A mechanism for the Smiles rearrangement reaction shown is to be given. Concept introduction: Smiles rearrangement is initiated by the nucleophilic attack of the lone pair of electrons on the N of the amino group on a carbon in the pyridine ring (made electron deficient by the electron attracting nitro group and electronegative N and O atoms). The cleavage of the five member ring formed and subsequent exchange of H + will lead to the formation of the rearranged product. To propose: A mechanism for the Smiles rearrangement reaction shown.

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Answer 1

Question

Chapter 16.SE, Problem 44MP

Interpretation Introduction

Interpretation:

A mechanism for the Smiles rearrangement reaction shown is to be given.

Concept introduction:

Smiles rearrangement is initiated by the nucleophilic attack of the lone pair of electrons on the N of the amino group on a carbon in the pyridine ring (made electron deficient by the electron attracting nitro group and electronegative N and O atoms). The cleavage of the five member ring formed and subsequent exchange of H⁺ will lead to the formation of the rearranged product.

To propose:

A mechanism for the Smiles rearrangement reaction shown.

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Answer 2

Question

Chapter 16.SE, Problem 44MP

Interpretation Introduction

Interpretation:

A mechanism for the Smiles rearrangement reaction shown is to be given.

Concept introduction:

Smiles rearrangement is initiated by the nucleophilic attack of the lone pair of electrons on the N of the amino group on a carbon in the pyridine ring (made electron deficient by the electron attracting nitro group and electronegative N and O atoms). The cleavage of the five member ring formed and subsequent exchange of H⁺ will lead to the formation of the rearranged product.

To propose:

A mechanism for the Smiles rearrangement reaction shown.

Expert Solution & Answer

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Check out a sample textbook solution

See solution

Answer 3

Question

Chapter 16.SE, Problem 44MP

Interpretation Introduction

Interpretation:

A mechanism for the Smiles rearrangement reaction shown is to be given.

Concept introduction:

Smiles rearrangement is initiated by the nucleophilic attack of the lone pair of electrons on the N of the amino group on a carbon in the pyridine ring (made electron deficient by the electron attracting nitro group and electronegative N and O atoms). The cleavage of the five member ring formed and subsequent exchange of H⁺ will lead to the formation of the rearranged product.

To propose:

A mechanism for the Smiles rearrangement reaction shown.

Expert Solution & Answer

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Check out a sample textbook solution

See solution

Answer 4

Question

Chapter 16.SE, Problem 44MP

Interpretation Introduction

Interpretation:

A mechanism for the Smiles rearrangement reaction shown is to be given.

Concept introduction:

Smiles rearrangement is initiated by the nucleophilic attack of the lone pair of electrons on the N of the amino group on a carbon in the pyridine ring (made electron deficient by the electron attracting nitro group and electronegative N and O atoms). The cleavage of the five member ring formed and subsequent exchange of H⁺ will lead to the formation of the rearranged product.

To propose:

A mechanism for the Smiles rearrangement reaction shown.

Expert Solution & Answer

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Check out a sample textbook solution

See solution

Answer 5

Chapter 16.SE, Problem 44MP

Interpretation Introduction

Interpretation:

A mechanism for the Smiles rearrangement reaction shown is to be given.

Concept introduction:

Smiles rearrangement is initiated by the nucleophilic attack of the lone pair of electrons on the N of the amino group on a carbon in the pyridine ring (made electron deficient by the electron attracting nitro group and electronegative N and O atoms). The cleavage of the five member ring formed and subsequent exchange of H⁺ will lead to the formation of the rearranged product.

To propose:

A mechanism for the Smiles rearrangement reaction shown.

Answer 6

Chapter 16.SE, Problem 44MP

Interpretation Introduction

Interpretation:

A mechanism for the Smiles rearrangement reaction shown is to be given.

Concept introduction:

Smiles rearrangement is initiated by the nucleophilic attack of the lone pair of electrons on the N of the amino group on a carbon in the pyridine ring (made electron deficient by the electron attracting nitro group and electronegative N and O atoms). The cleavage of the five member ring formed and subsequent exchange of H⁺ will lead to the formation of the rearranged product.

To propose:

A mechanism for the Smiles rearrangement reaction shown.

Answer 7

Chapter 16.SE, Problem 44MP

Interpretation Introduction

Interpretation:

A mechanism for the Smiles rearrangement reaction shown is to be given.

Concept introduction:

Smiles rearrangement is initiated by the nucleophilic attack of the lone pair of electrons on the N of the amino group on a carbon in the pyridine ring (made electron deficient by the electron attracting nitro group and electronegative N and O atoms). The cleavage of the five member ring formed and subsequent exchange of H⁺ will lead to the formation of the rearranged product.

To propose:

A mechanism for the Smiles rearrangement reaction shown.

Answer 8

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Answer 9

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Answer 10

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Answer 11

Ch. 16.1 - Prob. 1P Ch. 16.2 - Propose a mechanism for the electrophilic...Ch. 16.2 - How many products might be formed on chlorination...Ch. 16.2 - When benzene is treated with D2SÅª4. deuterium...Ch. 16.3 - Prob. 5P Ch. 16.3 - What is the major monosubstitution product from...Ch. 16.3 - Identify the carboxylic acid chloride that might...Ch. 16.4 - Rank the compounds in each of the following groups...Ch. 16.4 - Predict the major products of the following...Ch. 16.4 - Prob. 10P

Solution Summary: The author explains the mechanism for the Smiles rearrangement reaction shown.

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