CHO CHO CHO CH,OH C=0 H HO H- OH но Но- H,0 Но HO- -H но -H но OH H- H- -O- H- HO- OH OH но- CH,OH ČH,OH CH,OH CH,OH D-glucose (recovered starting material)

Chemistry for Today: General, Organic, and Biochemistry
9th Edition
ISBN:9781305960060
Author:Spencer L. Seager, Michael R. Slabaugh, Maren S. Hansen
Publisher:Spencer L. Seager, Michael R. Slabaugh, Maren S. Hansen
Chapter14: Aldehydes And Ketones
Section: Chapter Questions
Problem 14.41E
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Question

The attached 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.

CHO
CHO
CHO
CH,OH
C=0
H
HO
H-
OH
но
Но-
H,0
Но
HO-
-H
но
-H
но
OH
H-
H-
-O-
H-
HO-
OH
OH
но-
CH,OH
ČH,OH
CH,OH
CH,OH
D-glucose
(recovered
starting material)
Transcribed Image Text:CHO CHO CHO CH,OH C=0 H HO H- OH но Но- H,0 Но HO- -H но -H но OH H- H- -O- H- HO- OH OH но- CH,OH ČH,OH CH,OH CH,OH D-glucose (recovered starting material)
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