Question: 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

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:

н. Н. Н- -ОН Но -н Но -н Н- ОН NaOH Н.о Н- -ОН Но- -Н Н. -ОН Но- -H- CH-он ČH,OH D-Glucose

. . - - - - - NaOH . - - - - . - - -H- CH- H,OH D-Glucose L-Glucose

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