Organic Chemistry Plus Masteringchemistry With Pearson Etext, Global Edition
Organic Chemistry Plus Masteringchemistry With Pearson Etext, Global Edition
9th Edition
ISBN: 9781292151229
Author: Wade, LeRoy G.
Publisher: PEARSON
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Chapter 5, Problem 5.40SP
Interpretation Introduction

Interpretation: The absolute configuration of D-()-erythrose is to be identified with the knowledge of absolute configuration of D-(+)-erythrose.

Concept introduction: (R) or (S) configuration is assigned in fisher projections with the help of Cahn-Ingold-Prelog convention. Priorities are assigned to groups that are attached to chiral carbon atom. The direction of arrow from group 1 to group 2 to group 3 is analysed and then configuration is assigned according it.

To determine: The absolute configuration of D-()-erythrose on the basis of the knowledge of absolute configuration of D-(+)-erythrose.

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d-(-)-Erythrose has the formula HOCH2¬CH(OH)¬CH(OH)¬CHO, and the d in its name implies that it can be degraded to d-(+)-glyceraldehyde. The (-) in its name implies that d-(-)-erythrose is optically active (levorotatory). When d-(-)-erythrose is reduced (using H2 and a nickel catalyst), it gives an optically inactive product of formula HOCH2¬CH(OH)¬CH(OH)¬CH2OH. Knowing the absolute configuration of d-(+)-glyceraldehyde (Section 5-14), determine the absolute configuration of d-(-)-erythrose.
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