The structures of the amine and dialdehyde that react with dimethylacetonedicarboxylate in a Mannich reaction to yield cocaine are to be given. Concept introduction: The first step in a Mannich reaction involves a reaction between an aldehyde and a secondary amine, to yield an iminium ion intermediate along with water. In the second step the iminium ion intermediate reacts with cyclohexanone to yield the product. To give: The structures of the amine and dialdehyde that react with dimethylacetonedicarboxylate in a Mannich reaction to yield cocaine.

Question

An amine of unknown structure contains one nitrogen and nine carbon atoms. The 13C-NMR spectrum shows only five signals, all between 20 and 60 ppm. Three cycles of Hofmann elimination sequence [(1) CH3I; (2) Ag2O, H3O; (3) heat] give trimethylamine and 1,4,8-nonatriene. Propose a structural formula for the amine.

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 46MP

Interpretation Introduction

Interpretation:

The structures of the amine and dialdehyde that react with dimethylacetonedicarboxylate in a Mannich reaction to yield cocaine are to be given.

Concept introduction:

The first step in a Mannich reaction involves a reaction between an aldehyde and a secondary amine, to yield an iminium ion intermediate along with water. In the second step the iminium ion intermediate reacts with cyclohexanone to yield the product.

To give:

The structures of the amine and dialdehyde that react with dimethylacetonedicarboxylate in a Mannich reaction to yield cocaine.

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An amine of unknown structure contains one nitrogen and nine carbon atoms. The 13C-NMR spectrum shows only five signals, all between 20 and 60 ppm. Three cycles of Hofmann elimination sequence [(1) CH3I; (2) Ag2O, H3O; (3) heat] give trimethylamine and 1,4,8-nonatriene. Propose a structural formula for the amine.

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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 23.SE, Problem 46MP

Interpretation Introduction

Interpretation:

The structures of the amine and dialdehyde that react with dimethylacetonedicarboxylate in a Mannich reaction to yield cocaine are to be given.

Concept introduction:

The first step in a Mannich reaction involves a reaction between an aldehyde and a secondary amine, to yield an iminium ion intermediate along with water. In the second step the iminium ion intermediate reacts with cyclohexanone to yield the product.

To give:

The structures of the amine and dialdehyde that react with dimethylacetonedicarboxylate in a Mannich reaction to yield cocaine.

Expert Solution & Answer

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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 46MP

Interpretation Introduction

Interpretation:

The structures of the amine and dialdehyde that react with dimethylacetonedicarboxylate in a Mannich reaction to yield cocaine are to be given.

Concept introduction:

The first step in a Mannich reaction involves a reaction between an aldehyde and a secondary amine, to yield an iminium ion intermediate along with water. In the second step the iminium ion intermediate reacts with cyclohexanone to yield the product.

To give:

The structures of the amine and dialdehyde that react with dimethylacetonedicarboxylate in a Mannich reaction to yield cocaine.

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 46MP

Interpretation Introduction