a) Interpretation: The enol tautomer of Cyclopentanone shown is to be given. Concept introduction: A carbonyl compound with a hydrogen atom on its α carbon atom is in equilibrium with its corresponding enol isomer. The spontaneous inter-conversion between two isomers usually with the change in position of a hydrogen is called tautomerism. The individual keto and enol isomers are called tautomers. To give: The enol tautomer of cyclopentanone shown.

Question

Ibufenac, a para-disubstituted arene with the structureHO2CCH2C6H4CH2CH(CH3)2 , is a much more potent analgesic thanaspirin, but it was never sold commercially because it caused livertoxicity in some clinical trials. Devise a synthesis of ibufenac frombenzene and organic halides having fewer than five carbons.

Answer 1

Question

Chapter 22.1, Problem 1P

Interpretation Introduction

a)

Interpretation:

The enol tautomer of Cyclopentanone shown is to be given.

Concept introduction:

A carbonyl compound with a hydrogen atom on its α carbon atom is in equilibrium with its corresponding enol isomer. The spontaneous inter-conversion between two isomers usually with the change in position of a hydrogen is called tautomerism. The individual keto and enol isomers are called tautomers.

To give:

The enol tautomer of cyclopentanone shown.

Interpretation Introduction

b)

Interpretation:

The enol tautomer of Methyl thioacetate shown is to be given.

Concept introduction:

A carbonyl compound with a hydrogen atom on its α carbon atom is in equilibrium with its corresponding enol isomer. The spontaneous inter-conversion between two isomers usually with the change in position of a hydrogen is called tautomerism. The individual keto and enol isomers are called tautomers.

To give:

The enol tautomer of Methyl thioacetate shown.

Interpretation Introduction

c)

Interpretation:

The enol tautomer of Ethyl acetate shown is to be given.

Concept introduction:

A carbonyl compound with a hydrogen atom on its α carbon atom is in equilibrium with its corresponding enol isomer. The spontaneous inter-conversion between two isomers usually with the change in position of a hydrogen is called tautomerism. The individual keto and enol isomers are called tautomers.

To give:

The enol tautomer of Ethyl acetate shown.

Interpretation Introduction

d)

Interpretation:

The enol tautomer of Propanal shown is to be given.

Concept introduction:

A carbonyl compound with a hydrogen atom on its α carbon atom is in equilibrium with its corresponding enol isomer. The spontaneous inter-conversion between two isomers usually with the change in position of a hydrogen is called tautomerism. The individual keto and enol isomers are called tautomers.

To give:

The enol tautomer of Propanal shown.

Interpretation Introduction

e)

Interpretation:

The enol tautomer of Acetic acid shown is to be given.

Concept introduction:

A carbonyl compound with a hydrogen atom on its α carbon atom is in equilibrium with its corresponding enol isomer. The spontaneous inter-conversion between two isomers usually with the change in position of a hydrogen is called tautomerism. The individual keto and enol isomers are called tautomers.

To give:

The enol tautomer of Acetic acid shown.

Interpretation Introduction

f)

Interpretation:

The enol tautomer of Phenylacetone shown is to be given.

Concept introduction:

A carbonyl compound with a hydrogen atom on its α carbon atom is in equilibrium with its corresponding enol isomer. The spontaneous inter-conversion between two isomers usually with the change in position of a hydrogen is called tautomerism. The individual keto and enol isomers are called tautomers.

To give:

The enol tautomer of Phenylaceton shown.

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Ibufenac, a para-disubstituted arene with the structureHO2CCH2C6H4CH2CH(CH3)2 , is a much more potent analgesic thanaspirin, but it was never sold commercially because it caused livertoxicity in some clinical trials. Devise a synthesis of ibufenac frombenzene and organic halides having fewer than five carbons.

Enalapril, a drug used to treat hypertension, is prepared from compounds D and E by reductive amination. What is the structure of enalapril?

Treatment of compound A (C8H17Br) with NaOCH2CH3 affords two constitutional isomers B and C. Ozonolysis of B affords CH2=O and (CH3CH2CH2)2C=O. Ozonolysis of C affords CH3CH2CH2COCH3 and CH3CH2CHO. What is the structure of A?

