Problem_Set_12_solution - Chem 3580- Spring 2009 1. (a) OH...

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Chem 3580- Spring 2009 Problem Set 12 - Solutions 1. (a) O OH HO HO OH OH O OH HO HO OH OH ! -D-Mannopyranose " -D-Mannopyranose (b) O CH 2 OH HO OCH 3 O HO HO HO OCH 3 OH OH HO Methyl ! -D-mannopyranose 2. Recall that ketoses and aldoses can epimerize between one another. The reaction is usually catalyzed by both acids ad bases but it can also be catalyzed by water, albeit slowly. R O H OH OH R O OH H—OH R OH O H OH R OH O H—OH R OH O ketose enediol aldose H H H H H H CH 2 OH R O R OH H O OH R H HO O OH + 2-ketose aldonic acids Br 2 , H 2 O Br 2 , H 2 O 3. CH 2 OH CH 2 OH OH HO OH OH CH 2 OH CH 2 OH OH HO OH OH COOH COOH OH HO OH OH + CH 2 OH OH HO OH OH NPh (a) (b) (c) (d) (e) D-Glucose From C1-C5 From C6 O H OH O H H 5
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CH 2 OH CH 2 OH NPh HO OH OH D-Fructose CH 2 OH CHOH CH 2 OH HO OH OH (a) C2 Epimers CH 2 OH CHOH CH 2 OH HO OH OH (b) C2 Epimers COOH COOH O HO OH OH + (d) (c) (e) + O H H From C1 and C6 CO 2 From C2 From C3-C5 O H OH 3 2 4. O
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Problem_Set_12_solution - Chem 3580- Spring 2009 1. (a) OH...

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