The mechanism for the formation of a racemic mixture of tert-butyl phosphate by heating the tetrabutylammonium salt of isotopically chiral phenyl phosphate in the polar aprotic solvent acetonitrile containing excess of tert-butyl alcohol is to be drawn. Concept introduction: The tetrabutylammonium salt of isotopically chiral phenyl phosphate on heating in the polar aprotic solvent acetonitrile containing excess of tert-butyl alcohol first forms planar metaphosphate ion which is gets trapped by the solvent acetonitrile from either side which racemizes the phosphate by nucleophilic attack of tert-butyl alcohol.

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Chapter 25, Problem 25.31AP

Interpretation Introduction

Interpretation:

The mechanism for the formation of a racemic mixture of tert-butyl phosphate by heating the tetrabutylammonium salt of isotopically chiral phenyl phosphate in the polar aprotic solvent acetonitrile containing excess of tert-butyl alcohol is to be drawn.

Concept introduction:

The tetrabutylammonium salt of isotopically chiral phenyl phosphate on heating in the polar aprotic solvent acetonitrile containing excess of tert-butyl alcohol first forms planar metaphosphate ion which is gets trapped by the solvent acetonitrile from either side which racemizes the phosphate by nucleophilic attack of tert-butyl alcohol.

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