A mechanism for the Pinner reaction shown, in which a nitrile is converted to an ester through an iminoester salt, is to be given using curved arrows to show the flow of electrons at each step, is to be proposed. Concept introduction: The Pinner reaction takes place through the steps given. i) Protonation of the nitrile ii) Nucleophilic attack of the alcohol on the protonated nitrile iii) proton transfer from oxygen to nitrogen iv) Nucleophilic attack by water on the protonated amine v) Elimination of a proton by water vi) Elimination of ammonia. To propose: A mechanism for the Pinner reaction shown, in which a nitrile is converted to an ester through an iminoester salt using curved arrows to show the flow of electrons at each step.

Question

Amino acids can be prepared by the reaction of alkyl halides with diethyl acetamidomalonate, followed by heating the initial alkylation product with aqueous HCl. The reaction to form alanine involves the following steps: Reaction of diethyl acetamidomalonate with sodium ethoxide to form enolate anion 1; The enolate anion acts as a nucleophile in an SN2 reaction with alkyl iodide 2 to form alkylated intermediate 2; Heating in the presence of aqueous acid hydrolyzes both the ester and the amide bonds, and induces decarboxylation to form alanine. Draw the structure of enolate anion 1.

Answer 1

Question

Chapter 20.SE, Problem 26MP

Interpretation Introduction

Interpretation:

A mechanism for the Pinner reaction shown, in which a nitrile is converted to an ester through an iminoester salt, is to be given using curved arrows to show the flow of electrons at each step, is to be proposed.

Concept introduction:

The Pinner reaction takes place through the steps given. i) Protonation of the nitrile ii) Nucleophilic attack of the alcohol on the protonated nitrile iii) proton transfer from oxygen to nitrogen iv) Nucleophilic attack by water on the protonated amine v) Elimination of a proton by water vi) Elimination of ammonia.

To propose:

A mechanism for the Pinner reaction shown, in which a nitrile is converted to an ester through an iminoester salt using curved arrows to show the flow of electrons at each step.

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Amino acids can be prepared by the reaction of alkyl halides with diethyl acetamidomalonate, followed by heating the initial alkylation product with aqueous HCl. The reaction to form alanine involves the following steps: Reaction of diethyl acetamidomalonate with sodium ethoxide to form enolate anion 1; The enolate anion acts as a nucleophile in an SN2 reaction with alkyl iodide 2 to form alkylated intermediate 2; Heating in the presence of aqueous acid hydrolyzes both the ester and the amide bonds, and induces decarboxylation to form alanine. Draw the structure of enolate anion 1.

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