Answer 2

Question

Chapter 22.1, Problem 1P

Interpretation Introduction

a)

Interpretation:

The enol tautomer of Cyclopentanone shown is to be given.

Concept introduction:

A carbonyl compound with a hydrogen atom on its α carbon atom is in equilibrium with its corresponding enol isomer. The spontaneous inter-conversion between two isomers usually with the change in position of a hydrogen is called tautomerism. The individual keto and enol isomers are called tautomers.

To give:

The enol tautomer of cyclopentanone shown.

Interpretation Introduction

b)

Interpretation:

The enol tautomer of Methyl thioacetate shown is to be given.

Concept introduction:

A carbonyl compound with a hydrogen atom on its α carbon atom is in equilibrium with its corresponding enol isomer. The spontaneous inter-conversion between two isomers usually with the change in position of a hydrogen is called tautomerism. The individual keto and enol isomers are called tautomers.

To give:

The enol tautomer of Methyl thioacetate shown.

Interpretation Introduction

c)

Interpretation:

The enol tautomer of Ethyl acetate shown is to be given.

Concept introduction:

A carbonyl compound with a hydrogen atom on its α carbon atom is in equilibrium with its corresponding enol isomer. The spontaneous inter-conversion between two isomers usually with the change in position of a hydrogen is called tautomerism. The individual keto and enol isomers are called tautomers.

To give:

The enol tautomer of Ethyl acetate shown.

Interpretation Introduction

d)

Interpretation:

The enol tautomer of Propanal shown is to be given.

Concept introduction:

A carbonyl compound with a hydrogen atom on its α carbon atom is in equilibrium with its corresponding enol isomer. The spontaneous inter-conversion between two isomers usually with the change in position of a hydrogen is called tautomerism. The individual keto and enol isomers are called tautomers.

To give:

The enol tautomer of Propanal shown.

Interpretation Introduction

e)

Interpretation:

The enol tautomer of Acetic acid shown is to be given.

Concept introduction:

A carbonyl compound with a hydrogen atom on its α carbon atom is in equilibrium with its corresponding enol isomer. The spontaneous inter-conversion between two isomers usually with the change in position of a hydrogen is called tautomerism. The individual keto and enol isomers are called tautomers.

To give:

The enol tautomer of Acetic acid shown.

Interpretation Introduction

f)

Interpretation:

The enol tautomer of Phenylacetone shown is to be given.

Concept introduction:

A carbonyl compound with a hydrogen atom on its α carbon atom is in equilibrium with its corresponding enol isomer. The spontaneous inter-conversion between two isomers usually with the change in position of a hydrogen is called tautomerism. The individual keto and enol isomers are called tautomers.

To give:

The enol tautomer of Phenylaceton shown.

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Answer 3

Question

Chapter 22.1, Problem 1P

Interpretation Introduction

a)

Interpretation:

The enol tautomer of Cyclopentanone shown is to be given.

Concept introduction:

A carbonyl compound with a hydrogen atom on its α carbon atom is in equilibrium with its corresponding enol isomer. The spontaneous inter-conversion between two isomers usually with the change in position of a hydrogen is called tautomerism. The individual keto and enol isomers are called tautomers.

To give:

The enol tautomer of cyclopentanone shown.

Interpretation Introduction

b)

Interpretation:

The enol tautomer of Methyl thioacetate shown is to be given.

Concept introduction:

A carbonyl compound with a hydrogen atom on its α carbon atom is in equilibrium with its corresponding enol isomer. The spontaneous inter-conversion between two isomers usually with the change in position of a hydrogen is called tautomerism. The individual keto and enol isomers are called tautomers.

To give:

The enol tautomer of Methyl thioacetate shown.

Interpretation Introduction

c)

Interpretation:

The enol tautomer of Ethyl acetate shown is to be given.

Concept introduction:

A carbonyl compound with a hydrogen atom on its α carbon atom is in equilibrium with its corresponding enol isomer. The spontaneous inter-conversion between two isomers usually with the change in position of a hydrogen is called tautomerism. The individual keto and enol isomers are called tautomers.

To give:

The enol tautomer of Ethyl acetate shown.

Interpretation Introduction

d)

Interpretation:

The enol tautomer of Propanal shown is to be given.

