(a) Interpretation: How the given amine can be synthesized from a ketone or an aldehyde is to be shown. Concept introduction: Aldehydes and ketones react with ammonia and primary amines to form an imine. The reaction occurs as a nucleophilic addition of the amine to the carbonyl carbon followed by protonation and elimination of H 2 O under mildly acidic conditions. The imine can be reduced to the corresponding amine with NaBH 4 via nucleophilic addition of a hydride ion to the imine carbon.

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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 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 18, Problem 18.41P

Interpretation Introduction

(a)

Interpretation:

How the given amine can be synthesized from a ketone or an aldehyde is to be shown.

Concept introduction:

Aldehydes and ketones react with ammonia and primary amines to form an imine. The reaction occurs as a nucleophilic addition of the amine to the carbonyl carbon followed by protonation and elimination of H2O under mildly acidic conditions. The imine can be reduced to the corresponding amine with NaBH4 via nucleophilic addition of a hydride ion to the imine carbon.

Interpretation Introduction

(b)

Interpretation:

How the given amine can be synthesized from a ketone or an aldehyde is to be shown.

Concept introduction:

Aldehydes and ketones react with secondary amines to form an enamine. Since there is only one hydrogen attached to the nitrogen atom, imine formation cannot occur. Instead, a proton from the α-carbon is extracted to form an enamine. The reaction occurs as a nucleophilic addition of the amine to the carbonyl carbon followed by protonation and elimination of H2O under mildly acidic conditions. The enamine can be reduced to the corresponding amine with NaBH4 via the nucleophilic addition of a hydride ion to the imine carbon.

Interpretation Introduction

(c)

Interpretation:

Steps to synthesize amine from a ketone or aldehyde is to be proposed

Concept introduction:

Aldehydes and ketones react with ammonia and primary amines to form an imine. The reaction occurs as a nucleophilic addition of the amine to the carbonyl carbon followed by protonation and elimination of H2O under mildly acidic conditions. The imine can be reduced to the corresponding amine with NaBH4 via nucleophilic addition of a hydride ion to the imine carbon.

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a) Draw the mechanism for the reaction of a secondary amine with an acid chloride to make an amide.b) Explain what conditions (acid/basic/neutral; excess of one reagent, etc) are required to carry out this reaction in high yield, and why.

The reaction shown here is an example of the Favorskii reaction, which involves an R¯ leaving group in a nucleophilic addition-elimination reaction. (a) Draw the complete, detailed mechanism for this reaction and explain why R can act as a leaving NaOH H2O group. (b) Suggest how you can synthesize an ester from cyclopropanone using only this reaction.

Problem: (a) Fill in the missing starting material for the following reaction. (b) Draw the complete mechanism for the reaction. Don't forget to include any resonance structures! (c) Explain how you determined the starting material. H₂O H₂SO4 HO OH

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 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 18, Problem 18.41P

Interpretation Introduction

(a)

Interpretation:

How the given amine can be synthesized from a ketone or an aldehyde is to be shown.

Concept introduction:

Aldehydes and ketones react with ammonia and primary amines to form an imine. The reaction occurs as a nucleophilic addition of the amine to the carbonyl carbon followed by protonation and elimination of H2O under mildly acidic conditions. The imine can be reduced to the corresponding amine with NaBH4 via nucleophilic addition of a hydride ion to the imine carbon.

Interpretation Introduction

(b)

Interpretation:

How the given amine can be synthesized from a ketone or an aldehyde is to be shown.

Concept introduction:

Aldehydes and ketones react with secondary amines to form an enamine. Since there is only one hydrogen attached to the nitrogen atom, imine formation cannot occur. Instead, a proton from the α-carbon is extracted to form an enamine. The reaction occurs as a nucleophilic addition of the amine to the carbonyl carbon followed by protonation and elimination of H2O under mildly acidic conditions. The enamine can be reduced to the corresponding amine with NaBH4 via the nucleophilic addition of a hydride ion to the imine carbon.

Interpretation Introduction

(c)

Interpretation:

Steps to synthesize amine from a ketone or aldehyde is to be proposed

Concept introduction:

Aldehydes and ketones react with ammonia and primary amines to form an imine. The reaction occurs as a nucleophilic addition of the amine to the carbonyl carbon followed by protonation and elimination of H2O under mildly acidic conditions. The imine can be reduced to the corresponding amine with NaBH4 via nucleophilic addition of a hydride ion to the imine carbon.

