When d-glucose is treated with aqueous sodium hydroxide, a complex mixture of
Chapter 24, Problem 24.85(choose chapter or problem)
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: C H OH HO H H OH H OH CH2OH OH C HO H H OH HO H HO H CH2OH OH D-Glucose L-Glucose NaOH H2O
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