Organic Chemistry Plus Masteringchemistry With Pearson Etext, Global Edition
Organic Chemistry Plus Masteringchemistry With Pearson Etext, Global Edition
9th Edition
ISBN: 9781292151229
Author: Wade, LeRoy G.
Publisher: PEARSON
Question
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Chapter 26.7D, Problem 26.18P
Interpretation Introduction

Interpretation:

A mechanism for the reaction of phenyl isocyanate and ethanol is to be proposed.

Concept Introduction:

Phenyl isocyanate reacts with ethanol to form ethyl-N-phenylcarbamate. The isocyanate group of phenyl isocyanate reacts with hydroxyl group of ethanol and leads to the formation of single product.

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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.
Propose a mechanism for the reaction of phenyl isocyanate with ethanol.
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