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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 18, Problem 18.41P

Interpretation Introduction

(a)

Interpretation:

How the given amine can be synthesized from a ketone or an aldehyde is to be shown.

Concept introduction:

Aldehydes and ketones react with ammonia and primary amines to form an imine. The reaction occurs as a nucleophilic addition of the amine to the carbonyl carbon followed by protonation and elimination of H2O under mildly acidic conditions. The imine can be reduced to the corresponding amine with NaBH4 via nucleophilic addition of a hydride ion to the imine carbon.

Interpretation Introduction

(b)

Interpretation:

How the given amine can be synthesized from a ketone or an aldehyde is to be shown.

Concept introduction:

Aldehydes and ketones react with secondary amines to form an enamine. Since there is only one hydrogen attached to the nitrogen atom, imine formation cannot occur. Instead, a proton from the α-carbon is extracted to form an enamine. The reaction occurs as a nucleophilic addition of the amine to the carbonyl carbon followed by protonation and elimination of H2O under mildly acidic conditions. The enamine can be reduced to the corresponding amine with NaBH4 via the nucleophilic addition of a hydride ion to the imine carbon.

Interpretation Introduction

(c)

Interpretation:

Steps to synthesize amine from a ketone or aldehyde is to be proposed

Concept introduction:

Aldehydes and ketones react with ammonia and primary amines to form an imine. The reaction occurs as a nucleophilic addition of the amine to the carbonyl carbon followed by protonation and elimination of H2O under mildly acidic conditions. The imine can be reduced to the corresponding amine with NaBH4 via nucleophilic addition of a hydride ion to the imine carbon.

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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 18, Problem 18.41P

Interpretation Introduction

(a)

Interpretation:

How the given amine can be synthesized from a ketone or an aldehyde is to be shown.

Concept introduction:

Aldehydes and ketones react with ammonia and primary amines to form an imine. The reaction occurs as a nucleophilic addition of the amine to the carbonyl carbon followed by protonation and elimination of H2O under mildly acidic conditions. The imine can be reduced to the corresponding amine with NaBH4 via nucleophilic addition of a hydride ion to the imine carbon.

Interpretation Introduction

(b)

Interpretation:

How the given amine can be synthesized from a ketone or an aldehyde is to be shown.

Concept introduction:

Aldehydes and ketones react with secondary amines to form an enamine. Since there is only one hydrogen attached to the nitrogen atom, imine formation cannot occur. Instead, a proton from the α-carbon is extracted to form an enamine. The reaction occurs as a nucleophilic addition of the amine to the carbonyl carbon followed by protonation and elimination of H2O under mildly acidic conditions. The enamine can be reduced to the corresponding amine with NaBH4 via the nucleophilic addition of a hydride ion to the imine carbon.

Interpretation Introduction

(c)

Interpretation:

Steps to synthesize amine from a ketone or aldehyde is to be proposed

Concept introduction:

Aldehydes and ketones react with ammonia and primary amines to form an imine. The reaction occurs as a nucleophilic addition of the amine to the carbonyl carbon followed by protonation and elimination of H2O under mildly acidic conditions. The imine can be reduced to the corresponding amine with NaBH4 via nucleophilic addition of a hydride ion to the imine carbon.

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Answer 5

Chapter 18, Problem 18.41P

Interpretation Introduction

(a)

Interpretation:

How the given amine can be synthesized from a ketone or an aldehyde is to be shown.

Concept introduction:

Aldehydes and ketones react with ammonia and primary amines to form an imine. The reaction occurs as a nucleophilic addition of the amine to the carbonyl carbon followed by protonation and elimination of H2O under mildly acidic conditions. The imine can be reduced to the corresponding amine with NaBH4 via nucleophilic addition of a hydride ion to the imine carbon.

Interpretation Introduction

(b)

Interpretation:

How the given amine can be synthesized from a ketone or an aldehyde is to be shown.

Concept introduction:

Aldehydes and ketones react with secondary amines to form an enamine. Since there is only one hydrogen attached to the nitrogen atom, imine formation cannot occur. Instead, a proton from the α-carbon is extracted to form an enamine. The reaction occurs as a nucleophilic addition of the amine to the carbonyl carbon followed by protonation and elimination of H2O under mildly acidic conditions. The enamine can be reduced to the corresponding amine with NaBH4 via the nucleophilic addition of a hydride ion to the imine carbon.

