(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.

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Answer 1

Question

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.

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Questions 4 and 5

For a titration of 40.00 mL of 0.0500 M oxalic acid H2C2O4 with 0.1000 M KOH, calculate the pH at each of the following volume of KOH used in the titration: 1) before the titration begin;2) 15 mL; 3) 20 mL; 4) 25 mL; 5) 40 mL; 6) 50 mL. Ka1 = 5.90×10^-2, Ka2 = 6.50×10^-5 for oxalic acid.

Predict the major organic product(s), if any, of the following reactions. Assume all reagents are in excess unless otherwise indicated.

Answer 2

Question

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.

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Answer 3

Question

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.

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Answer 4

Question

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.

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Answer 5

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.

Answer 6

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.

Answer 7

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.

Answer 8

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.

Answer 9

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.

Answer 10

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.

Answer 11

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.

Answer 12

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Answer 13

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Answer 14

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Answer 15

Ch. 23 - Prob. 23.1P Ch. 23 - Prob. 23.2P Ch. 23 - Prob. 23.3P Ch. 23 - Prob. 23.4P Ch. 23 - Prob. 23.5P Ch. 23 - Prob. 23.6P Ch. 23 - Prob. 23.7P Ch. 23 - Prob. 23.8P Ch. 23 - Prob. 23.9P Ch. 23 - Prob. 23.10P

Solution Summary: The author explains the mechanism of Staudinger reaction for preparation of given compound.

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Chapter 23 Solutions