Concept introduction:

A carbonyl compound with a hydrogen atom on its α carbon atom is in equilibrium with its corresponding enol isomer. The spontaneous inter-conversion between two isomers usually with the change in position of a hydrogen is called tautomerism. The individual keto and enol isomers are called tautomers.

To give:

The enol tautomer of Propanal shown.

Interpretation Introduction

e)

Interpretation:

The enol tautomer of Acetic acid shown is to be given.

Concept introduction:

A carbonyl compound with a hydrogen atom on its α carbon atom is in equilibrium with its corresponding enol isomer. The spontaneous inter-conversion between two isomers usually with the change in position of a hydrogen is called tautomerism. The individual keto and enol isomers are called tautomers.

To give:

The enol tautomer of Acetic acid shown.

Interpretation Introduction

f)

Interpretation:

The enol tautomer of Phenylacetone shown is to be given.

Concept introduction:

A carbonyl compound with a hydrogen atom on its α carbon atom is in equilibrium with its corresponding enol isomer. The spontaneous inter-conversion between two isomers usually with the change in position of a hydrogen is called tautomerism. The individual keto and enol isomers are called tautomers.

To give:

The enol tautomer of Phenylaceton shown.

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Answer 4

Question

Chapter 22.1, Problem 1P

Interpretation Introduction

a)

Interpretation:

The enol tautomer of Cyclopentanone shown is to be given.

Concept introduction:

A carbonyl compound with a hydrogen atom on its α carbon atom is in equilibrium with its corresponding enol isomer. The spontaneous inter-conversion between two isomers usually with the change in position of a hydrogen is called tautomerism. The individual keto and enol isomers are called tautomers.

To give:

The enol tautomer of cyclopentanone shown.

Interpretation Introduction

b)

Interpretation:

The enol tautomer of Methyl thioacetate shown is to be given.

Concept introduction:

A carbonyl compound with a hydrogen atom on its α carbon atom is in equilibrium with its corresponding enol isomer. The spontaneous inter-conversion between two isomers usually with the change in position of a hydrogen is called tautomerism. The individual keto and enol isomers are called tautomers.

To give:

The enol tautomer of Methyl thioacetate shown.

Interpretation Introduction

c)

Interpretation:

The enol tautomer of Ethyl acetate shown is to be given.

Concept introduction:

A carbonyl compound with a hydrogen atom on its α carbon atom is in equilibrium with its corresponding enol isomer. The spontaneous inter-conversion between two isomers usually with the change in position of a hydrogen is called tautomerism. The individual keto and enol isomers are called tautomers.

To give:

The enol tautomer of Ethyl acetate shown.

Interpretation Introduction

d)

Interpretation:

The enol tautomer of Propanal shown is to be given.

Concept introduction:

A carbonyl compound with a hydrogen atom on its α carbon atom is in equilibrium with its corresponding enol isomer. The spontaneous inter-conversion between two isomers usually with the change in position of a hydrogen is called tautomerism. The individual keto and enol isomers are called tautomers.

To give:

The enol tautomer of Propanal shown.

Interpretation Introduction

e)

Interpretation:

The enol tautomer of Acetic acid shown is to be given.

Concept introduction:

A carbonyl compound with a hydrogen atom on its α carbon atom is in equilibrium with its corresponding enol isomer. The spontaneous inter-conversion between two isomers usually with the change in position of a hydrogen is called tautomerism. The individual keto and enol isomers are called tautomers.

To give:

The enol tautomer of Acetic acid shown.

Interpretation Introduction

f)

Interpretation:

The enol tautomer of Phenylacetone shown is to be given.

Concept introduction:

A carbonyl compound with a hydrogen atom on its α carbon atom is in equilibrium with its corresponding enol isomer. The spontaneous inter-conversion between two isomers usually with the change in position of a hydrogen is called tautomerism. The individual keto and enol isomers are called tautomers.

To give:

The enol tautomer of Phenylaceton shown.

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Answer 5

Chapter 22.1, Problem 1P

Interpretation Introduction

a)

Interpretation:

The enol tautomer of Cyclopentanone shown is to be given.

Concept introduction:

A carbonyl compound with a hydrogen atom on its α carbon atom is in equilibrium with its corresponding enol isomer. The spontaneous inter-conversion between two isomers usually with the change in position of a hydrogen is called tautomerism. The individual keto and enol isomers are called tautomers.

