Organic Chemistry&mod Mstg Etx Vp Ac Pkg
Organic Chemistry&mod Mstg Etx Vp Ac Pkg
1st Edition
ISBN: 9780134466729
Author: Bruice
Publisher: Pearson Education
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Chapter 20, Problem 44P
Interpretation Introduction

Interpretation:

The identification of compound A and B is to be stated.

Concept Introduction:

Sodium borohydride is a strong reducing agent. It reduces an aldehyde group into an alcohol.  The Wohl degradation is used in order to reduce the chain of an aldose by one carbon.  Thus, hexoses are reduces to pentoses, and pentoses are reduces to tetroses.

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Which D-aldopentose is oxidized to an optically active aldaric acid and undergoes the Wohl degradation to yield a D-aldotetrose that is oxidized to an optically active aldaric acid?
Treatment with NaBH 4 converts aldose U into an optically inactive (meso) alditol V. Ruff degradation ofU gives W, whose alditol is optically inactive. Ruff degradation of W forms D-glyceraldehyde, thesimplest aldose. Upon Kiliani-Fischer synthesis, U is converted to two aldoses, X and Y. X is oxidized toan optically active aldaric acid Z. Y is oxidized to an optically inactive aldaric acid. Draw the structuresof D-glyceraldehyde, V, W, X, Y, and Z. Structure of compound U is shown below.
The following isomerization reaction, drawn using D-glucose as starting material, occurs with all aldohexoses in the presence of base. Draw a stepwise mechanism that illustrates how each compound is formed.

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Organic Chemistry&mod Mstg Etx Vp Ac Pkg

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