(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

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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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Draw a mechanism for the following synthetic transformation including reagents and any isolable intermediates throughout the process. Please clearly indicate bond cleavage/formation using curly arrows. MeO2C

CHEM 310 Quiz 8 Organic Chemistry II Due: Tuesday, April 25th, at 11:59 pm. This quiz is open textbook / open notes - but you must work alone. You cannot use the internet or the solutions manual for the book. Scan in your work and record an explanation of your mechanism. You may record this any way that you like. One way would be to start an individual Zoom meeting, start recording, "share your screen" and then talk through the problem. This will be converted to an .mp4 file that you can upload into Canvas using the "record/upload media" feature. Pyridine, benzoic acid and benzene are dissolved in ethyl acetate. Design and provide a plan / flow chart for separating and isolating each of these components. Pyridine and benzene are liquids at room temperature. Benzoic acid is a solid. You have ethyl acetate, 2M NaOH, 2M HCI and anhydrous MgSO4 available, as well as all the glassware and equipment that you used in the organic lab this year. Provide accurate acid/base reactions for any…

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 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