The enediol tautomerizes to a ketose sugar before the next mechanistic step. Draw all lone pairs and curved arrows that lead to that tautomer. OH H OH -OH -OH Yih H- H- -OH H- -OH HO HO H- H- OH HO Edit Drawing Draw curved arrows and lone pairs for step 5 of the mechanism. OH OH -OH OH H₂O -OH 4th -OH 1 -OH H- 44th HO

Organic Chemistry
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Chapter22: Carbonyl Alpha-substitution Reactions
Section22.SE: Something Extra
Problem 30MP: One of the later steps in glucose biosynthesis is the isomerization of fructose 6-phosphate to...
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When D-glucose is treated with aqueous sodium hydroxide, a complex mixture of carbohydrates is formed, including D-mannose and
D-fructose. Over time, almost all aldohexoses will be present in the mixture. Even L-glucose can be detected, albeit in very small
concentrations.
Using the fewest number of mechanistic steps possible, draw a reasonable mechanism showing the formation of: L-glucose from D-
glucose.
Transcribed Image Text:When D-glucose is treated with aqueous sodium hydroxide, a complex mixture of carbohydrates is formed, including D-mannose and D-fructose. Over time, almost all aldohexoses will be present in the mixture. Even L-glucose can be detected, albeit in very small concentrations. Using the fewest number of mechanistic steps possible, draw a reasonable mechanism showing the formation of: L-glucose from D- glucose.
The enediol tautomerizes to a ketose sugar before the next mechanistic step. Draw all lone pairs and curved arrows that lead to
that tautomer.
HO
OH
OH
-OH
Yih
H-
H-
-OH
-OH
HO
H-
OH
H-
H-
-OH
HO
Edit Drawing
Draw curved arrows and lone pairs for step 5 of the mechanism.
OH
+ H₂O
OH
-OH
4th
HO
-OH
1
-OH
-OH
49th
Transcribed Image Text:The enediol tautomerizes to a ketose sugar before the next mechanistic step. Draw all lone pairs and curved arrows that lead to that tautomer. HO OH OH -OH Yih H- H- -OH -OH HO H- OH H- H- -OH HO Edit Drawing Draw curved arrows and lone pairs for step 5 of the mechanism. OH + H₂O OH -OH 4th HO -OH 1 -OH -OH 49th
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