To give:

The enol tautomer of cyclopentanone shown.

Interpretation Introduction

b)

Interpretation:

The enol tautomer of Methyl thioacetate shown is to be given.

Concept introduction:

A carbonyl compound with a hydrogen atom on its α carbon atom is in equilibrium with its corresponding enol isomer. The spontaneous inter-conversion between two isomers usually with the change in position of a hydrogen is called tautomerism. The individual keto and enol isomers are called tautomers.

To give:

The enol tautomer of Methyl thioacetate shown.

Interpretation Introduction

c)

Interpretation:

The enol tautomer of Ethyl acetate shown is to be given.

Concept introduction:

A carbonyl compound with a hydrogen atom on its α carbon atom is in equilibrium with its corresponding enol isomer. The spontaneous inter-conversion between two isomers usually with the change in position of a hydrogen is called tautomerism. The individual keto and enol isomers are called tautomers.

To give:

The enol tautomer of Ethyl acetate shown.

Interpretation Introduction

d)

Interpretation:

The enol tautomer of Propanal shown is to be given.

Concept introduction:

A carbonyl compound with a hydrogen atom on its α carbon atom is in equilibrium with its corresponding enol isomer. The spontaneous inter-conversion between two isomers usually with the change in position of a hydrogen is called tautomerism. The individual keto and enol isomers are called tautomers.

To give:

The enol tautomer of Propanal shown.

Interpretation Introduction

e)

Interpretation:

The enol tautomer of Acetic acid shown is to be given.

Concept introduction:

A carbonyl compound with a hydrogen atom on its α carbon atom is in equilibrium with its corresponding enol isomer. The spontaneous inter-conversion between two isomers usually with the change in position of a hydrogen is called tautomerism. The individual keto and enol isomers are called tautomers.

To give:

The enol tautomer of Acetic acid shown.

Interpretation Introduction

f)

Interpretation:

The enol tautomer of Phenylacetone shown is to be given.

Concept introduction:

A carbonyl compound with a hydrogen atom on its α carbon atom is in equilibrium with its corresponding enol isomer. The spontaneous inter-conversion between two isomers usually with the change in position of a hydrogen is called tautomerism. The individual keto and enol isomers are called tautomers.

To give:

The enol tautomer of Phenylaceton shown.

Answer 6

Chapter 22.1, Problem 1P

Interpretation Introduction

a)

Interpretation:

The enol tautomer of Cyclopentanone shown is to be given.

Concept introduction:

A carbonyl compound with a hydrogen atom on its α carbon atom is in equilibrium with its corresponding enol isomer. The spontaneous inter-conversion between two isomers usually with the change in position of a hydrogen is called tautomerism. The individual keto and enol isomers are called tautomers.

To give:

The enol tautomer of cyclopentanone shown.

Answer 7

Chapter 22.1, Problem 1P

Interpretation Introduction

a)

Interpretation:

The enol tautomer of Cyclopentanone shown is to be given.

Concept introduction:

A carbonyl compound with a hydrogen atom on its α carbon atom is in equilibrium with its corresponding enol isomer. The spontaneous inter-conversion between two isomers usually with the change in position of a hydrogen is called tautomerism. The individual keto and enol isomers are called tautomers.

To give:

The enol tautomer of cyclopentanone shown.

Answer 8

Interpretation Introduction

b)

Interpretation:

The enol tautomer of Methyl thioacetate shown is to be given.

Concept introduction:

A carbonyl compound with a hydrogen atom on its α carbon atom is in equilibrium with its corresponding enol isomer. The spontaneous inter-conversion between two isomers usually with the change in position of a hydrogen is called tautomerism. The individual keto and enol isomers are called tautomers.

To give:

The enol tautomer of Methyl thioacetate shown.

Answer 9

Interpretation Introduction

b)

Interpretation:

The enol tautomer of Methyl thioacetate shown is to be given.

Concept introduction:

A carbonyl compound with a hydrogen atom on its α carbon atom is in equilibrium with its corresponding enol isomer. The spontaneous inter-conversion between two isomers usually with the change in position of a hydrogen is called tautomerism. The individual keto and enol isomers are called tautomers.

