Organic Chemistry
Organic Chemistry
9th Edition
ISBN: 9781305080485
Author: John E. McMurry
Publisher: Cengage Learning
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Chapter 31.SE, Problem 18MP
Interpretation Introduction

Interpretation:

Propose the mechanism for the formation of polymeric resin by the reaction of polystyrene with n-(hydroxymethyl) pthalimide and triflouromethanesulphonic acid followed by the reaction with hydrazine.

Concept introduction:

In the Merrifield solid-phase method, peptide synthesis is carried out with the growing amino acid chain covalently bonded to small beads of a polymer resin, rather than in solution.

SN2 reaction is a type of reaction mechanism in which one bond is broken and one bond is formed simultaneously. In first step nucleophilic substitution reaction takes place. Since two reacting species are involved in the slow (rate-determining) step, this leads to the term substitution nucleophilic (bi-molecular) or SN2.

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A variation of the acetamidomalonate synthesis can be used to synthesize serine. The process involves the following steps: Ethoxide ion deprotonates diethyl acetamidomalonate, forming enolate anion 1; Enolate anion 1 makes a nucleophilic attack on formaldehyde, forming tetrahedral intermediate 2; Protonation of the oxyanion forms alcohol 3; Acid hydrolysis yields dicarboxyamino alcohol 4; Decarboxylation leads to the final amino acid. Write out the mechanism on a separate sheet of paper, and then draw the structure of tetrahedral intermediate 2. You do not have to consider stereochemistry. You do not have to explicitly draw H atoms. Do not include lone pairs in your answer. They will not be considered in the grading. Draw carboxyl and amino groups in their uncharged forms.
A variation of the acetamidomalonate synthesis can be used to synthesize threonine. The process involves the following steps: Ethoxide ion deprotonates diethyl acetamidomalonate, forming enolate anion 1; Enolate anion 1 makes a nucleophilic attack on acetaldehyde, forming tetrahedral intermediate 2; Protonation of the oxyanion forms alcohol 3; Acid hydrolysis yields dicarboxyamino alcohol 4; Decarboxylation leads to the final amino acid. Write out the mechanism on a separate sheet of paper, and then draw the structure of enolate anion 1.
Synthesize the o-form of amino benzoic acid from benzene.
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