(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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1) a) Give the dominant Intermolecular Force (IMF) in a sample of each of the following compounds. Please show your work. (8) SF2, CH,OH, C₂H₂ b) Based on your answers given above, list the compounds in order of their Boiling Point from low to high. (8)

19.78 Write the products of the following sequences of reactions. Refer to your reaction road- maps to see how the combined reactions allow you to "navigate" between the different functional groups. Note that you will need your old Chapters 6-11 and Chapters 15-18 roadmaps along with your new Chapter 19 roadmap for these. (a) 1. BHS 2. H₂O₂ 3. H₂CrO4 4. SOCI₂ (b) 1. Cl₂/hv 2. KOLBU 3. H₂O, catalytic H₂SO4 4. H₂CrO4 Reaction Roadmap An alkene 5. EtOH 6.0.5 Equiv. NaOEt/EtOH 7. Mild H₂O An alkane 1.0 2. (CH3)₂S 3. H₂CrO (d) (c) 4. Excess EtOH, catalytic H₂SO OH 4. Mild H₂O* 5.0.5 Equiv. NaOEt/EtOH An alkene 6. Mild H₂O* A carboxylic acid 7. Mild H₂O* 1. SOC₁₂ 2. EtOH 3.0.5 Equiv. NaOEt/E:OH 5.1.0 Equiv. NaOEt 6. NH₂ (e) 1. 0.5 Equiv. NaOEt/EtOH 2. Mild H₂O* Br (f) i H An aldehyde 1. Catalytic NaOE/EtOH 2. H₂O*, heat 3. (CH,CH₂)₂Culi 4. Mild H₂O* 5.1.0 Equiv. LDA Br An ester 4. NaOH, H₂O 5. Mild H₂O* 6. Heat 7. MgBr 8. Mild H₂O* 7. Mild H₂O+

Li+ is a hard acid. With this in mind, which if the following compounds should be most soluble in water? Group of answer choices LiBr LiI LiF LiCl

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 11

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Answer 12

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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