(a) Interpretation: The curved arrow mechanism for the given rearrangement reaction is to be shown. Concept Introduction: Benzylic protons are very acidic in nature as the conjugate base formed by the acid is resonance stabilized. Even a mild base can also abstract hydrogen ion. Intramolecular nucleophilic addition reaction takes place in those compounds in which nucleophile and electrophile both are present in the same compound.

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Answer 1

Question

Chapter 23, Problem 23.74AP

Interpretation Introduction

(a)

Interpretation:

The curved arrow mechanism for the given rearrangement reaction is to be shown.

Concept Introduction:

Benzylic protons are very acidic in nature as the conjugate base formed by the acid is resonance stabilized. Even a mild base can also abstract hydrogen ion. Intramolecular nucleophilic addition reaction takes place in those compounds in which nucleophile and electrophile both are present in the same compound.

Interpretation Introduction

(b)

Interpretation:

The curved arrow mechanism for the given rearrangement reaction is to be shown.

Concept Introduction:

Bromosuccinimide is a source of bromine radical. It can undergo various reactions. Nucleophilic addition reaction uses a nucleophile such as hydroxide ion which attacks at the electrophilic centre of the given compound to form nucleophilic addition product.

Interpretation Introduction

(c)

Interpretation:

The curved arrow mechanism for the given rearrangement reaction is to be shown.

Concept Introduction:

Acyl azide is heated in an inert solvent to form isocyanate with loss of nitrogen as by product. This reaction is known as Curtius rearrangement reaction. Isocyanate product of the rearrangement can be converted into amine by hydration in either an acid or base.

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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?

(i) Explain why a high reaction temperature favours elimination reactions, instead of substitution reactions. (ii) Explain why polar aprotic solvents favour Sn2 reaction but not favour SN1 reaction.

Consider the tetracyclic compound with rings labeled A–D. (a) Which ring is the most reactive in electrophilic aromatic substitution? (b) Which ring is the least reactive in electrophilic aromatic substitution?

Answer 2

Question

Chapter 23, Problem 23.74AP

Interpretation Introduction

(a)

Interpretation:

The curved arrow mechanism for the given rearrangement reaction is to be shown.

Concept Introduction:

Benzylic protons are very acidic in nature as the conjugate base formed by the acid is resonance stabilized. Even a mild base can also abstract hydrogen ion. Intramolecular nucleophilic addition reaction takes place in those compounds in which nucleophile and electrophile both are present in the same compound.

Interpretation Introduction

(b)

Interpretation:

The curved arrow mechanism for the given rearrangement reaction is to be shown.

Concept Introduction:

Bromosuccinimide is a source of bromine radical. It can undergo various reactions. Nucleophilic addition reaction uses a nucleophile such as hydroxide ion which attacks at the electrophilic centre of the given compound to form nucleophilic addition product.

Interpretation Introduction

(c)

Interpretation:

The curved arrow mechanism for the given rearrangement reaction is to be shown.

Concept Introduction:

Acyl azide is heated in an inert solvent to form isocyanate with loss of nitrogen as by product. This reaction is known as Curtius rearrangement reaction. Isocyanate product of the rearrangement can be converted into amine by hydration in either an acid or base.

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Answer 3

Question

Chapter 23, Problem 23.74AP

Interpretation Introduction

(a)

Interpretation:

The curved arrow mechanism for the given rearrangement reaction is to be shown.

Concept Introduction:

Benzylic protons are very acidic in nature as the conjugate base formed by the acid is resonance stabilized. Even a mild base can also abstract hydrogen ion. Intramolecular nucleophilic addition reaction takes place in those compounds in which nucleophile and electrophile both are present in the same compound.

Interpretation Introduction

(b)

Interpretation:

The curved arrow mechanism for the given rearrangement reaction is to be shown.

Concept Introduction:

Bromosuccinimide is a source of bromine radical. It can undergo various reactions. Nucleophilic addition reaction uses a nucleophile such as hydroxide ion which attacks at the electrophilic centre of the given compound to form nucleophilic addition product.

Interpretation Introduction

(c)

Interpretation:

The curved arrow mechanism for the given rearrangement reaction is to be shown.

Concept Introduction:

Acyl azide is heated in an inert solvent to form isocyanate with loss of nitrogen as by product. This reaction is known as Curtius rearrangement reaction. Isocyanate product of the rearrangement can be converted into amine by hydration in either an acid or base.

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Answer 4

Question

Chapter 23, Problem 23.74AP

Interpretation Introduction

(a)

Interpretation:

The curved arrow mechanism for the given rearrangement reaction is to be shown.

