a) Interpretation: The products formed in the reaction given are to be identified. The mechanism of the reaction also is to be provided. Concept introduction: Aldehydes and ketones react with hydroxyl amine to produce an oxime by eliminating a molecule of water. To identify: The products formed in the reaction given and to provide the mechanism of the reaction.

Question

: Treatment of (CHa)CHCH(OH)CH,CH3 with TSOH affords two products (M and N) with molecular formula CgH12. The 'H NMR spectra of M and N are given below. Propose structures for M and N and draw a mechanism to explain their formation. 1H NMR of M 3H 1H NMR of N 3H 3H 3 H 1H 3 H 2 H 2H 2H 8 7 6 4 1 0 9 8. 2 1 ppm ppm 4.

Answer 1

Question

Definition Definition Organic compounds that have a carbonyl group, C=O, as their functional group. The carbonyl group in aldehydes is placed at the end of the molecular structure, which means the C=O is attached to one hydrogen atom and an alkyl group or a benzene ring. Just like all the other homologous series in organic chemistry, the naming of aldehydes uses the suffix “-al”. The general molecular formula is C n H 2n O.

Chapter 19.SE, Problem 34MP

Interpretation Introduction

a)

Interpretation:

The products formed in the reaction given are to be identified. The mechanism of the reaction also is to be provided.

Concept introduction:

Aldehydes and ketones react with hydroxyl amine to produce an oxime by eliminating a molecule of water.

To identify:

The products formed in the reaction given and to provide the mechanism of the reaction.

Interpretation Introduction

b)

Interpretation:

The products formed in the reaction given are to be identified. The mechanism of the reaction also is to be provided.

Concept introduction:

Ketones react wih secondary amines to yield an enamine as the product by eliminating a molecule of water.

To identify:

The products formed in the reaction given and to provide the mechanism of the reaction.

Interpretation Introduction

c)

Interpretation:

The products formed in the reaction given are to be identified. The mechanism of the reaction also is to be provided.

Concept introduction:

Ketones react wih primary amines to yield an imine as the product by eliminating a molecule of water.

To identify:

The products formed in the reaction given and to provide the mechanism of the reaction.

Interpretation Introduction

d)

Interpretation:

The products formed in the reaction given are to be identified. The mechanism of the reaction also is to be provided.

Concept introduction:

Ketones react wih secondary amines to yield an enamine as the product by eliminating a molecule of water.

To identify:

The products formed in the reaction given and to provide the mechanism of the reaction.

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: Treatment of (CHa)CHCH(OH)CH,CH3 with TSOH affords two products (M and N) with molecular formula CgH12. The 'H NMR spectra of M and N are given below. Propose structures for M and N and draw a mechanism to explain their formation. 1H NMR of M 3H 1H NMR of N 3H 3H 3 H 1H 3 H 2 H 2H 2H 8 7 6 4 1 0 9 8. 2 1 ppm ppm 4.

Predict the product(s) and provide a mechanism:

Predict the product(s) and provide the mechanism. d Br for

Answer 2

Question

Definition Definition Organic compounds that have a carbonyl group, C=O, as their functional group. The carbonyl group in aldehydes is placed at the end of the molecular structure, which means the C=O is attached to one hydrogen atom and an alkyl group or a benzene ring. Just like all the other homologous series in organic chemistry, the naming of aldehydes uses the suffix “-al”. The general molecular formula is C n H 2n O.

Chapter 19.SE, Problem 34MP

Interpretation Introduction

a)

Interpretation:

The products formed in the reaction given are to be identified. The mechanism of the reaction also is to be provided.

Concept introduction:

Aldehydes and ketones react with hydroxyl amine to produce an oxime by eliminating a molecule of water.

To identify:

The products formed in the reaction given and to provide the mechanism of the reaction.

Interpretation Introduction

b)

Interpretation:

The products formed in the reaction given are to be identified. The mechanism of the reaction also is to be provided.

Concept introduction:

Ketones react wih secondary amines to yield an enamine as the product by eliminating a molecule of water.

To identify:

The products formed in the reaction given and to provide the mechanism of the reaction.

Interpretation Introduction

c)

Interpretation:

The products formed in the reaction given are to be identified. The mechanism of the reaction also is to be provided.

Concept introduction:

Ketones react wih primary amines to yield an imine as the product by eliminating a molecule of water.

