(a) Interpretation: The curved arrow mechanism for the racemization process given in Eq 22.19 is to be shown. Concept introduction: Racemic mixture is the mixture of a compound which is optically inactive because half the molecules are the mirror image of other half. Racemization of a ketone involves enol as an intermediate. Enol form has carbon-carbon double bond which is planar and can be attacked from either above or below the plane. When solvent molecule attacks enol, then both the enantiomers are formed giving a racemic mixture.

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Answer 1

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Definition Definition Organic compounds that have a carbonyl group, C = O, as their functional group. The carbonyl group in ketones is placed somewhere in the middle of the molecular structure, which means, the C=O is attached to two alkyl groups or benzene rings. Just like all other homologous series, the naming of ketones is done using a common suffix “-one”. The general molecular formula is C n H 2n O. Functional group of a ketone

Chapter 22, Problem 22.11P

Interpretation Introduction

(a)

Interpretation:

The curved arrow mechanism for the racemization process given in Eq 22.19 is to be shown.

Concept introduction:

Racemic mixture is the mixture of a compound which is optically inactive because half the molecules are the mirror image of other half. Racemization of a ketone involves enol as an intermediate. Enol form has carbon-carbon double bond which is planar and can be attacked from either above or below the plane. When solvent molecule attacks enol, then both the enantiomers are formed giving a racemic mixture.

Interpretation Introduction

(b)

Interpretation:

The curved arrow mechanism for the deuterium exchange given in Eq.22.18 is to be shown.

Concept Introduction:

The deuterium exchange reaction given involves keto-enol tautomerism. First the ketone gets converted into the enol form then again the enol takes deuterium from the solvent molecule and form the deuterated product.

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Predict the major products of this organic reaction: 1. LDA (-78°C) ? 2. Br Some notes: • Draw only the major product, or products. You can draw them in any arrangement you like. . • Be sure to use wedge and dash bonds where necessary, for example to distinguish between major products that are enantiomers. • If there are no products, just check the box under the drawing area. No reaction. Click and drag to start drawing a structure. X

Please draw the structures

Draw the missing intermediates 1 and 2, plus the final product 3, of this synthesis: 0 1. Eto 1. Eto- 1 2 2. MeBr 2. EtBr H3O+ A 3 You can draw the three structures in any arrangement you like. Explanation Check Click and drag to start drawing a structure.

Answer 2

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Definition Definition Organic compounds that have a carbonyl group, C = O, as their functional group. The carbonyl group in ketones is placed somewhere in the middle of the molecular structure, which means, the C=O is attached to two alkyl groups or benzene rings. Just like all other homologous series, the naming of ketones is done using a common suffix “-one”. The general molecular formula is C n H 2n O. Functional group of a ketone

Chapter 22, Problem 22.11P

Interpretation Introduction

(a)

Interpretation:

The curved arrow mechanism for the racemization process given in Eq 22.19 is to be shown.

Concept introduction:

Racemic mixture is the mixture of a compound which is optically inactive because half the molecules are the mirror image of other half. Racemization of a ketone involves enol as an intermediate. Enol form has carbon-carbon double bond which is planar and can be attacked from either above or below the plane. When solvent molecule attacks enol, then both the enantiomers are formed giving a racemic mixture.

Interpretation Introduction

(b)

Interpretation:

The curved arrow mechanism for the deuterium exchange given in Eq.22.18 is to be shown.

Concept Introduction:

The deuterium exchange reaction given involves keto-enol tautomerism. First the ketone gets converted into the enol form then again the enol takes deuterium from the solvent molecule and form the deuterated product.

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Answer 3

Question

Definition Definition Organic compounds that have a carbonyl group, C = O, as their functional group. The carbonyl group in ketones is placed somewhere in the middle of the molecular structure, which means, the C=O is attached to two alkyl groups or benzene rings. Just like all other homologous series, the naming of ketones is done using a common suffix “-one”. The general molecular formula is C n H 2n O. Functional group of a ketone

Chapter 22, Problem 22.11P

Interpretation Introduction

(a)

Interpretation:

The curved arrow mechanism for the racemization process given in Eq 22.19 is to be shown.

Concept introduction:

Racemic mixture is the mixture of a compound which is optically inactive because half the molecules are the mirror image of other half. Racemization of a ketone involves enol as an intermediate. Enol form has carbon-carbon double bond which is planar and can be attacked from either above or below the plane. When solvent molecule attacks enol, then both the enantiomers are formed giving a racemic mixture.

