(a) Interpretation: An explanation as to why the rate of iodination of optically active 1-phenyl-2-methyl-1-butanone in acetic acid/ HN O 3 and the rate of racemization of 1-phenyl-2-methyl-1-butanone are identical in the same conditions is to be stated. Concept Introduction: Halogenation reaction of ketone takes place at the α carbon. Halogenation reaction can takes place either in acidic or in basic medium. Racemic mixture is the mixture containing equal amount of two enantiomers. Racemization is the process of formation of a racemic mixture.

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Answer 1

Question

Chapter 22, Problem 22.13P

Interpretation Introduction

(a)

Interpretation:

An explanation as to why the rate of iodination of optically active 1-phenyl-2-methyl-1-butanone in acetic acid/HNO3 and the rate of racemization of 1-phenyl-2-methyl-1-butanone are identical in the same conditions is to be stated.

Concept Introduction:

Halogenation reaction of ketone takes place at the α carbon. Halogenation reaction can takes place either in acidic or in basic medium. Racemic mixture is the mixture containing equal amount of two enantiomers. Racemization is the process of formation of a racemic mixture.

Interpretation Introduction

(b)

Interpretation:

An explanation as to why the rate of bromination and iodination of acetophenone are identical at a given acid concentration is to be stated.

Concept Introduction:

Halogenation reaction of ketone takes place at the α carbon. Halogenation reaction can takes place either in acidic or in basic medium. In the halogenation reaction of ketone first keto gets converted into enol then halogen gets added to the enol structure to form intermediate which after elimination of HX forms haloketone.

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When ethyl bromide is added to potassium tert-butoxide, the product is ethyl tert-butyl ether.(a) What happens to the reaction rate if the concentration of ethyl bromide is doubled?

When ethyl bromide is added to potassium tert-butoxide, the product is ethyl tert-butyl ether. (a) What happens to the rate if the concentration of potassium tert-butoxide is tripled and the concentration of ethyl bromide is doubled?

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Answer 2

Question

Chapter 22, Problem 22.13P

Interpretation Introduction

(a)

Interpretation:

An explanation as to why the rate of iodination of optically active 1-phenyl-2-methyl-1-butanone in acetic acid/HNO3 and the rate of racemization of 1-phenyl-2-methyl-1-butanone are identical in the same conditions is to be stated.

Concept Introduction:

Halogenation reaction of ketone takes place at the α carbon. Halogenation reaction can takes place either in acidic or in basic medium. Racemic mixture is the mixture containing equal amount of two enantiomers. Racemization is the process of formation of a racemic mixture.

Interpretation Introduction

(b)

Interpretation:

An explanation as to why the rate of bromination and iodination of acetophenone are identical at a given acid concentration is to be stated.

Concept Introduction:

Halogenation reaction of ketone takes place at the α carbon. Halogenation reaction can takes place either in acidic or in basic medium. In the halogenation reaction of ketone first keto gets converted into enol then halogen gets added to the enol structure to form intermediate which after elimination of HX forms haloketone.

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Answer 3

Question

Chapter 22, Problem 22.13P

Interpretation Introduction

(a)

Interpretation:

An explanation as to why the rate of iodination of optically active 1-phenyl-2-methyl-1-butanone in acetic acid/HNO3 and the rate of racemization of 1-phenyl-2-methyl-1-butanone are identical in the same conditions is to be stated.

Concept Introduction:

Halogenation reaction of ketone takes place at the α carbon. Halogenation reaction can takes place either in acidic or in basic medium. Racemic mixture is the mixture containing equal amount of two enantiomers. Racemization is the process of formation of a racemic mixture.

Interpretation Introduction

(b)

Interpretation:

An explanation as to why the rate of bromination and iodination of acetophenone are identical at a given acid concentration is to be stated.

Concept Introduction:

Halogenation reaction of ketone takes place at the α carbon. Halogenation reaction can takes place either in acidic or in basic medium. In the halogenation reaction of ketone first keto gets converted into enol then halogen gets added to the enol structure to form intermediate which after elimination of HX forms haloketone.

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Answer 4

Question

Chapter 22, Problem 22.13P

Interpretation Introduction

(a)

Interpretation:

An explanation as to why the rate of iodination of optically active 1-phenyl-2-methyl-1-butanone in acetic acid/HNO3 and the rate of racemization of 1-phenyl-2-methyl-1-butanone are identical in the same conditions is to be stated.