To identify:

The products formed in the reaction given and to provide the mechanism of the reaction.

Interpretation Introduction

d)

Interpretation:

The products formed in the reaction given are to be identified. The mechanism of the reaction also is to be provided.

Concept introduction:

Ketones react wih secondary amines to yield an enamine as the product by eliminating a molecule of water.

To identify:

The products formed in the reaction given and to provide the mechanism of the reaction.

Expert Solution & Answer

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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 aldehydes is placed at the end of the molecular structure, which means the C=O is attached to one hydrogen atom and an alkyl group or a benzene ring. Just like all the other homologous series in organic chemistry, the naming of aldehydes uses the suffix “-al”. The general molecular formula is C n H 2n O.

Chapter 19.SE, Problem 34MP

Interpretation Introduction

a)

Interpretation:

The products formed in the reaction given are to be identified. The mechanism of the reaction also is to be provided.

Concept introduction:

Aldehydes and ketones react with hydroxyl amine to produce an oxime by eliminating a molecule of water.

To identify:

The products formed in the reaction given and to provide the mechanism of the reaction.

Interpretation Introduction

b)

Interpretation:

The products formed in the reaction given are to be identified. The mechanism of the reaction also is to be provided.

Concept introduction:

Ketones react wih secondary amines to yield an enamine as the product by eliminating a molecule of water.

To identify:

The products formed in the reaction given and to provide the mechanism of the reaction.

Interpretation Introduction

c)

Interpretation:

The products formed in the reaction given are to be identified. The mechanism of the reaction also is to be provided.

Concept introduction:

Ketones react wih primary amines to yield an imine as the product by eliminating a molecule of water.

To identify:

The products formed in the reaction given and to provide the mechanism of the reaction.

Interpretation Introduction

d)

Interpretation:

The products formed in the reaction given are to be identified. The mechanism of the reaction also is to be provided.

Concept introduction:

Ketones react wih secondary amines to yield an enamine as the product by eliminating a molecule of water.

To identify:

The products formed in the reaction given and to provide the mechanism of the reaction.

Expert Solution & Answer

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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 aldehydes is placed at the end of the molecular structure, which means the C=O is attached to one hydrogen atom and an alkyl group or a benzene ring. Just like all the other homologous series in organic chemistry, the naming of aldehydes uses the suffix “-al”. The general molecular formula is C n H 2n O.

Chapter 19.SE, Problem 34MP

Interpretation Introduction

a)

Interpretation:

The products formed in the reaction given are to be identified. The mechanism of the reaction also is to be provided.

Concept introduction:

Aldehydes and ketones react with hydroxyl amine to produce an oxime by eliminating a molecule of water.

To identify:

The products formed in the reaction given and to provide the mechanism of the reaction.

Interpretation Introduction

b)

Interpretation:

The products formed in the reaction given are to be identified. The mechanism of the reaction also is to be provided.

Concept introduction:

Ketones react wih secondary amines to yield an enamine as the product by eliminating a molecule of water.

To identify:

The products formed in the reaction given and to provide the mechanism of the reaction.

Interpretation Introduction

c)

Interpretation:

The products formed in the reaction given are to be identified. The mechanism of the reaction also is to be provided.

Concept introduction:

Ketones react wih primary amines to yield an imine as the product by eliminating a molecule of water.

To identify:

The products formed in the reaction given and to provide the mechanism of the reaction.

Interpretation Introduction

d)

Interpretation:

The products formed in the reaction given are to be identified. The mechanism of the reaction also is to be provided.

Concept introduction:

Ketones react wih secondary amines to yield an enamine as the product by eliminating a molecule of water.

To identify:

The products formed in the reaction given and to provide the mechanism of the reaction.

Expert Solution & Answer

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Answer 5

Chapter 19.SE, Problem 34MP

Interpretation Introduction

a)

Interpretation:

The products formed in the reaction given are to be identified. The mechanism of the reaction also is to be provided.

Concept introduction:

Aldehydes and ketones react with hydroxyl amine to produce an oxime by eliminating a molecule of water.

To identify:

The products formed in the reaction given and to provide the mechanism of the reaction.

Interpretation Introduction

b)

Interpretation:

The products formed in the reaction given are to be identified. The mechanism of the reaction also is to be provided.

Concept introduction:

Ketones react wih secondary amines to yield an enamine as the product by eliminating a molecule of water.

