(a) Interpretation: How to synthesize the given compound from an alkyne is to be described. Concept introduction: The carbon-carbon triple bond in terminal alkynes is electron rich and thus undergoes electrophilic addition reaction with a strong Bronsted acid such as hydrogen halide. Addition of two equivalents of hydrogen halide to a terminal alkyne produces a geminal dihalide, in which both the halide atoms are on the same carbon atom. The regioselectivity is in accordance with the Markovnikov’s rule. The hydrogen halide adds twice to generate the geminal dihalide. If hydrogen chloride is used as a reagent, the reaction goes through vinylic carbocation intermediate as the chlorine atom will stabilize the positive charge on the carbon atom through resonance. The alkyne must be symmetric to avoid producing a mixture of isomers.

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Answer 1

Question

Chapter 11, Problem 11.14P

Interpretation Introduction

(a)

Interpretation:

How to synthesize the given compound from an alkyne is to be described.

Concept introduction:

The carbon-carbon triple bond in terminal alkynes is electron rich and thus undergoes electrophilic addition reaction with a strong Bronsted acid such as hydrogen halide. Addition of two equivalents of hydrogen halide to a terminal alkyne produces a geminal dihalide, in which both the halide atoms are on the same carbon atom. The regioselectivity is in accordance with the Markovnikov’s rule. The hydrogen halide adds twice to generate the geminal dihalide. If hydrogen chloride is used as a reagent, the reaction goes through vinylic carbocation intermediate as the chlorine atom will stabilize the positive charge on the carbon atom through resonance. The alkyne must be symmetric to avoid producing a mixture of isomers.

Interpretation Introduction

(b)

Interpretation:

How to synthesize the given compound from an alkyne is to be described.

Concept introduction:

The carbon-carbon triple bond in terminal alkynes is electron rich and thus undergoes electrophilic addition reaction with a strong Bronsted acid such as hydrogen halide. Addition of two equivalents of hydrogen halide to a terminal alkyne produces a geminal dihalide, in which both the halide atoms are on the same carbon atom. The regioselectivity is in accordance with the Markovnikov’s rule. The hydrogen halide adds twice to generate the geminal dihalide. If hydrogen bromide is used as a reagent, the reaction goes through formation of a pi complex with an alkyne. This pi complex is stabilized by the attraction between electron rich triple bond and electron poor proton of the acid. The alkyne must be symmetric to avoid producing a mixture of isomers. An unsymmetric alkyne produces a mixture of isomers.

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Predict the major products of both organic reactions. Be sure to use wedge and dash bonds to show the stereochemistry of the products when it's important, for example to distinguish between two different major products. esc esc Explanation Check 2 : + + X H₁₂O + Х ง WW E R Y qab Ccaps lock shift $ P X Click and drag to start drawing a structure. © 2025 McGraw Hill LLC. All Rights Reserved. Terms of Use | Privacy Center | Accessibility Bil T FR F18 9 G t K L Z X V B N M control opption command command T C d

Draw the Markovnikov product of the hydrohalogenation of this alkene. this problem. Note for advanced students: draw only one product, and don't worry about showing any stereochemistry. Drawing dash and wedge bonds has been disabled for caps lock Explanation Check 2 W E R + X 5 HCI Click and drag to start drawing a structure. © 2025 McGraw Hill LLC. All Rights Reserved. Terms of Use | Privacy Center | Accessibility Bil Y F G H K L ZZ X C V B N M control opption command F10 F10 command 4 BA Ar C

I don't understand why the amide on the top left, with the R attached to one side, doesn't get substituted with OH to form a carboxylic acid. And if only one can be substituted, why did it choose the amide it chose rather than the other amide?

Answer 2

Question

Chapter 11, Problem 11.14P

Interpretation Introduction

(a)

Interpretation:

How to synthesize the given compound from an alkyne is to be described.

Concept introduction:

The carbon-carbon triple bond in terminal alkynes is electron rich and thus undergoes electrophilic addition reaction with a strong Bronsted acid such as hydrogen halide. Addition of two equivalents of hydrogen halide to a terminal alkyne produces a geminal dihalide, in which both the halide atoms are on the same carbon atom. The regioselectivity is in accordance with the Markovnikov’s rule. The hydrogen halide adds twice to generate the geminal dihalide. If hydrogen chloride is used as a reagent, the reaction goes through vinylic carbocation intermediate as the chlorine atom will stabilize the positive charge on the carbon atom through resonance. The alkyne must be symmetric to avoid producing a mixture of isomers.

Interpretation Introduction

(b)

Interpretation:

How to synthesize the given compound from an alkyne is to be described.