Interpretation Introduction

(c)

Interpretation:

Steps to synthesize amine from a ketone or aldehyde is to be proposed

Concept introduction:

Aldehydes and ketones react with ammonia and primary amines to form an imine. The reaction occurs as a nucleophilic addition of the amine to the carbonyl carbon followed by protonation and elimination of H2O under mildly acidic conditions. The imine can be reduced to the corresponding amine with NaBH4 via nucleophilic addition of a hydride ion to the imine carbon.

Answer 6

Chapter 18, Problem 18.41P

Interpretation Introduction

(a)

Interpretation:

How the given amine can be synthesized from a ketone or an aldehyde is to be shown.

Concept introduction:

Aldehydes and ketones react with ammonia and primary amines to form an imine. The reaction occurs as a nucleophilic addition of the amine to the carbonyl carbon followed by protonation and elimination of H2O under mildly acidic conditions. The imine can be reduced to the corresponding amine with NaBH4 via nucleophilic addition of a hydride ion to the imine carbon.

Answer 7

Chapter 18, Problem 18.41P

Interpretation Introduction

(a)

Interpretation:

How the given amine can be synthesized from a ketone or an aldehyde is to be shown.

Concept introduction:

Aldehydes and ketones react with ammonia and primary amines to form an imine. The reaction occurs as a nucleophilic addition of the amine to the carbonyl carbon followed by protonation and elimination of H2O under mildly acidic conditions. The imine can be reduced to the corresponding amine with NaBH4 via nucleophilic addition of a hydride ion to the imine carbon.

Answer 8

Interpretation Introduction

(b)

Interpretation:

How the given amine can be synthesized from a ketone or an aldehyde is to be shown.

Concept introduction:

Aldehydes and ketones react with secondary amines to form an enamine. Since there is only one hydrogen attached to the nitrogen atom, imine formation cannot occur. Instead, a proton from the α-carbon is extracted to form an enamine. The reaction occurs as a nucleophilic addition of the amine to the carbonyl carbon followed by protonation and elimination of H2O under mildly acidic conditions. The enamine can be reduced to the corresponding amine with NaBH4 via the nucleophilic addition of a hydride ion to the imine carbon.

Answer 9

Interpretation Introduction

(b)

Interpretation:

How the given amine can be synthesized from a ketone or an aldehyde is to be shown.

Concept introduction:

Aldehydes and ketones react with secondary amines to form an enamine. Since there is only one hydrogen attached to the nitrogen atom, imine formation cannot occur. Instead, a proton from the α-carbon is extracted to form an enamine. The reaction occurs as a nucleophilic addition of the amine to the carbonyl carbon followed by protonation and elimination of H2O under mildly acidic conditions. The enamine can be reduced to the corresponding amine with NaBH4 via the nucleophilic addition of a hydride ion to the imine carbon.

Answer 10

Interpretation Introduction

(c)

Interpretation:

Steps to synthesize amine from a ketone or aldehyde is to be proposed

Concept introduction:

Aldehydes and ketones react with ammonia and primary amines to form an imine. The reaction occurs as a nucleophilic addition of the amine to the carbonyl carbon followed by protonation and elimination of H2O under mildly acidic conditions. The imine can be reduced to the corresponding amine with NaBH4 via nucleophilic addition of a hydride ion to the imine carbon.

Answer 11

Interpretation Introduction

(c)

Interpretation:

Steps to synthesize amine from a ketone or aldehyde is to be proposed

Concept introduction:

Aldehydes and ketones react with ammonia and primary amines to form an imine. The reaction occurs as a nucleophilic addition of the amine to the carbonyl carbon followed by protonation and elimination of H2O under mildly acidic conditions. The imine can be reduced to the corresponding amine with NaBH4 via nucleophilic addition of a hydride ion to the imine carbon.

Answer 12

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Answer 13

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Answer 14

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Answer 15

Ch. 18 - Prob. 18.1P Ch. 18 - Prob. 18.2P Ch. 18 - Prob. 18.3P Ch. 18 - Prob. 18.4P Ch. 18 - Prob. 18.5P Ch. 18 - Prob. 18.6P Ch. 18 - Prob. 18.7P Ch. 18 - Prob. 18.8P Ch. 18 - Prob. 18.9P Ch. 18 - Prob. 18.10P

Solution Summary: The author explains how the given amine can be synthesized from a ketone or an aldehyde.

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