Organic Chemistry
Organic Chemistry
12th Edition
ISBN: 9781118875766
Author: T. W. Graham Solomons, Craig B. Fryhle, Scott A. Snyder
Publisher: WILEY
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Chapter 24, Problem 11PP
Interpretation Introduction

Interpretation:

The classes of reactions are involved in the cleavage of the Fmoc group with piperidine,

leading to the unprotected amino acid and the fluorene byproduct are to be determined. The mechanisms for these reactions are to be written.

Concept introduction:

The 9-fluorenylmethyloxycarbonyl protecting group (Fmoc) is a protecting group particularly used in peptide chemistry. It protects the amino group of the first amino acid. It is stable under low pH, but can be removed under high pH. The solution of 20% piperidine in DMF is usually employed.

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26. (i) Why is the ester formation of alcohols and acid chlorides done in a weakly basic solution like pyrmidine? (ii) Why is this setup not viable for alcohols and carboxylic acids to form esters? pyrimidine deprotonates the alcohol; the alkoxide ion forms pyrimidine deprotonates the alcohol; the carboxylate ion forms pyrimidine deprotonates the tetrahedral intermediate; the alkoxide ion forms pyrimidine deprotonates the tetrahedral intermediate; the carboxylate ion forms
PRACTICE PROBLEM 24.12 Show all steps in the synthesis of GVA using the tert-butyloxycarbonyl (Boc) group as a protecting group.
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