(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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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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2. Predict the NMR spectra for each of these two compounds by listing, in the NMR tables below, the chemical shift, the splitting, and the number of hydrogens associated with each predicted peak. Sort the peaks from largest chemical shift to lowest. **Not all slots must be filled** Peak Chemical Shift (d) 5.7 1 Multiplicity multiplate .......... 5.04 double of doublet 2 4.98 double of doublet 3 4.05 doublet of quartet 4 5 LO 3.80 quartet 1.3 doublet 6 Peak Chemical Shift (d) Multiplicity

Interpreting NMR spectra is a skill that often requires some amount of practice, which, in turn, necessitates access to a collection of NMR spectra. Beyond Labz Organic Synthesis and Organic Qualitative Analysis have spectral libraries containing over 700 1H NMR spectra. In this assignment, you will take advantage of this by first predicting the NMR spectra for two closely related compounds and then checking your predictions by looking up the actual spectra in the spectra library. After completing this assignment, you may wish to select other compounds for additional practice. 1. Write the IUPAC names for the following two structures: Question 2 Question 3 2. Predict the NMR spectra for each of these two compounds by listing, in the NMR tables below, the chemical shift, the splitting, and the number of hydrogens associated with each predicted peak. Sort the peaks from largest chemical shift to lowest. **Not all slots must be filled**

11:14 ... worksheets.beyondlabz.com 3. To check your predictions, click this link for Interpreting NMR Spectra 1. You will see a list of all the - compounds in the spectra library in alphabetical order by IUPAC name. Hovering over a name in the list will show the structure on the chalkboard. The four buttons on the top of the Spectra tab in the tray are used to select the different spectroscopic techniques for the selected compound. Make sure the NMR button has been selected. 4. Scroll through the list of names to find the names for the two compounds you have been given and click on the name to display the NMR spectrum for each. In the NMR tables below, list the chemical shift, the splitting, and the number of hydrogens associated with each peak for each compound. Compare your answers to your predictions. **Not all slots must be filled** Peak Chemical Shift (d) Multiplicity 1 2 3 4 5

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 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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