Chapter 23, Problem 23.81AP

Interpretation Introduction

(a)

Interpretation:

The mechanism of Staudinger reaction for preparation of given compound is to be stated.

Concept Introduction:

Reaction of alkyl halide with sodium azide gives alkyl azide. The alkyl azide reacts with triphenyl phosphine to form phosphazide. Phosphazide undergoes rearrangement reaction to form iminophosphorane. In presence of water, iminophosphorane hydrolyses to give triphenylphosphine oxide and a primary amine. This reaction is known as the Staudinger reaction.

Interpretation Introduction

(b)

Interpretation:

The mechanism for conversion of intermediate to probe labeled protein product is to be shown.

Concept Introduction:

Reaction of alkyl halide with sodium azide gives alkyl azide. The alkyl azide reacts with triphenyl phosphine to form phosphazide. Phosphazide undergoes rearrangement reaction to form iminophosphorane. In presence of water iminophosphorane hydrolysed to give triphenylphosphine oxide and a primary amine. This reaction is known as the Staudinger reaction.

Interpretation Introduction

(c)

Interpretation:

In absence of methyl ester functional group, the product formed in the presence of water is to be stated.

Concept Introduction:

Reaction of alkyl halide with sodium azide gives alkyl azide. The alkyl azide reacts with triphenyl phosphine to form phosphazide. Phosphazide undergoes rearrangement reaction to form iminophosphorane. In presence of water iminophosphorane hydrolysed to give triphenylphosphine oxide and a primary amine. This reaction is known as the Staudinger reaction.