(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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In the acid-catalyzed aromatic alkylation involving 1-methylcyclohexene and benzene, two isomeric products are possible, but only one is formed, as shown here. Draw the complete mechanism that leads to each product, and explain why only one isomer is formed.

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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