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

Organic Chemistry, | 9th Edition | ISBN: 9780073402741 | Authors: Francis A Carey Dr., Robert M. Giuliano ISBN: 9780073402741 326

Solution for problem 23.40 Chapter 23

Organic Chemistry, | 9th Edition

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Organic Chemistry, | 9th Edition | ISBN: 9780073402741 | Authors: Francis A Carey Dr., Robert M. Giuliano

Organic Chemistry, | 9th Edition

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Problem 23.40

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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Introduction to Organic Chemistry What are hydrocarbons Hydrocarbons: Molecules that contain carbon and hydrogen *Simplest organic molecules Organic Chemistry: Study of hydrocarbons and their derivatives Carbon Bonding: Covalent bonding following the octet rule -Saturated: All single bonds -Unsaturated:...

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Chapter 23, Problem 23.40 is Solved
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Textbook: Organic Chemistry,
Edition: 9
Author: Francis A Carey Dr., Robert M. Giuliano
ISBN: 9780073402741

Organic Chemistry, was written by and is associated to the ISBN: 9780073402741. This textbook survival guide was created for the textbook: Organic Chemistry, , edition: 9. The answer to “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” is broken down into a number of easy to follow steps, and 140 words. The full step-by-step solution to problem: 23.40 from chapter: 23 was answered by , our top Chemistry solution expert on 03/05/18, 08:00PM. Since the solution to 23.40 from 23 chapter was answered, more than 218 students have viewed the full step-by-step answer. This full solution covers the following key subjects: . This expansive textbook survival guide covers 375 chapters, and 1430 solutions.

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