(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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Experiment: Each team will be provided with 5g of a mixture of acetanilide and salicylic acid. You will divide it into three 1.5 g portions in separate 125 mL Erlenmeyer flasks savıng some for melting point analysis. Dissolve the mixture in each flask in ~60mL of DI water by heating to boiling on a hotplate. Take the flasks off the hotplate once you have a clear solution and let them stand on the bench top for 5 mins and then allow them to cool as described below. Sample A-Let the first sample cool slowly to room temperature by letting it stand on your lab bench, with occasional stirring to promote crystallization. Sample B-Cool the second sample 1n a tap-water bath to 10-15 °C Sample C-Cool the third sample in an ice-bath to 0-2 °C Results: weight after recrystalization and melting point temp. A=0.624g,102-115° B=0.765g, 80-105° C=1.135g, 77-108 What is the percent yield of A,B, and C.

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 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