(a) Interpretation: The carbonyl compound and amine or alcohol needed to prepare the given compound are to be predicted. Concept introduction: A carbonyl compound ( aldehyde or ketone ) reacts with 1 ° amine to yield imine, and reacts with 2 ° amine to yield enamine. The mechanism of both reactions are identical except for the last step. The last step for enamine formation involves loss of a proton from the adjacent C − H bond, whereas the last step for imine formation involves loss of a proton from the N atom itself.

Question

Propose a synthesis pathway for the following transformations. b) c) d)

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 21, Problem 21.58P

Interpretation Introduction

(a)

Interpretation:

The carbonyl compound and amine or alcohol needed to prepare the given compound are to be predicted.

Concept introduction:

A carbonyl compound (aldehyde or ketone) reacts with 1° amine to yield imine, and reacts with 2° amine to yield enamine. The mechanism of both reactions are identical except for the last step. The last step for enamine formation involves loss of a proton from the adjacent C−H bond, whereas the last step for imine formation involves loss of a proton from the N atom itself.

Interpretation Introduction

(b)

Interpretation:

The carbonyl compound and amine or alcohol needed to prepare the given compound are to be predicted.

Concept introduction:

A carbonyl compound (aldehyde or ketone) reacts with 1° amine to yield imine, and reacts with 2° amine to yield enamine. The mechanism of both reactions are identical except for the last step. The last step for enamine formation involves loss of a proton from the adjacent C−H bond, whereas the last step for imine formation involves loss of a proton from the N atom itself.

Interpretation Introduction

(c)

Interpretation:

The carbonyl compound and amine or alcohol needed to prepare the given compound are to be predicted.

Concept introduction:

Acetals are the groups in which carbon atom is bonded with two OR groups through single bonds. A carbonyl compound (aldehyde or ketone) yields an acetal, when it is treated with two equivalents of an alcohol or one equivalent of diol in the presence of strong acid. The reaction is reversible.

Interpretation Introduction

(d)

Interpretation:

The carbonyl compound and amine or alcohol needed to prepare the given compound are to be predicted.

Concept introduction:

Acetals are the groups in which carbon atom is bonded with two OR groups through single bonds. A carbonyl compound (aldehyde or ketone) yields an acetal, when it is treated with two equivalents of an alcohol or one equivalent of diol in the presence of strong acid. The reaction is reversible.

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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 21, Problem 21.58P

Interpretation Introduction

(a)

Interpretation:

The carbonyl compound and amine or alcohol needed to prepare the given compound are to be predicted.

Concept introduction:

A carbonyl compound (aldehyde or ketone) reacts with 1° amine to yield imine, and reacts with 2° amine to yield enamine. The mechanism of both reactions are identical except for the last step. The last step for enamine formation involves loss of a proton from the adjacent C−H bond, whereas the last step for imine formation involves loss of a proton from the N atom itself.

Interpretation Introduction

(b)

Interpretation:

The carbonyl compound and amine or alcohol needed to prepare the given compound are to be predicted.

Concept introduction:

A carbonyl compound (aldehyde or ketone) reacts with 1° amine to yield imine, and reacts with 2° amine to yield enamine. The mechanism of both reactions are identical except for the last step. The last step for enamine formation involves loss of a proton from the adjacent C−H bond, whereas the last step for imine formation involves loss of a proton from the N atom itself.

Interpretation Introduction

(c)

Interpretation:

The carbonyl compound and amine or alcohol needed to prepare the given compound are to be predicted.

Concept introduction:

Acetals are the groups in which carbon atom is bonded with two OR groups through single bonds. A carbonyl compound (aldehyde or ketone) yields an acetal, when it is treated with two equivalents of an alcohol or one equivalent of diol in the presence of strong acid. The reaction is reversible.

Interpretation Introduction

(d)

Interpretation:

The carbonyl compound and amine or alcohol needed to prepare the given compound are to be predicted.

Concept introduction:

Acetals are the groups in which carbon atom is bonded with two OR groups through single bonds. A carbonyl compound (aldehyde or ketone) yields an acetal, when it is treated with two equivalents of an alcohol or one equivalent of diol in the presence of strong acid. The reaction is reversible.

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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 21, Problem 21.58P

Interpretation Introduction

(a)

Interpretation:

The carbonyl compound and amine or alcohol needed to prepare the given compound are to be predicted.

Concept introduction:

A carbonyl compound (aldehyde or ketone) reacts with 1° amine to yield imine, and reacts with 2° amine to yield enamine. The mechanism of both reactions are identical except for the last step. The last step for enamine formation involves loss of a proton from the adjacent C−H bond, whereas the last step for imine formation involves loss of a proton from the N atom itself.

