(a) Interpretation: The complete, detailed mechanism of the given reaction is to be drawn, and the major product is to be predicted. Concept introduction: Like carbon-carbon double bond of an alkene , the carbon-carbon triple bond of an alkyne also undergoes electrophilic addition reaction with a strong Bronsted acid. In the first step, a proton is added to a carbon-carbon triple bond to form a vinylic cation, which is then coordinated with the respective anion formed in the first step. An alkene is formed, which further shows electrophilic addition reaction with Bronsted acid to form an alkane as the final product. When alkynes are treated with excess Bronsted acid, like hydrogen halide, the geminal dihalide is formed as the major product.

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Answer 1

Question

Chapter 11, Problem 11.13P

Interpretation Introduction

(a)

Interpretation:

The complete, detailed mechanism of the given reaction is to be drawn, and the major product is to be predicted.

Concept introduction:

Like carbon-carbon double bond of an alkene, the carbon-carbon triple bond of an alkyne also undergoes electrophilic addition reaction with a strong Bronsted acid. In the first step, a proton is added to a carbon-carbon triple bond to form a vinylic cation, which is then coordinated with the respective anion formed in the first step. An alkene is formed, which further shows electrophilic addition reaction with Bronsted acid to form an alkane as the final product. When alkynes are treated with excess Bronsted acid, like hydrogen halide, the geminal dihalide is formed as the major product.

Interpretation Introduction

(b)

Interpretation:

The complete, detailed mechanism of the given reaction is to be drawn, and the major product is to be predicted.

Concept introduction:

Like carbon-carbon double bond of an alkene, the carbon-carbon triple bond of an alkyne also undergoes electrophilic addition reaction with a strong Bronsted acid. In the first step, a proton is added to a carbon-carbon triple bond to form a vinylic cation, which is then coordinated with the respective anion formed in the first step. An alkene is formed, which further shows electrophilic addition reaction with Bronsted acid to form an alkane as the final product. When alkynes are treated with excess Bronsted acid, like hydrogen halide, the geminal dihalide is formed as the major product.

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If a reaction occurs, what would be the major products? Please include a detailed explanation as well as a drawing showing how the reaction occurs and what the final product is.

Answer 2

Question

Chapter 11, Problem 11.13P

Interpretation Introduction

(a)

Interpretation:

The complete, detailed mechanism of the given reaction is to be drawn, and the major product is to be predicted.

Concept introduction:

Like carbon-carbon double bond of an alkene, the carbon-carbon triple bond of an alkyne also undergoes electrophilic addition reaction with a strong Bronsted acid. In the first step, a proton is added to a carbon-carbon triple bond to form a vinylic cation, which is then coordinated with the respective anion formed in the first step. An alkene is formed, which further shows electrophilic addition reaction with Bronsted acid to form an alkane as the final product. When alkynes are treated with excess Bronsted acid, like hydrogen halide, the geminal dihalide is formed as the major product.

Interpretation Introduction

(b)

Interpretation:

The complete, detailed mechanism of the given reaction is to be drawn, and the major product is to be predicted.

Concept introduction:

Like carbon-carbon double bond of an alkene, the carbon-carbon triple bond of an alkyne also undergoes electrophilic addition reaction with a strong Bronsted acid. In the first step, a proton is added to a carbon-carbon triple bond to form a vinylic cation, which is then coordinated with the respective anion formed in the first step. An alkene is formed, which further shows electrophilic addition reaction with Bronsted acid to form an alkane as the final product. When alkynes are treated with excess Bronsted acid, like hydrogen halide, the geminal dihalide is formed as the major product.

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Answer 3

Question

Chapter 11, Problem 11.13P

Interpretation Introduction

(a)

Interpretation:

The complete, detailed mechanism of the given reaction is to be drawn, and the major product is to be predicted.

Concept introduction:

Like carbon-carbon double bond of an alkene, the carbon-carbon triple bond of an alkyne also undergoes electrophilic addition reaction with a strong Bronsted acid. In the first step, a proton is added to a carbon-carbon triple bond to form a vinylic cation, which is then coordinated with the respective anion formed in the first step. An alkene is formed, which further shows electrophilic addition reaction with Bronsted acid to form an alkane as the final product. When alkynes are treated with excess Bronsted acid, like hydrogen halide, the geminal dihalide is formed as the major product.

Interpretation Introduction

(b)

Interpretation:

The complete, detailed mechanism of the given reaction is to be drawn, and the major product is to be predicted.

Concept introduction:

Like carbon-carbon double bond of an alkene, the carbon-carbon triple bond of an alkyne also undergoes electrophilic addition reaction with a strong Bronsted acid. In the first step, a proton is added to a carbon-carbon triple bond to form a vinylic cation, which is then coordinated with the respective anion formed in the first step. An alkene is formed, which further shows electrophilic addition reaction with Bronsted acid to form an alkane as the final product. When alkynes are treated with excess Bronsted acid, like hydrogen halide, the geminal dihalide is formed as the major product.

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Answer 4

Question

Chapter 11, Problem 11.13P

Interpretation Introduction

(a)

Interpretation:

The complete, detailed mechanism of the given reaction is to be drawn, and the major product is to be predicted.

Concept introduction:

Like carbon-carbon double bond of an alkene, the carbon-carbon triple bond of an alkyne also undergoes electrophilic addition reaction with a strong Bronsted acid. In the first step, a proton is added to a carbon-carbon triple bond to form a vinylic cation, which is then coordinated with the respective anion formed in the first step. An alkene is formed, which further shows electrophilic addition reaction with Bronsted acid to form an alkane as the final product. When alkynes are treated with excess Bronsted acid, like hydrogen halide, the geminal dihalide is formed as the major product.

