When an optically active D-aldopentose was subjected to Kiliani-Fischer synthesis, followed by NaBH4/H20, it produced a mixture of an optically active and an optically inactive alditol. When the same D-aldopentose was subjected to Wohl degradation followed by HNO3 it produced an optically inactive aldaric acid. Provide the structure of this D-aldopentose.

Organic Chemistry
8th Edition
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Chapter16: Aldehydes And Ketones
Section: Chapter Questions
Problem 16.70P
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When an optically active D-aldopentose was subjected to Kiliani-Fischer synthesis,
followed by NaBH4/H2O, it produced a mixture of an optically active and an
optically inactive alditol. When the same D-aldopentose was subjected to Wohl
degradation followed by HNO3 it produced an optically inactive aldaric acid. Provide
the structure of this D-aldopentose.
Н-
НО-
н-
H
-ОН НО
-H
Н-
-Н
CH₂OH
1
A) 1
B) II
C) III
осн
H
D) IV
НО
осн
-H Н-
-OH H-
H HỌ
CH₂OH
П
-OH H
-OH H
Н
-H
CH₂OH
Ш
_H
-OH HO
-OH H-
-OH H-
осн
-H
-OH
CH₂OH
IV
-OH
CH₂OH
V
Transcribed Image Text:When an optically active D-aldopentose was subjected to Kiliani-Fischer synthesis, followed by NaBH4/H2O, it produced a mixture of an optically active and an optically inactive alditol. When the same D-aldopentose was subjected to Wohl degradation followed by HNO3 it produced an optically inactive aldaric acid. Provide the structure of this D-aldopentose. Н- НО- н- H -ОН НО -H Н- -Н CH₂OH 1 A) 1 B) II C) III осн H D) IV НО осн -H Н- -OH H- H HỌ CH₂OH П -OH H -OH H Н -H CH₂OH Ш _H -OH HO -OH H- -OH H- осн -H -OH CH₂OH IV -OH CH₂OH V
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