A complete, detailed mechanism is to be drawn for the given reaction. Concept introduction: Alkyl amines with a β-hydrogen undergo an elimination reaction when treated with excess iodomethane followed by silver oxide and heating. Unlike most elimination reactions, this reaction gives the least substituted alkene , an anti-Zaitsev product. The reaction is called Hofmann elimination. The Amine functional group is alkylated to a quaternary ammonium ion, converting it into a bulky and good leaving group. If there are two hydrogens in β positions, then the one that gives the less substituted alkene is eliminated. This is because the leaving group is bulky, and the β-hydrogen on the less substituted carbon is in an anti-position in the most stable conformer. Formation of a more substituted alkene would generally require a less stable gauche conformer.

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Chapter 10, Problem 10.63P

Interpretation Introduction

Interpretation:

A complete, detailed mechanism is to be drawn for the given reaction.

Concept introduction:

Alkyl amines with a β-hydrogen undergo an elimination reaction when treated with excess iodomethane followed by silver oxide and heating. Unlike most elimination reactions, this reaction gives the least substituted alkene, an anti-Zaitsev product. The reaction is called Hofmann elimination.

The Amine functional group is alkylated to a quaternary ammonium ion, converting it into a bulky and good leaving group. If there are two hydrogens in β positions, then the one that gives the less substituted alkene is eliminated. This is because the leaving group is bulky, and the β-hydrogen on the less substituted carbon is in an anti-position in the most stable conformer. Formation of a more substituted alkene would generally require a less stable gauche conformer.

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Answer 2

Question

Chapter 10, Problem 10.63P

Interpretation Introduction

Interpretation:

A complete, detailed mechanism is to be drawn for the given reaction.

Concept introduction:

Alkyl amines with a β-hydrogen undergo an elimination reaction when treated with excess iodomethane followed by silver oxide and heating. Unlike most elimination reactions, this reaction gives the least substituted alkene, an anti-Zaitsev product. The reaction is called Hofmann elimination.

The Amine functional group is alkylated to a quaternary ammonium ion, converting it into a bulky and good leaving group. If there are two hydrogens in β positions, then the one that gives the less substituted alkene is eliminated. This is because the leaving group is bulky, and the β-hydrogen on the less substituted carbon is in an anti-position in the most stable conformer. Formation of a more substituted alkene would generally require a less stable gauche conformer.

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Answer 3

Question

Chapter 10, Problem 10.63P

Interpretation Introduction

Interpretation:

A complete, detailed mechanism is to be drawn for the given reaction.

Concept introduction:

Alkyl amines with a β-hydrogen undergo an elimination reaction when treated with excess iodomethane followed by silver oxide and heating. Unlike most elimination reactions, this reaction gives the least substituted alkene, an anti-Zaitsev product. The reaction is called Hofmann elimination.

The Amine functional group is alkylated to a quaternary ammonium ion, converting it into a bulky and good leaving group. If there are two hydrogens in β positions, then the one that gives the less substituted alkene is eliminated. This is because the leaving group is bulky, and the β-hydrogen on the less substituted carbon is in an anti-position in the most stable conformer. Formation of a more substituted alkene would generally require a less stable gauche conformer.

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Answer 4

Question

Chapter 10, Problem 10.63P

Interpretation Introduction

Interpretation:

A complete, detailed mechanism is to be drawn for the given reaction.

Concept introduction:

Alkyl amines with a β-hydrogen undergo an elimination reaction when treated with excess iodomethane followed by silver oxide and heating. Unlike most elimination reactions, this reaction gives the least substituted alkene, an anti-Zaitsev product. The reaction is called Hofmann elimination.

The Amine functional group is alkylated to a quaternary ammonium ion, converting it into a bulky and good leaving group. If there are two hydrogens in β positions, then the one that gives the less substituted alkene is eliminated. This is because the leaving group is bulky, and the β-hydrogen on the less substituted carbon is in an anti-position in the most stable conformer. Formation of a more substituted alkene would generally require a less stable gauche conformer.

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Answer 5

Chapter 10, Problem 10.63P

Interpretation Introduction

Interpretation:

A complete, detailed mechanism is to be drawn for the given reaction.

Concept introduction:

Alkyl amines with a β-hydrogen undergo an elimination reaction when treated with excess iodomethane followed by silver oxide and heating. Unlike most elimination reactions, this reaction gives the least substituted alkene, an anti-Zaitsev product. The reaction is called Hofmann elimination.

The Amine functional group is alkylated to a quaternary ammonium ion, converting it into a bulky and good leaving group. If there are two hydrogens in β positions, then the one that gives the less substituted alkene is eliminated. This is because the leaving group is bulky, and the β-hydrogen on the less substituted carbon is in an anti-position in the most stable conformer. Formation of a more substituted alkene would generally require a less stable gauche conformer.

Answer 6

Chapter 10, Problem 10.63P

Interpretation Introduction

Interpretation:

A complete, detailed mechanism is to be drawn for the given reaction.

Concept introduction:

Alkyl amines with a β-hydrogen undergo an elimination reaction when treated with excess iodomethane followed by silver oxide and heating. Unlike most elimination reactions, this reaction gives the least substituted alkene, an anti-Zaitsev product. The reaction is called Hofmann elimination.

The Amine functional group is alkylated to a quaternary ammonium ion, converting it into a bulky and good leaving group. If there are two hydrogens in β positions, then the one that gives the less substituted alkene is eliminated. This is because the leaving group is bulky, and the β-hydrogen on the less substituted carbon is in an anti-position in the most stable conformer. Formation of a more substituted alkene would generally require a less stable gauche conformer.

Answer 7

Chapter 10, Problem 10.63P

Interpretation Introduction

Interpretation:

A complete, detailed mechanism is to be drawn for the given reaction.

Concept introduction:

Alkyl amines with a β-hydrogen undergo an elimination reaction when treated with excess iodomethane followed by silver oxide and heating. Unlike most elimination reactions, this reaction gives the least substituted alkene, an anti-Zaitsev product. The reaction is called Hofmann elimination.

The Amine functional group is alkylated to a quaternary ammonium ion, converting it into a bulky and good leaving group. If there are two hydrogens in β positions, then the one that gives the less substituted alkene is eliminated. This is because the leaving group is bulky, and the β-hydrogen on the less substituted carbon is in an anti-position in the most stable conformer. Formation of a more substituted alkene would generally require a less stable gauche conformer.

Answer 8

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Answer 11

Ch. 10 - Prob. 10.1P Ch. 10 - Prob. 10.2P Ch. 10 - Prob. 10.3P Ch. 10 - Prob. 10.4P Ch. 10 - Prob. 10.5P Ch. 10 - Prob. 10.6P Ch. 10 - Prob. 10.7P Ch. 10 - Prob. 10.8P Ch. 10 - Prob. 10.9P Ch. 10 - Prob. 10.10P

Solution Summary: The author explains how amines can be used to synthesize alkenes or alkynes by treating them with an excess of iodomethane and aqueous silver oxide.

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