To explain the mechanism of ketone undergoes acid-catalyzed chlorination, acid-catalyzed bromination, racemization and acid-catalyzed deuterium exchange at the alpha carbon have similar rate constants. Concept introduction: When a ketone or aldehyde reacts with an acid, it protonates the carbonyl oxygen to form an enolate ion. The amount of carbonyl compound converted into an enolate ion depend on the p K a of the carbonyl compound. The tautomers are the isomers that are in rapid equilibrium. A ketone exists in equilibrium with its enol tautomer. For most ketones , the keto tautomer is much stable than the enol tautomer.

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Answer 1

Question

Chapter 17.4, Problem 10P

Interpretation Introduction

Interpretation: To explain the mechanism of ketone undergoes acid-catalyzed chlorination, acid-catalyzed bromination, racemization and acid-catalyzed deuterium exchange at the alpha carbon have similar rate constants.

Concept introduction: When a ketone or aldehyde reacts with an acid, it protonates the carbonyl oxygen to form an enolate ion. The amount of carbonyl compound converted into an enolate ion depend on the pKa of the carbonyl compound.

The tautomers are the isomers that are in rapid equilibrium. A ketone exists in equilibrium with its enol tautomer.

For most ketones, the keto tautomer is much stable than the enol tautomer.

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Answer 2

Question

Chapter 17.4, Problem 10P

Interpretation Introduction

Interpretation: To explain the mechanism of ketone undergoes acid-catalyzed chlorination, acid-catalyzed bromination, racemization and acid-catalyzed deuterium exchange at the alpha carbon have similar rate constants.

Concept introduction: When a ketone or aldehyde reacts with an acid, it protonates the carbonyl oxygen to form an enolate ion. The amount of carbonyl compound converted into an enolate ion depend on the pKa of the carbonyl compound.

The tautomers are the isomers that are in rapid equilibrium. A ketone exists in equilibrium with its enol tautomer.

For most ketones, the keto tautomer is much stable than the enol tautomer.

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Answer 3

Question

Chapter 17.4, Problem 10P

Interpretation Introduction

Interpretation: To explain the mechanism of ketone undergoes acid-catalyzed chlorination, acid-catalyzed bromination, racemization and acid-catalyzed deuterium exchange at the alpha carbon have similar rate constants.

Concept introduction: When a ketone or aldehyde reacts with an acid, it protonates the carbonyl oxygen to form an enolate ion. The amount of carbonyl compound converted into an enolate ion depend on the pKa of the carbonyl compound.

The tautomers are the isomers that are in rapid equilibrium. A ketone exists in equilibrium with its enol tautomer.

For most ketones, the keto tautomer is much stable than the enol tautomer.

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Answer 4

Question

Chapter 17.4, Problem 10P

Interpretation Introduction

Interpretation: To explain the mechanism of ketone undergoes acid-catalyzed chlorination, acid-catalyzed bromination, racemization and acid-catalyzed deuterium exchange at the alpha carbon have similar rate constants.

Concept introduction: When a ketone or aldehyde reacts with an acid, it protonates the carbonyl oxygen to form an enolate ion. The amount of carbonyl compound converted into an enolate ion depend on the pKa of the carbonyl compound.

The tautomers are the isomers that are in rapid equilibrium. A ketone exists in equilibrium with its enol tautomer.

For most ketones, the keto tautomer is much stable than the enol tautomer.

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Answer 5

Chapter 17.4, Problem 10P

Interpretation Introduction

Interpretation: To explain the mechanism of ketone undergoes acid-catalyzed chlorination, acid-catalyzed bromination, racemization and acid-catalyzed deuterium exchange at the alpha carbon have similar rate constants.

Concept introduction: When a ketone or aldehyde reacts with an acid, it protonates the carbonyl oxygen to form an enolate ion. The amount of carbonyl compound converted into an enolate ion depend on the pKa of the carbonyl compound.

The tautomers are the isomers that are in rapid equilibrium. A ketone exists in equilibrium with its enol tautomer.

For most ketones, the keto tautomer is much stable than the enol tautomer.

Answer 6

Chapter 17.4, Problem 10P

Interpretation Introduction

Interpretation: To explain the mechanism of ketone undergoes acid-catalyzed chlorination, acid-catalyzed bromination, racemization and acid-catalyzed deuterium exchange at the alpha carbon have similar rate constants.

Concept introduction: When a ketone or aldehyde reacts with an acid, it protonates the carbonyl oxygen to form an enolate ion. The amount of carbonyl compound converted into an enolate ion depend on the pKa of the carbonyl compound.

The tautomers are the isomers that are in rapid equilibrium. A ketone exists in equilibrium with its enol tautomer.

For most ketones, the keto tautomer is much stable than the enol tautomer.

Answer 7

Chapter 17.4, Problem 10P

Interpretation Introduction

Interpretation: To explain the mechanism of ketone undergoes acid-catalyzed chlorination, acid-catalyzed bromination, racemization and acid-catalyzed deuterium exchange at the alpha carbon have similar rate constants.

Concept introduction: When a ketone or aldehyde reacts with an acid, it protonates the carbonyl oxygen to form an enolate ion. The amount of carbonyl compound converted into an enolate ion depend on the pKa of the carbonyl compound.

The tautomers are the isomers that are in rapid equilibrium. A ketone exists in equilibrium with its enol tautomer.

For most ketones, the keto tautomer is much stable than the enol tautomer.

Answer 8

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Answer 9

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Answer 10

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Answer 11

Ch. 17.1 - Prob. 1P Ch. 17.1 - Prob. 2P Ch. 17.1 - Prob. 3P Ch. 17.1 - Prob. 4P Ch. 17.1 - Rank the compounds in each of the following groups...Ch. 17.2 - Explain why 92% of 2,4-pemtanedione exists as the...Ch. 17.3 - Draw the enol tautomers for each of the following...Ch. 17.3 - Prob. 8P Ch. 17.4 - Prob. 9P Ch. 17.4 - Prob. 10P

Solution Summary: The author explains the mechanism of ketone undergoes acid-catalyzed chlorination and electrophilic bromination. The amount of carbonyl compound converted into an enolate ion depends on

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Chapter 17 Solutions