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Problem_Set_12 - Chem 3580 Spring 2009 Problem Set 12 1(a...

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Chem 3580- Spring 2009 Problem Set 12 1. (a) Draw the chair form of α -D-mannopyranose and β -D-mannopyranose. (b) Draw the Haworth projection and chair conformation of methyl α -D-mannopyranose. 2. 2-Ketoses are reducing sugars because they can be oxidized to aldonic acids under mild oxidizing conditions similar to oxidation of aldoses. Provide the sequence of reactions that will lead to the oxidation. CH 2 OH R O R OH H O OH R H HO O OH + 2-ketose aldonic acids Br 2 , H 2 O 3. Draw the Fischer projections for the products formed by reaction of D-glucose and D-fructose with the following reagents: (a) 1. NaBH 4 2. H 3 O + (b) H 2 , Pt (c) HNO 3 , warm (d) one mol of H 5 IO 6 or HIO 4 (e) PhNH 2 4. Treat of β -D-glucopyranoside with benzaldehyde forms a stable cyclic acetal. Draw the most stable conformation of this acetal. Identify each new chiral center in the acetal. 5. Draw each of the following in the open-chain form as a Fischer projection. Name each sugar.
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