(a) Interpretation: The reaction and complete, detailed mechanism for the reaction is to be drawn. Concept introduction: Acid-catalyzed hydration of an alkyne produces a ketone . Step 1 is the electrophilic addition of H + , which gives a resonance-stabilized vinylic carbocation intermediate. In step 2, water behaves as a nucleophile, attacking the positively charged C of that intermediate. Deprotonation in Step 3 produces the uncharged OH group, which is attached to the alkene C. The product of it is an enol. Under acidic conditions, the enol rapidly tautomerizes to the more stable keto form.

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Answer 1

Question

Chapter 11, Problem 11.40P

Interpretation Introduction

(a)

Interpretation:

The reaction and complete, detailed mechanism for the reaction is to be drawn.

Concept introduction:

Acid-catalyzed hydration of an alkyne produces a ketone. Step 1 is the electrophilic addition of H+, which gives a resonance-stabilized vinylic carbocation intermediate. In step 2, water behaves as a nucleophile, attacking the positively charged C of that intermediate. Deprotonation in Step 3 produces the uncharged OH group, which is attached to the alkene C. The product of it is an enol. Under acidic conditions, the enol rapidly tautomerizes to the more stable keto form.

Interpretation Introduction

(b)

Interpretation:

The reaction and complete, detailed mechanism for the reaction is to be drawn.

Concept introduction:

Acid-catalyzed hydration of an alkyne produces a ketone. Step 1 is the electrophilic addition of H+, which gives a resonance-stabilized vinylic carbocation intermediate. In step 2, water behaves as a nucleophile, attacking the positively charged C of that intermediate. Deprotonation in Step 3 produces the uncharged OH group, which is attached to the alkene C. The product of it is an enol. Under acidic conditions, the enol rapidly tautomerizes to the more stable keto form.

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(SYN) Show how each of the following compounds can be synthesized from an acid chloride and either water, an alcohol, or an amine. For each reaction, provide the complete, detailed mechanism.

Draw the complete, detailed mechanism for each of the following reactions and predict the major products.

Draw the complete, detailed mechanism and the products for each of the following reactions.

Answer 2

Question

Chapter 11, Problem 11.40P

Interpretation Introduction

(a)

Interpretation:

The reaction and complete, detailed mechanism for the reaction is to be drawn.

Concept introduction:

Acid-catalyzed hydration of an alkyne produces a ketone. Step 1 is the electrophilic addition of H+, which gives a resonance-stabilized vinylic carbocation intermediate. In step 2, water behaves as a nucleophile, attacking the positively charged C of that intermediate. Deprotonation in Step 3 produces the uncharged OH group, which is attached to the alkene C. The product of it is an enol. Under acidic conditions, the enol rapidly tautomerizes to the more stable keto form.

Interpretation Introduction

(b)

Interpretation:

The reaction and complete, detailed mechanism for the reaction is to be drawn.

Concept introduction:

Acid-catalyzed hydration of an alkyne produces a ketone. Step 1 is the electrophilic addition of H+, which gives a resonance-stabilized vinylic carbocation intermediate. In step 2, water behaves as a nucleophile, attacking the positively charged C of that intermediate. Deprotonation in Step 3 produces the uncharged OH group, which is attached to the alkene C. The product of it is an enol. Under acidic conditions, the enol rapidly tautomerizes to the more stable keto form.

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Answer 3

Question

Chapter 11, Problem 11.40P

Interpretation Introduction

(a)

Interpretation:

The reaction and complete, detailed mechanism for the reaction is to be drawn.

Concept introduction:

Acid-catalyzed hydration of an alkyne produces a ketone. Step 1 is the electrophilic addition of H+, which gives a resonance-stabilized vinylic carbocation intermediate. In step 2, water behaves as a nucleophile, attacking the positively charged C of that intermediate. Deprotonation in Step 3 produces the uncharged OH group, which is attached to the alkene C. The product of it is an enol. Under acidic conditions, the enol rapidly tautomerizes to the more stable keto form.

Interpretation Introduction

(b)

Interpretation:

The reaction and complete, detailed mechanism for the reaction is to be drawn.

Concept introduction:

Acid-catalyzed hydration of an alkyne produces a ketone. Step 1 is the electrophilic addition of H+, which gives a resonance-stabilized vinylic carbocation intermediate. In step 2, water behaves as a nucleophile, attacking the positively charged C of that intermediate. Deprotonation in Step 3 produces the uncharged OH group, which is attached to the alkene C. The product of it is an enol. Under acidic conditions, the enol rapidly tautomerizes to the more stable keto form.

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Answer 4

Question

Chapter 11, Problem 11.40P

Interpretation Introduction

(a)

Interpretation:

The reaction and complete, detailed mechanism for the reaction is to be drawn.

