(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.

Question

Want to see the full answer?

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.

Expert Solution & Answer

Want to see the full answer?

Check out a sample textbook solution

See solution

Students have asked these similar questions

Macmillan Learning X Chapter 12 HW - General, Organic, and E Ubiquinone, or coenzyme Q, is an electron acceptor in the electron transport chain. H3CO. CH3 (CH2CH=C-CH2)10H H3CO ubiquinone CH3 Modify the molecule so that it represents the reduced form of ubiquinone. You may need to add or remove atoms or bonds. Let the letter X represent the (CH2CH=C(CH3)CH2)10H group. Select / Draw Templates Groups More C 0 H о 0 Erase Q2Q

Draw the enolate anion and the ester that would be needed to make this product through a Claisen condensation reaction. ол

1. (10 points). Draw a stepwise detailed mechanism for the following reaction showing all the substitution and the elimination products formed. Label the type of the mechanism (SN1, SN2, E1 or E2). Show stereochemistry when applicable. Br CH3CH2OH H₂O 2. (10 points) 0 Br CH3O Na DMSO Draw the detailed mechanism showing ALL possible products formed including stereochemistry and Label mechanism as SN1, SN2, E1 or E2. Show stereochemistry when applicable.

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.

Expert Solution & Answer

Want to see the full answer?

Check out a sample textbook solution

See solution

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.

Expert Solution & Answer

Want to see the full answer?

Check out a sample textbook solution

See solution

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.

Expert Solution & Answer

Want to see the full answer?

Check out a sample textbook solution

See solution

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

Expert Solution & Answer

Answer 11

Expert Solution & Answer

Answer 12

Want to see the full answer?

Check out a sample textbook solution

See solution

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.

Want to see the full answer?

Chapter 11 Solutions