Basing your answers on the general mechanism for the first stage of acid-catalyzed

Chapter 23, Problem 23.40

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Basing your answers on the general mechanism for the first stage of acid-catalyzed acetal hydrolysis HO O O OH OH HO OCH3 OH OH OCH3 HO OH Compound A Compound B suggest reasonable explanations for the following observations: (a) Methyl -d-fructofuranoside (compound A) undergoes acid-catalyzed hydrolysis some 105 times faster than methyl -d-glucofuranoside (compound B). HO O O OH OH HO OCH3 OH OH OCH3 HO OH Compound A Compound B (b) The -methyl glucopyranoside of 2-deoxy-d-glucose (compound C) undergoes hydrolysis several thousand times faster than that of d-glucose (compound D). O HO HO OCH3 O HO HO OCH3 OH Compound C Compound D OH OH (c) Using Mechanism 23.2 as a guide, write a mechanism for the acid-catalyzed hydrolysis of compound D (methyl -d-glucopyranoside, shown in part b) to d-glucose. O HO HO OH OH Compound D H3O+ heat

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