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

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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Students have asked these similar questions

(a) Which is more reactive towards Electrophilic aromatic substitution (EAS)? (b) Which of the following is a a meta-substituted compound? (c) Which is the least reactive towards Electrophilic aromatic substitution (EAS)? (d) Which is an ortho-substituted compound?

(a) Which is the correct structure of the alkyl halide substrate? (b) Which is the correct structure of the nucleophile?

From the given structures which is(a) an acid halide? (b) a secondary amide (c) an aldehyde incapable of self-aldol consensation?

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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See solution

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