either. BRIEFLY explain your choice.
b) Compounds A and B have the following properties: Compound A (C5H1005) is an optically active D-pentose that exists exclusively as an acyclic molecule. (Hint: that sentence alone completely determines the structure of A! But we generously give you more information.) • Compound A does not react with Br₂/H₂O. • Reduction of A with NaBH4 gives only one product, B (C5H12O5), which is optically active. Write acyclic Fischer projection structures of A and B.
1. A carbohydrate has the molecular formula C6H12O6 and has three chiral carbons. Is this a ketohexose, an aldohexose, or an aldopentose? Explain2. Show the Fischer projection formula for the organic product of the reaction between D-ribose and warm, dilute nitric acid. Circle the carbons that are oxidized in this reaction.

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Organic Chemistry (8th Edition)

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