(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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19.78 Write the products of the following sequences of reactions. Refer to your reaction road- maps to see how the combined reactions allow you to "navigate" between the different functional groups. Note that you will need your old Chapters 6-11 and Chapters 15-18 roadmaps along with your new Chapter 19 roadmap for these. (a) 1. BHS 2. H₂O₂ 3. H₂CrO4 4. SOCI₂ (b) 1. Cl₂/hv 2. KOLBU 3. H₂O, catalytic H₂SO4 4. H₂CrO4 Reaction Roadmap An alkene 5. EtOH 6.0.5 Equiv. NaOEt/EtOH 7. Mild H₂O An alkane 1.0 2. (CH3)₂S 3. H₂CrO (d) (c) 4. Excess EtOH, catalytic H₂SO OH 4. Mild H₂O* 5.0.5 Equiv. NaOEt/EtOH An alkene 6. Mild H₂O* A carboxylic acid 7. Mild H₂O* 1. SOC₁₂ 2. EtOH 3.0.5 Equiv. NaOEt/E:OH 5.1.0 Equiv. NaOEt 6. NH₂ (e) 1. 0.5 Equiv. NaOEt/EtOH 2. Mild H₂O* Br (f) i H An aldehyde 1. Catalytic NaOE/EtOH 2. H₂O*, heat 3. (CH,CH₂)₂Culi 4. Mild H₂O* 5.1.0 Equiv. LDA Br An ester 4. NaOH, H₂O 5. Mild H₂O* 6. Heat 7. MgBr 8. Mild H₂O* 7. Mild H₂O+

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