L34 - Predict Predict the initial product of the following reaction sequence H OH H O HO HO H H HO H OH NEt3 CH3 I H 3O H2O Predict the product of

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Unformatted text preview: Predict Predict the initial product of the following reaction sequence. H OH H O HO HO H H HO H OH NEt3 CH3 I H 3O H2O Predict the product of the following reaction. H OH a mono methyl ether OH OH H HO H CH3OH H HO H HO HO H O H OH H H OH OH O OH O H O H3C H H3C H O OH OH H O OH H O OH H OH H a mono methyl ether H OH H O HO CH3 O H H OH H H 3CO OH HO H H OH H H OH H O OH HO HO H H OH H H OH H O O CH3 HO HO H H OH H H OCH 3 H O OH H HO A OH O H HO H H3C H B OH OH OH H HO H H O OH H CH3 O C CH3 H O OH H A B C D D E Predict the product of the following reaction. β-D-glucopyranose H OH HO HO HO H H OH H CH3 O H CH3OH CH3OH H H OH HO HO HO H OH HO HO HO H H OH H CH3 O H H OH H H H OH HO H HO HO O H OH H H Why is the hydroxyl group on the anomeric carbon so reactive? β-D-glucopyranose H OH HO H HO HO CH3OH H OH HO HO HO H H HO HO HO H H H OH O CH3 CH3OH H OH HO HO HO H H H OH OH H H O H OH H H OH HO HO HO H H OH H CH3 O H H OH glycosidic bond H OH H α-D-glucopyranose Predict the initial product of the following reaction sequence. H OH H O HO HO H H HO H OH NEt3 CH3 I H 3O H2O Predict the initial product of the following reaction sequence. H OH H O HO HO H H CH3 I CH3 HO H H O HO HO H H HO B H OH OCH3 H H O H3CO H H CH3O H OCH3 H3CO H3CO H H CH3O H H H OCH3 H O HO H OH NEt3 CH3 I H 3O H2O H3CO H3CO H H CH3 O H H OCH3 H O OH H O H a mono methyl ether H OH H O HO CH3 O H H OH H H 3CO OH HO H H OH H H OH H O OH HO HO H H OH H H OH H O O CH3 HO HO H H OH H H OCH 3 H O OH fast slow H OCH3 HO CH3 H O Final product OH H3CO H3CO H H H H O OCH3 CH3O H HO HO H H HO A B C D Carbohydrates Carbohydrates are vicinal diols. Vicinal diols react with diols. acetone to form acetonides H OH HO H HO HO H O H OH H What is the first step in the mechanism of this reaction? A O H O H H OH HO H HO HO O H H OH H B H H O O H H O O H H O H O O H + H O O H O O H + O H O O O O H acetonide acetonide H O H O O H O H H O O O H O OH2 On a carbohydrate the –OH groups must be cis or cis acyclic. H OH HO H HO HO H O H OH H Which groups on the following glucose are cis? cis A B C + + + D+ E none none F all all β-D-glucopyranose H OH HO H HO HO H O H OH H vic diol must be cis or acyclic li H O O H + O H O O O O H vic diol must be cis or acyclic li H O O H + O H O O O O H acetonide H O H O O H acetonide H O H O O H O H H O O O H O OH2 O H H O O O H O OH2 Would glucose be predicted to react with acetone in the presence of acid? O O OH H H H O H O H O O H OH HO H HO HO H O H OH H How can this occur? O O OH H H H O H O H H OH HO H HO HO H O H OH H β-D-glucopyranose β-D-glucopyranose O O H OH HO H HO HO H O H OH H O O OH H O H H OH H HO H H O H O H OH O H OH OH What happens when glucose is treated with NaBH4? A NaBH4 does not react. H OH H O H H H OH H OH OH H H OH H H OH H H OH HO H HO HO H O H OH H NaBH4 H2O HO HO H What happens when glucose is treated with NaBH4? CH2OH H OH H OH OH CH2OH H OH H HO HO H H OH H O H H OH H NaBH4 OH HO HO H HO H O H OH H HO HO H H OH HO H O H OH H HO β-D-glucopyranose H OH HO H O H OH H H H β-D-glucopyranose B HO HO C HO HO 0.003% 0.003% D-glucitol (D(D-sorbitol) H3C H D H O H H H H H What happens when glucose is treated with oxidizing agents? β-D-glucopyranose H OH HO H HO HO H OH HO H HO HO H O H OH H H OH HO H OH HO H HO HO H OH H OH H O HO HO H H H OH OH H O H OH H What happens when glucose is treated with oxidizing agents? β-D-glucopyranose H OH HO H HO HO H HO H HO HO H O H OH H H OH HO H OH HO H HO HO H OH H OH H O HO HO H H H OH OH O H OH H Which functional group in glucose is is most sensitive to oxidation? H OH H HO HO H Ag+ Silver Mirror http://www.youtube.com/watch?v=hUX_cpFWNso H OH H O O OH O Ag0 64% H OH H HO HO H H O O OH O Ag0 Ag+ 64% H :NH3 (aq) H :NH3 (aq) 0.003% 0.003% D-gluconate D-gluconate 36% 36% H Ag α-D-glucopyranose H Ag α-D-glucopyranose ...
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This note was uploaded on 01/09/2011 for the course CHE 322 taught by Professor Staff during the Spring '08 term at SUNY Stony Brook.

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