Concept introduction:

The carbon-carbon triple bond in terminal alkynes is electron rich and thus undergoes electrophilic addition reaction with a strong Bronsted acid such as hydrogen halide. Addition of two equivalents of hydrogen halide to a terminal alkyne produces a geminal dihalide, in which both the halide atoms are on the same carbon atom. The regioselectivity is in accordance with the Markovnikov’s rule. The hydrogen halide adds twice to generate the geminal dihalide. If hydrogen bromide is used as a reagent, the reaction goes through formation of a pi complex with an alkyne. This pi complex is stabilized by the attraction between electron rich triple bond and electron poor proton of the acid. The alkyne must be symmetric to avoid producing a mixture of isomers. An unsymmetric alkyne produces a mixture of isomers.

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Answer 3

Question

Chapter 11, Problem 11.14P

Interpretation Introduction

(a)

Interpretation:

How to synthesize the given compound from an alkyne is to be described.

Concept introduction:

The carbon-carbon triple bond in terminal alkynes is electron rich and thus undergoes electrophilic addition reaction with a strong Bronsted acid such as hydrogen halide. Addition of two equivalents of hydrogen halide to a terminal alkyne produces a geminal dihalide, in which both the halide atoms are on the same carbon atom. The regioselectivity is in accordance with the Markovnikov’s rule. The hydrogen halide adds twice to generate the geminal dihalide. If hydrogen chloride is used as a reagent, the reaction goes through vinylic carbocation intermediate as the chlorine atom will stabilize the positive charge on the carbon atom through resonance. The alkyne must be symmetric to avoid producing a mixture of isomers.

Interpretation Introduction

(b)

Interpretation:

How to synthesize the given compound from an alkyne is to be described.

Concept introduction:

The carbon-carbon triple bond in terminal alkynes is electron rich and thus undergoes electrophilic addition reaction with a strong Bronsted acid such as hydrogen halide. Addition of two equivalents of hydrogen halide to a terminal alkyne produces a geminal dihalide, in which both the halide atoms are on the same carbon atom. The regioselectivity is in accordance with the Markovnikov’s rule. The hydrogen halide adds twice to generate the geminal dihalide. If hydrogen bromide is used as a reagent, the reaction goes through formation of a pi complex with an alkyne. This pi complex is stabilized by the attraction between electron rich triple bond and electron poor proton of the acid. The alkyne must be symmetric to avoid producing a mixture of isomers. An unsymmetric alkyne produces a mixture of isomers.

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Answer 4

Question

Chapter 11, Problem 11.14P

Interpretation Introduction

(a)

Interpretation:

How to synthesize the given compound from an alkyne is to be described.

Concept introduction:

The carbon-carbon triple bond in terminal alkynes is electron rich and thus undergoes electrophilic addition reaction with a strong Bronsted acid such as hydrogen halide. Addition of two equivalents of hydrogen halide to a terminal alkyne produces a geminal dihalide, in which both the halide atoms are on the same carbon atom. The regioselectivity is in accordance with the Markovnikov’s rule. The hydrogen halide adds twice to generate the geminal dihalide. If hydrogen chloride is used as a reagent, the reaction goes through vinylic carbocation intermediate as the chlorine atom will stabilize the positive charge on the carbon atom through resonance. The alkyne must be symmetric to avoid producing a mixture of isomers.

Interpretation Introduction

(b)

Interpretation:

How to synthesize the given compound from an alkyne is to be described.

Concept introduction:

The carbon-carbon triple bond in terminal alkynes is electron rich and thus undergoes electrophilic addition reaction with a strong Bronsted acid such as hydrogen halide. Addition of two equivalents of hydrogen halide to a terminal alkyne produces a geminal dihalide, in which both the halide atoms are on the same carbon atom. The regioselectivity is in accordance with the Markovnikov’s rule. The hydrogen halide adds twice to generate the geminal dihalide. If hydrogen bromide is used as a reagent, the reaction goes through formation of a pi complex with an alkyne. This pi complex is stabilized by the attraction between electron rich triple bond and electron poor proton of the acid. The alkyne must be symmetric to avoid producing a mixture of isomers. An unsymmetric alkyne produces a mixture of isomers.

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Answer 5

Chapter 11, Problem 11.14P

Interpretation Introduction

(a)

Interpretation:

How to synthesize the given compound from an alkyne is to be described.

Concept introduction:

The carbon-carbon triple bond in terminal alkynes is electron rich and thus undergoes electrophilic addition reaction with a strong Bronsted acid such as hydrogen halide. Addition of two equivalents of hydrogen halide to a terminal alkyne produces a geminal dihalide, in which both the halide atoms are on the same carbon atom. The regioselectivity is in accordance with the Markovnikov’s rule. The hydrogen halide adds twice to generate the geminal dihalide. If hydrogen chloride is used as a reagent, the reaction goes through vinylic carbocation intermediate as the chlorine atom will stabilize the positive charge on the carbon atom through resonance. The alkyne must be symmetric to avoid producing a mixture of isomers.

