Dolbier HW Solutions 628

Dolbier HW Solutions 628 - 2,3,4 2,4,5 3,4,5 4,5,6 2,3,5...

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( b ) The carbocation formed from methyl b - D -glucopyranoside (compound D) is less stable than the one from its 2-deoxy analog (compound C) and is formed more slowly. It is destabilized by the electron-withdrawing inductive effect of the hydroxyl group at C-2. Faster: Slower: 25.31 D -Altrosan is a glycoside. The anomeric carbon the one with two oxygen substituents has an alkoxy group attached to it. Hydrolysis of D -altrosan follows the general mechanism for acetal hydrolysis. 25.32 Galactose has hydroxyl groups at carbons 2, 3, 4, 5, 6. Ten trimethyl ethers are therefore possible.
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Unformatted text preview: 2,3,4 2,4,5 3,4,5 4,5,6 2,3,5 2,4,6 3,4,6 2,3,6 2,5,6 3,5,6 1 H 1 HO HOCH 2 O HO OH H OH HO OH O O H OH HO OH O O H 1 H OH HO HOCH 2 OH O 1 HO HOCH 2 OH O OH H OH d-Altrose CHO CH 2 OH HO OH H OH H OH H H conformational change H 2 O 1 H OH HO HO HOCH 2 O OCH 3 H 1 H 2 CH 3 OH slow H 1 , fast OH HO HO HOCH 2 O 1 Less stable HO HO OH HOCH 2 O OCH 3 H D H HO HO HOCH 2 O OCH 3 H HO HO HOCH 2 O OCH 3 H 1 H 2 CH 3 OH slow H 1 , fast HO HO HOCH 2 O H 1 More stable C 722 CARBOHYDRATES...
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