Interpretation Introduction

(b)

Interpretation:

The curved arrow mechanism for the deuterium exchange given in Eq.22.18 is to be shown.

Concept Introduction:

The deuterium exchange reaction given involves keto-enol tautomerism. First the ketone gets converted into the enol form then again the enol takes deuterium from the solvent molecule and form the deuterated product.

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Answer 4

Question

Definition Definition Organic compounds that have a carbonyl group, C = O, as their functional group. The carbonyl group in ketones is placed somewhere in the middle of the molecular structure, which means, the C=O is attached to two alkyl groups or benzene rings. Just like all other homologous series, the naming of ketones is done using a common suffix “-one”. The general molecular formula is C n H 2n O. Functional group of a ketone

Chapter 22, Problem 22.11P

Interpretation Introduction

(a)

Interpretation:

The curved arrow mechanism for the racemization process given in Eq 22.19 is to be shown.

Concept introduction:

Racemic mixture is the mixture of a compound which is optically inactive because half the molecules are the mirror image of other half. Racemization of a ketone involves enol as an intermediate. Enol form has carbon-carbon double bond which is planar and can be attacked from either above or below the plane. When solvent molecule attacks enol, then both the enantiomers are formed giving a racemic mixture.

Interpretation Introduction

(b)

Interpretation:

The curved arrow mechanism for the deuterium exchange given in Eq.22.18 is to be shown.

Concept Introduction:

The deuterium exchange reaction given involves keto-enol tautomerism. First the ketone gets converted into the enol form then again the enol takes deuterium from the solvent molecule and form the deuterated product.

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Answer 5

Chapter 22, Problem 22.11P

Interpretation Introduction

(a)

Interpretation:

The curved arrow mechanism for the racemization process given in Eq 22.19 is to be shown.

Concept introduction:

Racemic mixture is the mixture of a compound which is optically inactive because half the molecules are the mirror image of other half. Racemization of a ketone involves enol as an intermediate. Enol form has carbon-carbon double bond which is planar and can be attacked from either above or below the plane. When solvent molecule attacks enol, then both the enantiomers are formed giving a racemic mixture.

Interpretation Introduction

(b)

Interpretation:

The curved arrow mechanism for the deuterium exchange given in Eq.22.18 is to be shown.

Concept Introduction:

The deuterium exchange reaction given involves keto-enol tautomerism. First the ketone gets converted into the enol form then again the enol takes deuterium from the solvent molecule and form the deuterated product.

Answer 6

Chapter 22, Problem 22.11P

Interpretation Introduction

(a)

Interpretation:

The curved arrow mechanism for the racemization process given in Eq 22.19 is to be shown.

Concept introduction:

Racemic mixture is the mixture of a compound which is optically inactive because half the molecules are the mirror image of other half. Racemization of a ketone involves enol as an intermediate. Enol form has carbon-carbon double bond which is planar and can be attacked from either above or below the plane. When solvent molecule attacks enol, then both the enantiomers are formed giving a racemic mixture.

Answer 7

Chapter 22, Problem 22.11P

Interpretation Introduction

(a)

Interpretation:

The curved arrow mechanism for the racemization process given in Eq 22.19 is to be shown.

Concept introduction:

Racemic mixture is the mixture of a compound which is optically inactive because half the molecules are the mirror image of other half. Racemization of a ketone involves enol as an intermediate. Enol form has carbon-carbon double bond which is planar and can be attacked from either above or below the plane. When solvent molecule attacks enol, then both the enantiomers are formed giving a racemic mixture.

Answer 8

Interpretation Introduction

(b)

Interpretation:

The curved arrow mechanism for the deuterium exchange given in Eq.22.18 is to be shown.

Concept Introduction:

The deuterium exchange reaction given involves keto-enol tautomerism. First the ketone gets converted into the enol form then again the enol takes deuterium from the solvent molecule and form the deuterated product.

Answer 9

Interpretation Introduction

(b)

Interpretation:

The curved arrow mechanism for the deuterium exchange given in Eq.22.18 is to be shown.

Concept Introduction:

The deuterium exchange reaction given involves keto-enol tautomerism. First the ketone gets converted into the enol form then again the enol takes deuterium from the solvent molecule and form the deuterated product.

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 the curved arrow mechanism for the racemization process in Eq.22.19.

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Chapter 22 Solutions