Concept Introduction:

Halogenation reaction of ketone takes place at the α carbon. Halogenation reaction can takes place either in acidic or in basic medium. Racemic mixture is the mixture containing equal amount of two enantiomers. Racemization is the process of formation of a racemic mixture.

Interpretation Introduction

(b)

Interpretation:

An explanation as to why the rate of bromination and iodination of acetophenone are identical at a given acid concentration is to be stated.

Concept Introduction:

Halogenation reaction of ketone takes place at the α carbon. Halogenation reaction can takes place either in acidic or in basic medium. In the halogenation reaction of ketone first keto gets converted into enol then halogen gets added to the enol structure to form intermediate which after elimination of HX forms haloketone.

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Answer 5

Chapter 22, Problem 22.13P

Interpretation Introduction

(a)

Interpretation:

An explanation as to why the rate of iodination of optically active 1-phenyl-2-methyl-1-butanone in acetic acid/HNO3 and the rate of racemization of 1-phenyl-2-methyl-1-butanone are identical in the same conditions is to be stated.

Concept Introduction:

Halogenation reaction of ketone takes place at the α carbon. Halogenation reaction can takes place either in acidic or in basic medium. Racemic mixture is the mixture containing equal amount of two enantiomers. Racemization is the process of formation of a racemic mixture.

Interpretation Introduction

(b)

Interpretation:

An explanation as to why the rate of bromination and iodination of acetophenone are identical at a given acid concentration is to be stated.

Concept Introduction:

Halogenation reaction of ketone takes place at the α carbon. Halogenation reaction can takes place either in acidic or in basic medium. In the halogenation reaction of ketone first keto gets converted into enol then halogen gets added to the enol structure to form intermediate which after elimination of HX forms haloketone.

Answer 6

Chapter 22, Problem 22.13P

Interpretation Introduction

(a)

Interpretation:

An explanation as to why the rate of iodination of optically active 1-phenyl-2-methyl-1-butanone in acetic acid/HNO3 and the rate of racemization of 1-phenyl-2-methyl-1-butanone are identical in the same conditions is to be stated.

Concept Introduction:

Halogenation reaction of ketone takes place at the α carbon. Halogenation reaction can takes place either in acidic or in basic medium. Racemic mixture is the mixture containing equal amount of two enantiomers. Racemization is the process of formation of a racemic mixture.

Answer 7

Chapter 22, Problem 22.13P

Interpretation Introduction

(a)

Interpretation:

An explanation as to why the rate of iodination of optically active 1-phenyl-2-methyl-1-butanone in acetic acid/HNO3 and the rate of racemization of 1-phenyl-2-methyl-1-butanone are identical in the same conditions is to be stated.

Concept Introduction:

Halogenation reaction of ketone takes place at the α carbon. Halogenation reaction can takes place either in acidic or in basic medium. Racemic mixture is the mixture containing equal amount of two enantiomers. Racemization is the process of formation of a racemic mixture.

Answer 8

Interpretation Introduction

(b)

Interpretation:

An explanation as to why the rate of bromination and iodination of acetophenone are identical at a given acid concentration is to be stated.

Concept Introduction:

Halogenation reaction of ketone takes place at the α carbon. Halogenation reaction can takes place either in acidic or in basic medium. In the halogenation reaction of ketone first keto gets converted into enol then halogen gets added to the enol structure to form intermediate which after elimination of HX forms haloketone.

Answer 9

Interpretation Introduction

(b)

Interpretation:

An explanation as to why the rate of bromination and iodination of acetophenone are identical at a given acid concentration is to be stated.

Concept Introduction:

Halogenation reaction of ketone takes place at the α carbon. Halogenation reaction can takes place either in acidic or in basic medium. In the halogenation reaction of ketone first keto gets converted into enol then halogen gets added to the enol structure to form intermediate which after elimination of HX forms haloketone.

Answer 10

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Answer 11

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Answer 12

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Answer 13

Ch. 22 - Prob. 22.1P Ch. 22 - Prob. 22.2P Ch. 22 - Prob. 22.3P Ch. 22 - Prob. 22.4P Ch. 22 - Prob. 22.5P Ch. 22 - Prob. 22.6P Ch. 22 - Prob. 22.7P Ch. 22 - Prob. 22.8P Ch. 22 - Prob. 22.9P Ch. 22 - Prob. 22.10P

Solution Summary: The author explains that the rate of iodination of optically active 1-phenyl-2-methyl-1-butanone in aqueous acetic acid is identical.

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Chapter 22 Solutions