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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Answer 1

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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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Answer 2

Question

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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Answer 3

Question

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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Answer 4

Question

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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Answer 5

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.

Answer 6

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.

Answer 7

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.

Answer 8

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Answer 9

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Answer 10

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Answer 11

Ch. 25 - Prob. 25.1P Ch. 25 - Prob. 25.2P Ch. 25 - Prob. 25.3P Ch. 25 - Prob. 25.4P Ch. 25 - Prob. 25.5P Ch. 25 - Prob. 25.6P Ch. 25 - Prob. 25.7P Ch. 25 - Prob. 25.8P Ch. 25 - Prob. 25.9P Ch. 25 - Prob. 25.10P

Solution Summary: The author explains the mechanism for the formation of a racemic mixture by heating the tetrabutylammonium salt of isotopically chiral

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Chapter 25 Solutions