Interpretation Introduction

(b)

Interpretation:

How to synthesize the given compound from an alkyne is to be described.

Concept introduction:

The carbon-carbon triple bond in terminal alkynes is electron rich and thus undergoes electrophilic addition reaction with a strong Bronsted acid such as hydrogen halide. Addition of two equivalents of hydrogen halide to a terminal alkyne produces a geminal dihalide, in which both the halide atoms are on the same carbon atom. The regioselectivity is in accordance with the Markovnikov’s rule. The hydrogen halide adds twice to generate the geminal dihalide. If hydrogen bromide is used as a reagent, the reaction goes through formation of a pi complex with an alkyne. This pi complex is stabilized by the attraction between electron rich triple bond and electron poor proton of the acid. The alkyne must be symmetric to avoid producing a mixture of isomers. An unsymmetric alkyne produces a mixture of isomers.

Answer 6

Chapter 11, Problem 11.14P

Interpretation Introduction

(a)

Interpretation:

How to synthesize the given compound from an alkyne is to be described.

Concept introduction:

The carbon-carbon triple bond in terminal alkynes is electron rich and thus undergoes electrophilic addition reaction with a strong Bronsted acid such as hydrogen halide. Addition of two equivalents of hydrogen halide to a terminal alkyne produces a geminal dihalide, in which both the halide atoms are on the same carbon atom. The regioselectivity is in accordance with the Markovnikov’s rule. The hydrogen halide adds twice to generate the geminal dihalide. If hydrogen chloride is used as a reagent, the reaction goes through vinylic carbocation intermediate as the chlorine atom will stabilize the positive charge on the carbon atom through resonance. The alkyne must be symmetric to avoid producing a mixture of isomers.

Answer 7

Chapter 11, Problem 11.14P

Interpretation Introduction

(a)

Interpretation:

How to synthesize the given compound from an alkyne is to be described.

Concept introduction:

The carbon-carbon triple bond in terminal alkynes is electron rich and thus undergoes electrophilic addition reaction with a strong Bronsted acid such as hydrogen halide. Addition of two equivalents of hydrogen halide to a terminal alkyne produces a geminal dihalide, in which both the halide atoms are on the same carbon atom. The regioselectivity is in accordance with the Markovnikov’s rule. The hydrogen halide adds twice to generate the geminal dihalide. If hydrogen chloride is used as a reagent, the reaction goes through vinylic carbocation intermediate as the chlorine atom will stabilize the positive charge on the carbon atom through resonance. The alkyne must be symmetric to avoid producing a mixture of isomers.

Answer 8

Interpretation Introduction

(b)

Interpretation:

How to synthesize the given compound from an alkyne is to be described.

Concept introduction:

The carbon-carbon triple bond in terminal alkynes is electron rich and thus undergoes electrophilic addition reaction with a strong Bronsted acid such as hydrogen halide. Addition of two equivalents of hydrogen halide to a terminal alkyne produces a geminal dihalide, in which both the halide atoms are on the same carbon atom. The regioselectivity is in accordance with the Markovnikov’s rule. The hydrogen halide adds twice to generate the geminal dihalide. If hydrogen bromide is used as a reagent, the reaction goes through formation of a pi complex with an alkyne. This pi complex is stabilized by the attraction between electron rich triple bond and electron poor proton of the acid. The alkyne must be symmetric to avoid producing a mixture of isomers. An unsymmetric alkyne produces a mixture of isomers.

Answer 9

Interpretation Introduction

(b)

Interpretation:

How to synthesize the given compound from an alkyne is to be described.

Concept introduction:

The carbon-carbon triple bond in terminal alkynes is electron rich and thus undergoes electrophilic addition reaction with a strong Bronsted acid such as hydrogen halide. Addition of two equivalents of hydrogen halide to a terminal alkyne produces a geminal dihalide, in which both the halide atoms are on the same carbon atom. The regioselectivity is in accordance with the Markovnikov’s rule. The hydrogen halide adds twice to generate the geminal dihalide. If hydrogen bromide is used as a reagent, the reaction goes through formation of a pi complex with an alkyne. This pi complex is stabilized by the attraction between electron rich triple bond and electron poor proton of the acid. The alkyne must be symmetric to avoid producing a mixture of isomers. An unsymmetric alkyne produces a mixture of isomers.

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 how to synthesize the given compound from an alkyne.

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