Interpretation Introduction

(b)

Interpretation:

The carbonyl compound and amine or alcohol needed to prepare the given compound are to be predicted.

Concept introduction:

A carbonyl compound (aldehyde or ketone) reacts with 1° amine to yield imine, and reacts with 2° amine to yield enamine. The mechanism of both reactions are identical except for the last step. The last step for enamine formation involves loss of a proton from the adjacent C−H bond, whereas the last step for imine formation involves loss of a proton from the N atom itself.

Interpretation Introduction

(c)

Interpretation:

The carbonyl compound and amine or alcohol needed to prepare the given compound are to be predicted.

Concept introduction:

Acetals are the groups in which carbon atom is bonded with two OR groups through single bonds. A carbonyl compound (aldehyde or ketone) yields an acetal, when it is treated with two equivalents of an alcohol or one equivalent of diol in the presence of strong acid. The reaction is reversible.

Interpretation Introduction

(d)

Interpretation:

The carbonyl compound and amine or alcohol needed to prepare the given compound are to be predicted.

Concept introduction:

Acetals are the groups in which carbon atom is bonded with two OR groups through single bonds. A carbonyl compound (aldehyde or ketone) yields an acetal, when it is treated with two equivalents of an alcohol or one equivalent of diol in the presence of strong acid. The reaction is reversible.

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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 21, Problem 21.58P

Interpretation Introduction

(a)

Interpretation:

The carbonyl compound and amine or alcohol needed to prepare the given compound are to be predicted.

Concept introduction:

A carbonyl compound (aldehyde or ketone) reacts with 1° amine to yield imine, and reacts with 2° amine to yield enamine. The mechanism of both reactions are identical except for the last step. The last step for enamine formation involves loss of a proton from the adjacent C−H bond, whereas the last step for imine formation involves loss of a proton from the N atom itself.

Interpretation Introduction

(b)

Interpretation:

The carbonyl compound and amine or alcohol needed to prepare the given compound are to be predicted.

Concept introduction:

A carbonyl compound (aldehyde or ketone) reacts with 1° amine to yield imine, and reacts with 2° amine to yield enamine. The mechanism of both reactions are identical except for the last step. The last step for enamine formation involves loss of a proton from the adjacent C−H bond, whereas the last step for imine formation involves loss of a proton from the N atom itself.

Interpretation Introduction

(c)

Interpretation:

The carbonyl compound and amine or alcohol needed to prepare the given compound are to be predicted.

Concept introduction:

Acetals are the groups in which carbon atom is bonded with two OR groups through single bonds. A carbonyl compound (aldehyde or ketone) yields an acetal, when it is treated with two equivalents of an alcohol or one equivalent of diol in the presence of strong acid. The reaction is reversible.

Interpretation Introduction

(d)

Interpretation:

The carbonyl compound and amine or alcohol needed to prepare the given compound are to be predicted.

Concept introduction:

Acetals are the groups in which carbon atom is bonded with two OR groups through single bonds. A carbonyl compound (aldehyde or ketone) yields an acetal, when it is treated with two equivalents of an alcohol or one equivalent of diol in the presence of strong acid. The reaction is reversible.

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Answer 5

Chapter 21, Problem 21.58P

Interpretation Introduction

(a)

Interpretation:

The carbonyl compound and amine or alcohol needed to prepare the given compound are to be predicted.

Concept introduction:

A carbonyl compound (aldehyde or ketone) reacts with 1° amine to yield imine, and reacts with 2° amine to yield enamine. The mechanism of both reactions are identical except for the last step. The last step for enamine formation involves loss of a proton from the adjacent C−H bond, whereas the last step for imine formation involves loss of a proton from the N atom itself.

Interpretation Introduction

(b)

Interpretation:

The carbonyl compound and amine or alcohol needed to prepare the given compound are to be predicted.

Concept introduction:

A carbonyl compound (aldehyde or ketone) reacts with 1° amine to yield imine, and reacts with 2° amine to yield enamine. The mechanism of both reactions are identical except for the last step. The last step for enamine formation involves loss of a proton from the adjacent C−H bond, whereas the last step for imine formation involves loss of a proton from the N atom itself.

Interpretation Introduction

(c)

Interpretation:

The carbonyl compound and amine or alcohol needed to prepare the given compound are to be predicted.

Concept introduction:

Acetals are the groups in which carbon atom is bonded with two OR groups through single bonds. A carbonyl compound (aldehyde or ketone) yields an acetal, when it is treated with two equivalents of an alcohol or one equivalent of diol in the presence of strong acid. The reaction is reversible.

Interpretation Introduction

(d)

Interpretation:

The carbonyl compound and amine or alcohol needed to prepare the given compound are to be predicted.