Concept Introduction:

Benzylic protons are very acidic in nature as the conjugate base formed by the acid is resonance stabilized. Even a mild base can also abstract hydrogen ion. Intramolecular nucleophilic addition reaction takes place in those compounds in which nucleophile and electrophile both are present in the same compound.

Interpretation Introduction

(b)

Interpretation:

The curved arrow mechanism for the given rearrangement reaction is to be shown.

Concept Introduction:

Bromosuccinimide is a source of bromine radical. It can undergo various reactions. Nucleophilic addition reaction uses a nucleophile such as hydroxide ion which attacks at the electrophilic centre of the given compound to form nucleophilic addition product.

Interpretation Introduction

(c)

Interpretation:

The curved arrow mechanism for the given rearrangement reaction is to be shown.

Concept Introduction:

Acyl azide is heated in an inert solvent to form isocyanate with loss of nitrogen as by product. This reaction is known as Curtius rearrangement reaction. Isocyanate product of the rearrangement can be converted into amine by hydration in either an acid or base.

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Answer 5

Chapter 23, Problem 23.74AP

Interpretation Introduction

(a)

Interpretation:

The curved arrow mechanism for the given rearrangement reaction is to be shown.

Concept Introduction:

Benzylic protons are very acidic in nature as the conjugate base formed by the acid is resonance stabilized. Even a mild base can also abstract hydrogen ion. Intramolecular nucleophilic addition reaction takes place in those compounds in which nucleophile and electrophile both are present in the same compound.

Interpretation Introduction

(b)

Interpretation:

The curved arrow mechanism for the given rearrangement reaction is to be shown.

Concept Introduction:

Bromosuccinimide is a source of bromine radical. It can undergo various reactions. Nucleophilic addition reaction uses a nucleophile such as hydroxide ion which attacks at the electrophilic centre of the given compound to form nucleophilic addition product.

Interpretation Introduction

(c)

Interpretation:

The curved arrow mechanism for the given rearrangement reaction is to be shown.

Concept Introduction:

Acyl azide is heated in an inert solvent to form isocyanate with loss of nitrogen as by product. This reaction is known as Curtius rearrangement reaction. Isocyanate product of the rearrangement can be converted into amine by hydration in either an acid or base.

Answer 6

Chapter 23, Problem 23.74AP

Interpretation Introduction

(a)

Interpretation:

The curved arrow mechanism for the given rearrangement reaction is to be shown.

Concept Introduction:

Benzylic protons are very acidic in nature as the conjugate base formed by the acid is resonance stabilized. Even a mild base can also abstract hydrogen ion. Intramolecular nucleophilic addition reaction takes place in those compounds in which nucleophile and electrophile both are present in the same compound.

Answer 7

Chapter 23, Problem 23.74AP

Interpretation Introduction

(a)

Interpretation:

The curved arrow mechanism for the given rearrangement reaction is to be shown.

Concept Introduction:

Benzylic protons are very acidic in nature as the conjugate base formed by the acid is resonance stabilized. Even a mild base can also abstract hydrogen ion. Intramolecular nucleophilic addition reaction takes place in those compounds in which nucleophile and electrophile both are present in the same compound.

Answer 8

Interpretation Introduction

(b)

Interpretation:

The curved arrow mechanism for the given rearrangement reaction is to be shown.

Concept Introduction:

Bromosuccinimide is a source of bromine radical. It can undergo various reactions. Nucleophilic addition reaction uses a nucleophile such as hydroxide ion which attacks at the electrophilic centre of the given compound to form nucleophilic addition product.

Answer 9

Interpretation Introduction

(b)

Interpretation:

The curved arrow mechanism for the given rearrangement reaction is to be shown.

Concept Introduction:

Bromosuccinimide is a source of bromine radical. It can undergo various reactions. Nucleophilic addition reaction uses a nucleophile such as hydroxide ion which attacks at the electrophilic centre of the given compound to form nucleophilic addition product.

Answer 10

Interpretation Introduction

(c)

Interpretation:

The curved arrow mechanism for the given rearrangement reaction is to be shown.

Concept Introduction:

Acyl azide is heated in an inert solvent to form isocyanate with loss of nitrogen as by product. This reaction is known as Curtius rearrangement reaction. Isocyanate product of the rearrangement can be converted into amine by hydration in either an acid or base.

Answer 11

Interpretation Introduction

(c)

Interpretation:

The curved arrow mechanism for the given rearrangement reaction is to be shown.

Concept Introduction:

Acyl azide is heated in an inert solvent to form isocyanate with loss of nitrogen as by product. This reaction is known as Curtius rearrangement reaction. Isocyanate product of the rearrangement can be converted into amine by hydration in either an acid or base.

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 curved arrow mechanism for the given rearrangement reaction.

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Chapter 23 Solutions