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

Methamphetamine is a long-lasting, potent stimulant sold as a street drug. The synthesis is quite simple and one step in the synthesis is shown below. Using your knowledge of the reactions of amines, provide all the reagents necessary to complete the reaction below. Provide the reagents for step 1 and step 2 ,

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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Methamphetamine is a long-lasting, potent stimulant sold as a street drug. The synthesis is quite simple and one step in the synthesis is shown below. Using your knowledge of the reactions of amines, provide all the reagents necessary to complete the reaction below. Provide the reagents for step 1 and step 2 ,

The following three derivatives of succinimide are anticonvulsants that have found use in the treatment of epilepsy, particularly petit mal seizures. Q. Of these three anticonvulsants, one is considerably more acidic than the other two. Which is the most acidic compound? Estimate its pKa and account for its acidity. How does its acidity compare with that of phenol? with that of acetic acid?

Ibufenac, a para-disubstituted arene with the structureHO2CCH2C6H4CH2CH(CH3)2 , is a much more potent analgesic thanaspirin, but it was never sold commercially because it caused livertoxicity in some clinical trials. Devise a synthesis of ibufenac frombenzene and organic halides having fewer than five carbons.

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

Trending nowThis is a popular solution!

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