To identify:

The products formed in the reaction given and to provide the mechanism of the reaction.

Interpretation Introduction

c)

Interpretation:

The products formed in the reaction given are to be identified. The mechanism of the reaction also is to be provided.

Concept introduction:

Ketones react wih primary amines to yield an imine as the product by eliminating a molecule of water.

To identify:

The products formed in the reaction given and to provide the mechanism of the reaction.

Interpretation Introduction

d)

Interpretation:

The products formed in the reaction given are to be identified. The mechanism of the reaction also is to be provided.

Concept introduction:

Ketones react wih secondary amines to yield an enamine as the product by eliminating a molecule of water.

To identify:

The products formed in the reaction given and to provide the mechanism of the reaction.

Answer 6

Chapter 19.SE, Problem 34MP

Interpretation Introduction

a)

Interpretation:

The products formed in the reaction given are to be identified. The mechanism of the reaction also is to be provided.

Concept introduction:

Aldehydes and ketones react with hydroxyl amine to produce an oxime by eliminating a molecule of water.

To identify:

The products formed in the reaction given and to provide the mechanism of the reaction.

Answer 7

Chapter 19.SE, Problem 34MP

Interpretation Introduction

a)

Interpretation:

The products formed in the reaction given are to be identified. The mechanism of the reaction also is to be provided.

Concept introduction:

Aldehydes and ketones react with hydroxyl amine to produce an oxime by eliminating a molecule of water.

To identify:

The products formed in the reaction given and to provide the mechanism of the reaction.

Answer 8

Interpretation Introduction

b)

Interpretation:

The products formed in the reaction given are to be identified. The mechanism of the reaction also is to be provided.

Concept introduction:

Ketones react wih secondary amines to yield an enamine as the product by eliminating a molecule of water.

To identify:

The products formed in the reaction given and to provide the mechanism of the reaction.

Answer 9

Interpretation Introduction

b)

Interpretation:

The products formed in the reaction given are to be identified. The mechanism of the reaction also is to be provided.

Concept introduction:

Ketones react wih secondary amines to yield an enamine as the product by eliminating a molecule of water.

To identify:

The products formed in the reaction given and to provide the mechanism of the reaction.

Answer 10

Interpretation Introduction

c)

Interpretation:

The products formed in the reaction given are to be identified. The mechanism of the reaction also is to be provided.

Concept introduction:

Ketones react wih primary amines to yield an imine as the product by eliminating a molecule of water.

To identify:

The products formed in the reaction given and to provide the mechanism of the reaction.

Answer 11

Interpretation Introduction

c)

Interpretation:

The products formed in the reaction given are to be identified. The mechanism of the reaction also is to be provided.

Concept introduction:

Ketones react wih primary amines to yield an imine as the product by eliminating a molecule of water.

To identify:

The products formed in the reaction given and to provide the mechanism of the reaction.

Answer 12

Interpretation Introduction

d)

Interpretation:

The products formed in the reaction given are to be identified. The mechanism of the reaction also is to be provided.

Concept introduction:

Ketones react wih secondary amines to yield an enamine as the product by eliminating a molecule of water.

To identify:

The products formed in the reaction given and to provide the mechanism of the reaction.

Answer 13

Interpretation Introduction

d)

Interpretation:

The products formed in the reaction given are to be identified. The mechanism of the reaction also is to be provided.

Concept introduction:

Ketones react wih secondary amines to yield an enamine as the product by eliminating a molecule of water.

To identify:

The products formed in the reaction given and to provide the mechanism of the reaction.

Answer 14

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Answer 25

Ch. 19.1 - Prob. 1P Ch. 19.1 - Draw structures corresponding to the following...Ch. 19.2 - Prob. 3P Ch. 19.2 - How would you carry out the following reactions?...Ch. 19.4 - Treatment of an aldehyde or ketone with cyanide...Ch. 19.4 - p-Nitrobenzaldehyde is more reactive toward...Ch. 19.5 - Prob. 7P Ch. 19.5 - The oxygen in water is primarily (99.8) 16O, but...Ch. 19.6 - Prob. 9P Ch. 19.8 - Show the products you would obtain by...

Solution Summary: The author explains how aldehydes and ketones react with hydroxyl amine to produce an oxime by eliminating a water molecule.

Chapter 19 Solutions