To give:

The enol tautomer of Methyl thioacetate shown.

Answer 10

Interpretation Introduction

c)

Interpretation:

The enol tautomer of Ethyl acetate shown is to be given.

Concept introduction:

A carbonyl compound with a hydrogen atom on its α carbon atom is in equilibrium with its corresponding enol isomer. The spontaneous inter-conversion between two isomers usually with the change in position of a hydrogen is called tautomerism. The individual keto and enol isomers are called tautomers.

To give:

The enol tautomer of Ethyl acetate shown.

Answer 11

Interpretation Introduction

c)

Interpretation:

The enol tautomer of Ethyl acetate shown is to be given.

Concept introduction:

A carbonyl compound with a hydrogen atom on its α carbon atom is in equilibrium with its corresponding enol isomer. The spontaneous inter-conversion between two isomers usually with the change in position of a hydrogen is called tautomerism. The individual keto and enol isomers are called tautomers.

To give:

The enol tautomer of Ethyl acetate shown.

Answer 12

Interpretation Introduction

d)

Interpretation:

The enol tautomer of Propanal shown is to be given.

Concept introduction:

A carbonyl compound with a hydrogen atom on its α carbon atom is in equilibrium with its corresponding enol isomer. The spontaneous inter-conversion between two isomers usually with the change in position of a hydrogen is called tautomerism. The individual keto and enol isomers are called tautomers.

To give:

The enol tautomer of Propanal shown.

Answer 13

Interpretation Introduction

d)

Interpretation:

The enol tautomer of Propanal shown is to be given.

Concept introduction:

A carbonyl compound with a hydrogen atom on its α carbon atom is in equilibrium with its corresponding enol isomer. The spontaneous inter-conversion between two isomers usually with the change in position of a hydrogen is called tautomerism. The individual keto and enol isomers are called tautomers.

To give:

The enol tautomer of Propanal shown.

Answer 14

Interpretation Introduction

e)

Interpretation:

The enol tautomer of Acetic acid shown is to be given.

Concept introduction:

A carbonyl compound with a hydrogen atom on its α carbon atom is in equilibrium with its corresponding enol isomer. The spontaneous inter-conversion between two isomers usually with the change in position of a hydrogen is called tautomerism. The individual keto and enol isomers are called tautomers.

To give:

The enol tautomer of Acetic acid shown.

Answer 15

Interpretation Introduction

e)

Interpretation:

The enol tautomer of Acetic acid shown is to be given.

Concept introduction:

A carbonyl compound with a hydrogen atom on its α carbon atom is in equilibrium with its corresponding enol isomer. The spontaneous inter-conversion between two isomers usually with the change in position of a hydrogen is called tautomerism. The individual keto and enol isomers are called tautomers.

To give:

The enol tautomer of Acetic acid shown.

Answer 16

Interpretation Introduction

f)

Interpretation:

The enol tautomer of Phenylacetone shown is to be given.

Concept introduction:

A carbonyl compound with a hydrogen atom on its α carbon atom is in equilibrium with its corresponding enol isomer. The spontaneous inter-conversion between two isomers usually with the change in position of a hydrogen is called tautomerism. The individual keto and enol isomers are called tautomers.

To give:

The enol tautomer of Phenylaceton shown.

Answer 17

Interpretation Introduction

f)

Interpretation:

The enol tautomer of Phenylacetone shown is to be given.

Concept introduction:

A carbonyl compound with a hydrogen atom on its α carbon atom is in equilibrium with its corresponding enol isomer. The spontaneous inter-conversion between two isomers usually with the change in position of a hydrogen is called tautomerism. The individual keto and enol isomers are called tautomers.

To give:

The enol tautomer of Phenylaceton shown.

Answer 18

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Answer 29

Ch. 22.1 - Prob. 1P Ch. 22.1 - How many acidic hydrogens does each of the...Ch. 22.1 - Prob. 3P Ch. 22.3 - Write the complete mechanism for the deuteration...Ch. 22.3 - Prob. 5P Ch. 22.4 - If methanol rather than water is added at the end...Ch. 22.5 - Prob. 7P Ch. 22.5 - Draw a resonance structure of the acetonitrile...Ch. 22.6 - If methanol rather than water is added at the end...Ch. 22.7 - Prob. 10P

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