Interpretation Introduction

(b)

Interpretation:

The complete, detailed mechanism of the given reaction is to be drawn, and the major product is to be predicted.

Concept introduction:

Like carbon-carbon double bond of an alkene, the carbon-carbon triple bond of an alkyne also undergoes electrophilic addition reaction with a strong Bronsted acid. In the first step, a proton is added to a carbon-carbon triple bond to form a vinylic cation, which is then coordinated with the respective anion formed in the first step. An alkene is formed, which further shows electrophilic addition reaction with Bronsted acid to form an alkane as the final product. When alkynes are treated with excess Bronsted acid, like hydrogen halide, the geminal dihalide is formed as the major product.

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Answer 5

Chapter 11, Problem 11.13P

Interpretation Introduction

(a)

Interpretation:

The complete, detailed mechanism of the given reaction is to be drawn, and the major product is to be predicted.

Concept introduction:

Like carbon-carbon double bond of an alkene, the carbon-carbon triple bond of an alkyne also undergoes electrophilic addition reaction with a strong Bronsted acid. In the first step, a proton is added to a carbon-carbon triple bond to form a vinylic cation, which is then coordinated with the respective anion formed in the first step. An alkene is formed, which further shows electrophilic addition reaction with Bronsted acid to form an alkane as the final product. When alkynes are treated with excess Bronsted acid, like hydrogen halide, the geminal dihalide is formed as the major product.

Interpretation Introduction

(b)

Interpretation:

The complete, detailed mechanism of the given reaction is to be drawn, and the major product is to be predicted.

Concept introduction:

Like carbon-carbon double bond of an alkene, the carbon-carbon triple bond of an alkyne also undergoes electrophilic addition reaction with a strong Bronsted acid. In the first step, a proton is added to a carbon-carbon triple bond to form a vinylic cation, which is then coordinated with the respective anion formed in the first step. An alkene is formed, which further shows electrophilic addition reaction with Bronsted acid to form an alkane as the final product. When alkynes are treated with excess Bronsted acid, like hydrogen halide, the geminal dihalide is formed as the major product.

Answer 6

Chapter 11, Problem 11.13P

Interpretation Introduction

(a)

Interpretation:

The complete, detailed mechanism of the given reaction is to be drawn, and the major product is to be predicted.

Concept introduction:

Like carbon-carbon double bond of an alkene, the carbon-carbon triple bond of an alkyne also undergoes electrophilic addition reaction with a strong Bronsted acid. In the first step, a proton is added to a carbon-carbon triple bond to form a vinylic cation, which is then coordinated with the respective anion formed in the first step. An alkene is formed, which further shows electrophilic addition reaction with Bronsted acid to form an alkane as the final product. When alkynes are treated with excess Bronsted acid, like hydrogen halide, the geminal dihalide is formed as the major product.

Answer 7

Chapter 11, Problem 11.13P

Interpretation Introduction

(a)

Interpretation:

The complete, detailed mechanism of the given reaction is to be drawn, and the major product is to be predicted.

Concept introduction:

Like carbon-carbon double bond of an alkene, the carbon-carbon triple bond of an alkyne also undergoes electrophilic addition reaction with a strong Bronsted acid. In the first step, a proton is added to a carbon-carbon triple bond to form a vinylic cation, which is then coordinated with the respective anion formed in the first step. An alkene is formed, which further shows electrophilic addition reaction with Bronsted acid to form an alkane as the final product. When alkynes are treated with excess Bronsted acid, like hydrogen halide, the geminal dihalide is formed as the major product.

Answer 8

Interpretation Introduction

(b)

Interpretation:

The complete, detailed mechanism of the given reaction is to be drawn, and the major product is to be predicted.

Concept introduction:

Like carbon-carbon double bond of an alkene, the carbon-carbon triple bond of an alkyne also undergoes electrophilic addition reaction with a strong Bronsted acid. In the first step, a proton is added to a carbon-carbon triple bond to form a vinylic cation, which is then coordinated with the respective anion formed in the first step. An alkene is formed, which further shows electrophilic addition reaction with Bronsted acid to form an alkane as the final product. When alkynes are treated with excess Bronsted acid, like hydrogen halide, the geminal dihalide is formed as the major product.

Answer 9

Interpretation Introduction

(b)

Interpretation:

The complete, detailed mechanism of the given reaction is to be drawn, and the major product is to be predicted.

Concept introduction:

Like carbon-carbon double bond of an alkene, the carbon-carbon triple bond of an alkyne also undergoes electrophilic addition reaction with a strong Bronsted acid. In the first step, a proton is added to a carbon-carbon triple bond to form a vinylic cation, which is then coordinated with the respective anion formed in the first step. An alkene is formed, which further shows electrophilic addition reaction with Bronsted acid to form an alkane as the final product. When alkynes are treated with excess Bronsted acid, like hydrogen halide, the geminal dihalide is formed as the major product.

Answer 10

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Answer 13

Ch. 11 - Prob. 11.1P Ch. 11 - Prob. 11.2P Ch. 11 - Prob. 11.3P Ch. 11 - Prob. 11.4P Ch. 11 - Prob. 11.5P Ch. 11 - Prob. 11.6P Ch. 11 - Prob. 11.7P Ch. 11 - Prob. 11.8P Ch. 11 - Prob. 11.9P Ch. 11 - Prob. 11.10P

Solution Summary: The author explains the electrophilic addition reaction of a Bronsted acid with the carbon-carbon triple bond of an alkyne.

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Chapter 11 Solutions