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Dehydration mechanism C C C C C C HO OH H 2OH OH OH H H H H - OH C C C C C C H 2O - OH H 2OH OH OH H H H H - O H H + + C C C C C C OH H 2OH - OH OH H H H H = O H 2O, H + 1. dehydration (elimination) 2. isomerization enediol C C C C C C - OH H 2OH H - H - - H H = O = O H - - OH dicarbonyl H new resonance, isomerizationDehydration mechanism C C C C C C HO OH H 2OH OH OH H H H H - OH C C C C C C H 2O - OH H 2OH OH OH H H H H - O H H + + C C C C C C OH H 2OH - OH OH H H H H = O H 2O, H + 1. dehydration (elimination) 2. isomerization enediol C C C C C C - OH H 2OH H - H - - H H = O = O H - - OH dicarbonyl H new resonance, isomerization