A mechanism for the first step in the Mannich reaction shown, a reaction between acetaldehyde and dimethyl amine , to yield an iminium ion intermediate along with water is to be proposed. The structure of the iminium ion intermediate is to be given. Further the mechanism of the second step involving the reaction between iminium ion intermediate and cyclohexanone is also to be proposed. Concept introduction: The steps involved in the formation of the iminium ion are i) Protonation of the aldehyde ii) Nucleophilic attack of the amine on the protonated aldehyde iii) A proton exchange iv) Loss of water to yield the iminium ion. The reaction between iminium ion intermediate and cyclohexanone takes place through the following steps i) Reaction between the enol form of the cyclohexanone and iminium ion ii) Deprotonation of the intermediate. To propose: A mechanism for the first step in the Mannich reaction shown, a reaction between acetaldehyde and dimethyl amine, to yield an iminium ion intermediate along with water. To show the structure of the iminium ion intermediate. Further to propose a mechanism for the second step involving the reaction between iminium ion intermediate and cyclohexanone.

Question

11 1 Which one of the following compounds would show a proton NMR signal at the highest chemical shift? (7pts) cl @amitabh CI CI d) Cl CICI

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 23.SE, Problem 45MP

Interpretation Introduction

Interpretation:

A mechanism for the first step in the Mannich reaction shown, a reaction between acetaldehyde and dimethyl amine, to yield an iminium ion intermediate along with water is to be proposed. The structure of the iminium ion intermediate is to be given. Further the mechanism of the second step involving the reaction between iminium ion intermediate and cyclohexanone is also to be proposed.

Concept introduction:

The steps involved in the formation of the iminium ion are i) Protonation of the aldehyde ii) Nucleophilic attack of the amine on the protonated aldehyde iii) A proton exchange iv) Loss of water to yield the iminium ion.

The reaction between iminium ion intermediate and cyclohexanone takes place through the following steps i) Reaction between the enol form of the cyclohexanone and iminium ion ii) Deprotonation of the intermediate.

To propose:

A mechanism for the first step in the Mannich reaction shown, a reaction between acetaldehyde and dimethyl amine, to yield an iminium ion intermediate along with water. To show the structure of the iminium ion intermediate.

Further to propose a mechanism for the second step involving the reaction between iminium ion intermediate and cyclohexanone.

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11 1 Which one of the following compounds would show a proton NMR signal at the highest chemical shift? (7pts) cl @amitabh CI CI d) Cl CICI

None

H2SO4 (cat.), H₂O 100 °C NH₂

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 23.SE, Problem 45MP

Interpretation Introduction

Interpretation:

A mechanism for the first step in the Mannich reaction shown, a reaction between acetaldehyde and dimethyl amine, to yield an iminium ion intermediate along with water is to be proposed. The structure of the iminium ion intermediate is to be given. Further the mechanism of the second step involving the reaction between iminium ion intermediate and cyclohexanone is also to be proposed.

Concept introduction:

The steps involved in the formation of the iminium ion are i) Protonation of the aldehyde ii) Nucleophilic attack of the amine on the protonated aldehyde iii) A proton exchange iv) Loss of water to yield the iminium ion.

The reaction between iminium ion intermediate and cyclohexanone takes place through the following steps i) Reaction between the enol form of the cyclohexanone and iminium ion ii) Deprotonation of the intermediate.

To propose:

A mechanism for the first step in the Mannich reaction shown, a reaction between acetaldehyde and dimethyl amine, to yield an iminium ion intermediate along with water. To show the structure of the iminium ion intermediate.

Further to propose a mechanism for the second step involving the reaction between iminium ion intermediate and cyclohexanone.

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Check out sample textbook solution

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 23.SE, Problem 45MP

Interpretation Introduction

Interpretation:

A mechanism for the first step in the Mannich reaction shown, a reaction between acetaldehyde and dimethyl amine, to yield an iminium ion intermediate along with water is to be proposed. The structure of the iminium ion intermediate is to be given. Further the mechanism of the second step involving the reaction between iminium ion intermediate and cyclohexanone is also to be proposed.

Concept introduction:

The steps involved in the formation of the iminium ion are i) Protonation of the aldehyde ii) Nucleophilic attack of the amine on the protonated aldehyde iii) A proton exchange iv) Loss of water to yield the iminium ion.

The reaction between iminium ion intermediate and cyclohexanone takes place through the following steps i) Reaction between the enol form of the cyclohexanone and iminium ion ii) Deprotonation of the intermediate.

To propose:

A mechanism for the first step in the Mannich reaction shown, a reaction between acetaldehyde and dimethyl amine, to yield an iminium ion intermediate along with water. To show the structure of the iminium ion intermediate.

Further to propose a mechanism for the second step involving the reaction between iminium ion intermediate and cyclohexanone.

Expert Solution & Answer

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See solution

Check out sample textbook solution

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 23.SE, Problem 45MP

Interpretation Introduction