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Unformatted text preview: OH + O O O + H OH + O O OH HO H OH OH O O H O HO PROBLEM 8 Trichloroethanol my be prepared by the direct reduction of chloral hydrate in water with sodium borohydride. Suggest a mechanism for this reaction. Take note that sodium borohydride does not displace hydroxide from carbon atoms! HO OH H Cl3C × NaBH4 OH Cl3C H2O chloral hydrate trichloroethanol H HO OH H H Cl3C H B H this is not the mechanism Purpose of the problem To help you detect bad mechanisms and find concealed good ones. Suggested solution If sodium borohydride doesn’t displace hydroxide from carbon atoms, then what does it do? We know it attacks carbonyl groups to give alcohols and to get trichloroethanol we should have to reduce chloral. Hemiacetals are in equilibrium with their carbonyl equivalents, so….. Cl3C H H O HO OH Cl3C H H H B H O Cl3C H H2O H HO H Cl3C H 7 8 Solutions Manual to accompany Organic Chemistry 2e PROBLEM...
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