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Solutions_Manual_for_Organic_Chemistry_6th_Ed 437

Solutions_Manual_for_Organic_Chemistry_6th_Ed 437 - (a...

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18-68 Building a model will help visualize this problem. ( a ) H I :O y O CH20H -" ": CH HO OH HO OH open-chain fonn OH OH w -- same as H H I I - :O y O CH20H + -"": CH HO y . y CH20H HO OH OH cyclic fonn-hemiacetal - H H I I :O y C :O CH20H " C H ·· + ( b ) Yes, the cyclic fonn of glucose will give a positive Tollens test. In the basic solution of the Tollens test, the hemiacetal is in equilibrium with the open-chain aldehyde with the cyclic fonn in much larger concentration. However, it is the open-chain aldehyde that reacts with silver ion, so even though there
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