Concept introduction:

Acetals are the groups in which carbon atom is bonded with two OR groups through single bonds. A carbonyl compound (aldehyde or ketone) yields an acetal, when it is treated with two equivalents of an alcohol or one equivalent of diol in the presence of strong acid. The reaction is reversible.

Answer 6

Chapter 21, Problem 21.58P

Interpretation Introduction

(a)

Interpretation:

The carbonyl compound and amine or alcohol needed to prepare the given compound are to be predicted.

Concept introduction:

A carbonyl compound (aldehyde or ketone) reacts with 1° amine to yield imine, and reacts with 2° amine to yield enamine. The mechanism of both reactions are identical except for the last step. The last step for enamine formation involves loss of a proton from the adjacent C−H bond, whereas the last step for imine formation involves loss of a proton from the N atom itself.

Answer 7

Chapter 21, Problem 21.58P

Interpretation Introduction

(a)

Interpretation:

The carbonyl compound and amine or alcohol needed to prepare the given compound are to be predicted.

Concept introduction:

A carbonyl compound (aldehyde or ketone) reacts with 1° amine to yield imine, and reacts with 2° amine to yield enamine. The mechanism of both reactions are identical except for the last step. The last step for enamine formation involves loss of a proton from the adjacent C−H bond, whereas the last step for imine formation involves loss of a proton from the N atom itself.

Answer 8

Interpretation Introduction

(b)

Interpretation:

The carbonyl compound and amine or alcohol needed to prepare the given compound are to be predicted.

Concept introduction:

A carbonyl compound (aldehyde or ketone) reacts with 1° amine to yield imine, and reacts with 2° amine to yield enamine. The mechanism of both reactions are identical except for the last step. The last step for enamine formation involves loss of a proton from the adjacent C−H bond, whereas the last step for imine formation involves loss of a proton from the N atom itself.

Answer 9

Interpretation Introduction

(b)

Interpretation:

The carbonyl compound and amine or alcohol needed to prepare the given compound are to be predicted.

Concept introduction:

A carbonyl compound (aldehyde or ketone) reacts with 1° amine to yield imine, and reacts with 2° amine to yield enamine. The mechanism of both reactions are identical except for the last step. The last step for enamine formation involves loss of a proton from the adjacent C−H bond, whereas the last step for imine formation involves loss of a proton from the N atom itself.

Answer 10

Interpretation Introduction

(c)

Interpretation:

The carbonyl compound and amine or alcohol needed to prepare the given compound are to be predicted.

Concept introduction:

Acetals are the groups in which carbon atom is bonded with two OR groups through single bonds. A carbonyl compound (aldehyde or ketone) yields an acetal, when it is treated with two equivalents of an alcohol or one equivalent of diol in the presence of strong acid. The reaction is reversible.

Answer 11

Interpretation Introduction

(c)

Interpretation:

The carbonyl compound and amine or alcohol needed to prepare the given compound are to be predicted.

Concept introduction:

Acetals are the groups in which carbon atom is bonded with two OR groups through single bonds. A carbonyl compound (aldehyde or ketone) yields an acetal, when it is treated with two equivalents of an alcohol or one equivalent of diol in the presence of strong acid. The reaction is reversible.

Answer 12

Interpretation Introduction

(d)

Interpretation:

The carbonyl compound and amine or alcohol needed to prepare the given compound are to be predicted.

Concept introduction:

Acetals are the groups in which carbon atom is bonded with two OR groups through single bonds. A carbonyl compound (aldehyde or ketone) yields an acetal, when it is treated with two equivalents of an alcohol or one equivalent of diol in the presence of strong acid. The reaction is reversible.

Answer 13

Interpretation Introduction

(d)

Interpretation:

The carbonyl compound and amine or alcohol needed to prepare the given compound are to be predicted.

Concept introduction:

Acetals are the groups in which carbon atom is bonded with two OR groups through single bonds. A carbonyl compound (aldehyde or ketone) yields an acetal, when it is treated with two equivalents of an alcohol or one equivalent of diol in the presence of strong acid. The reaction is reversible.

Answer 14

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Answer 25

Ch. 21 - Rank the following compounds in order of...Ch. 21 - Prob. 21.2P Ch. 21 - Give the IUPAC name for each aldehyde.Ch. 21 - Prob. 21.4P Ch. 21 - Give the IUPAC name for each ketone.Ch. 21 - Prob. 21.6P Ch. 21 - Prob. 21.7P Ch. 21 - The boiling point of is significantly higher than...Ch. 21 - Which carbonyl group in each pair absorbs at a...Ch. 21 - Problem 21.10 Draw the structure of all...

Solution Summary: The author explains that the carbonyl compound and the amine or alcohol needed to prepare the given compound are to be predicted.

Chapter 21 Solutions