A mechanism for the following reaction of an α,β- unsaturated ester is to be proposed. Concept introduction: The steps involved in the conversion are i) Nucleophilic attack of the amine on the carbon on the α,β- unsaturated ester ii) Proton abstraction from the acid iii) A proton exchange from N to O iv) Another nucleophilic attack of N on the carbonyl carbon v)Another proton exchange from N to O vi) Loss of methanol and a proton. To propose: A mechanism for the reaction of an α,β- unsaturated ester with methylamine.

Question

Sonogashira coupling

Answer 1

Question

Chapter 19.SE, Problem 51MP

Interpretation Introduction

Interpretation:

A mechanism for the following reaction of an α,β- unsaturated ester is to be proposed.

Concept introduction:

The steps involved in the conversion are i) Nucleophilic attack of the amine on the carbon on the α,β- unsaturated ester ii) Proton abstraction from the acid iii) A proton exchange from N to O iv) Another nucleophilic attack of N on the carbonyl carbon v)Another proton exchange from N to O vi) Loss of methanol and a proton.

To propose:

A mechanism for the reaction of an α,β- unsaturated ester with methylamine.

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Sonogashira coupling

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Answer 2

Question

Chapter 19.SE, Problem 51MP

Interpretation Introduction

Interpretation:

A mechanism for the following reaction of an α,β- unsaturated ester is to be proposed.

Concept introduction:

The steps involved in the conversion are i) Nucleophilic attack of the amine on the carbon on the α,β- unsaturated ester ii) Proton abstraction from the acid iii) A proton exchange from N to O iv) Another nucleophilic attack of N on the carbonyl carbon v)Another proton exchange from N to O vi) Loss of methanol and a proton.

To propose:

A mechanism for the reaction of an α,β- unsaturated ester with methylamine.

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Answer 3

Question

Chapter 19.SE, Problem 51MP

Interpretation Introduction

Interpretation:

A mechanism for the following reaction of an α,β- unsaturated ester is to be proposed.

Concept introduction:

The steps involved in the conversion are i) Nucleophilic attack of the amine on the carbon on the α,β- unsaturated ester ii) Proton abstraction from the acid iii) A proton exchange from N to O iv) Another nucleophilic attack of N on the carbonyl carbon v)Another proton exchange from N to O vi) Loss of methanol and a proton.

To propose:

A mechanism for the reaction of an α,β- unsaturated ester with methylamine.

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Answer 4

Question

Chapter 19.SE, Problem 51MP

Interpretation Introduction

Interpretation:

A mechanism for the following reaction of an α,β- unsaturated ester is to be proposed.

Concept introduction:

The steps involved in the conversion are i) Nucleophilic attack of the amine on the carbon on the α,β- unsaturated ester ii) Proton abstraction from the acid iii) A proton exchange from N to O iv) Another nucleophilic attack of N on the carbonyl carbon v)Another proton exchange from N to O vi) Loss of methanol and a proton.

To propose:

A mechanism for the reaction of an α,β- unsaturated ester with methylamine.

Expert Solution & Answer

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Answer 5

Chapter 19.SE, Problem 51MP

Interpretation Introduction

Interpretation:

A mechanism for the following reaction of an α,β- unsaturated ester is to be proposed.

Concept introduction:

The steps involved in the conversion are i) Nucleophilic attack of the amine on the carbon on the α,β- unsaturated ester ii) Proton abstraction from the acid iii) A proton exchange from N to O iv) Another nucleophilic attack of N on the carbonyl carbon v)Another proton exchange from N to O vi) Loss of methanol and a proton.

To propose:

A mechanism for the reaction of an α,β- unsaturated ester with methylamine.

Answer 6

Chapter 19.SE, Problem 51MP

Interpretation Introduction

Interpretation:

A mechanism for the following reaction of an α,β- unsaturated ester is to be proposed.

Concept introduction:

The steps involved in the conversion are i) Nucleophilic attack of the amine on the carbon on the α,β- unsaturated ester ii) Proton abstraction from the acid iii) A proton exchange from N to O iv) Another nucleophilic attack of N on the carbonyl carbon v)Another proton exchange from N to O vi) Loss of methanol and a proton.

To propose:

A mechanism for the reaction of an α,β- unsaturated ester with methylamine.

Answer 7

Chapter 19.SE, Problem 51MP

Interpretation Introduction

Interpretation:

A mechanism for the following reaction of an α,β- unsaturated ester is to be proposed.

Concept introduction:

The steps involved in the conversion are i) Nucleophilic attack of the amine on the carbon on the α,β- unsaturated ester ii) Proton abstraction from the acid iii) A proton exchange from N to O iv) Another nucleophilic attack of N on the carbonyl carbon v)Another proton exchange from N to O vi) Loss of methanol and a proton.

To propose:

A mechanism for the reaction of an α,β- unsaturated ester with methylamine.

Answer 8

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Answer 19

Ch. 19.1 - Prob. 1P Ch. 19.1 - Draw structures corresponding to the following...Ch. 19.2 - Prob. 3P Ch. 19.2 - How would you carry out the following reactions?...Ch. 19.4 - Treatment of an aldehyde or ketone with cyanide...Ch. 19.4 - p-Nitrobenzaldehyde is more reactive toward...Ch. 19.5 - Prob. 7P Ch. 19.5 - The oxygen in water is primarily (99.8) 16O, but...Ch. 19.6 - Prob. 9P Ch. 19.8 - Show the products you would obtain by...

Solution Summary: The author proposes a mechanism for the reaction of an,- unsaturated ester with methylamine.

Chapter 19 Solutions