Concept introduction:

Acid-catalyzed hydration of an alkyne produces a ketone. Step 1 is the electrophilic addition of H+, which gives a resonance-stabilized vinylic carbocation intermediate. In step 2, water behaves as a nucleophile, attacking the positively charged C of that intermediate. Deprotonation in Step 3 produces the uncharged OH group, which is attached to the alkene C. The product of it is an enol. Under acidic conditions, the enol rapidly tautomerizes to the more stable keto form.

Interpretation Introduction

(b)

Interpretation:

The reaction and complete, detailed mechanism for the reaction is to be drawn.

Concept introduction:

Acid-catalyzed hydration of an alkyne produces a ketone. Step 1 is the electrophilic addition of H+, which gives a resonance-stabilized vinylic carbocation intermediate. In step 2, water behaves as a nucleophile, attacking the positively charged C of that intermediate. Deprotonation in Step 3 produces the uncharged OH group, which is attached to the alkene C. The product of it is an enol. Under acidic conditions, the enol rapidly tautomerizes to the more stable keto form.

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Answer 5

Chapter 11, Problem 11.40P

Interpretation Introduction

(a)

Interpretation:

The reaction and complete, detailed mechanism for the reaction is to be drawn.

Concept introduction:

Acid-catalyzed hydration of an alkyne produces a ketone. Step 1 is the electrophilic addition of H+, which gives a resonance-stabilized vinylic carbocation intermediate. In step 2, water behaves as a nucleophile, attacking the positively charged C of that intermediate. Deprotonation in Step 3 produces the uncharged OH group, which is attached to the alkene C. The product of it is an enol. Under acidic conditions, the enol rapidly tautomerizes to the more stable keto form.

Interpretation Introduction

(b)

Interpretation:

The reaction and complete, detailed mechanism for the reaction is to be drawn.

Concept introduction:

Acid-catalyzed hydration of an alkyne produces a ketone. Step 1 is the electrophilic addition of H+, which gives a resonance-stabilized vinylic carbocation intermediate. In step 2, water behaves as a nucleophile, attacking the positively charged C of that intermediate. Deprotonation in Step 3 produces the uncharged OH group, which is attached to the alkene C. The product of it is an enol. Under acidic conditions, the enol rapidly tautomerizes to the more stable keto form.

Answer 6

Chapter 11, Problem 11.40P

Interpretation Introduction

(a)

Interpretation:

The reaction and complete, detailed mechanism for the reaction is to be drawn.

Concept introduction:

Acid-catalyzed hydration of an alkyne produces a ketone. Step 1 is the electrophilic addition of H+, which gives a resonance-stabilized vinylic carbocation intermediate. In step 2, water behaves as a nucleophile, attacking the positively charged C of that intermediate. Deprotonation in Step 3 produces the uncharged OH group, which is attached to the alkene C. The product of it is an enol. Under acidic conditions, the enol rapidly tautomerizes to the more stable keto form.

Answer 7

Chapter 11, Problem 11.40P

Interpretation Introduction

(a)

Interpretation:

The reaction and complete, detailed mechanism for the reaction is to be drawn.

Concept introduction:

Acid-catalyzed hydration of an alkyne produces a ketone. Step 1 is the electrophilic addition of H+, which gives a resonance-stabilized vinylic carbocation intermediate. In step 2, water behaves as a nucleophile, attacking the positively charged C of that intermediate. Deprotonation in Step 3 produces the uncharged OH group, which is attached to the alkene C. The product of it is an enol. Under acidic conditions, the enol rapidly tautomerizes to the more stable keto form.

Answer 8

Interpretation Introduction

(b)

Interpretation:

The reaction and complete, detailed mechanism for the reaction is to be drawn.

Concept introduction:

Acid-catalyzed hydration of an alkyne produces a ketone. Step 1 is the electrophilic addition of H+, which gives a resonance-stabilized vinylic carbocation intermediate. In step 2, water behaves as a nucleophile, attacking the positively charged C of that intermediate. Deprotonation in Step 3 produces the uncharged OH group, which is attached to the alkene C. The product of it is an enol. Under acidic conditions, the enol rapidly tautomerizes to the more stable keto form.

Answer 9

Interpretation Introduction

(b)

Interpretation:

The reaction and complete, detailed mechanism for the reaction is to be drawn.

Concept introduction:

Acid-catalyzed hydration of an alkyne produces a ketone. Step 1 is the electrophilic addition of H+, which gives a resonance-stabilized vinylic carbocation intermediate. In step 2, water behaves as a nucleophile, attacking the positively charged C of that intermediate. Deprotonation in Step 3 produces the uncharged OH group, which is attached to the alkene C. The product of it is an enol. Under acidic conditions, the enol rapidly tautomerizes to the more stable keto form.

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

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Chapter 11 Solutions