Glutamate is converted into α- ketoglutarate by the reaction sequence shown below. The structure of the imine intermediate is to be shown and mechanisms for both steps are to be proposed. Concept introduction: Transfer of a hydride ion from the glutamate to NAD+ followed by the deprotonation of the intermediate formed will yield the imine. The attack of water on the protonated imine and subsequent deprotonation yield a carbinolamine intermediate. The intermediate on further reaction breaks to yield a ketone and amine /ammonia as products. To show: The structure of the imine intermediate formed when glutamate is converted into α- ketoglutarate by the reaction sequence shown below and to propose mechanisms for both steps.

Question

ΗΝ, Draw Final Product C cyclohexanone pH 4-5 Edit Enamine H3O+ CH3CH2Br THF, reflux H Edit Iminium Ion

Answer 1

Question

Definition Definition Organic compounds that have a carbonyl group, C = O, as their functional group. The carbonyl group in ketones is placed somewhere in the middle of the molecular structure, which means, the C=O is attached to two alkyl groups or benzene rings. Just like all other homologous series, the naming of ketones is done using a common suffix “-one”. The general molecular formula is C n H 2n O. Functional group of a ketone

Chapter 19.SE, Problem 50MP

Interpretation Introduction

Interpretation:

Glutamate is converted into α- ketoglutarate by the reaction sequence shown below.

The structure of the imine intermediate is to be shown and mechanisms for both steps are to be proposed.

Concept introduction:

Transfer of a hydride ion from the glutamate to NAD+ followed by the deprotonation of the intermediate formed will yield the imine.

The attack of water on the protonated imine and subsequent deprotonation yield a carbinolamine intermediate. The intermediate on further reaction breaks to yield a ketone and amine/ammonia as products.

To show:

The structure of the imine intermediate formed when glutamate is converted into α- ketoglutarate by the reaction sequence shown below and to propose mechanisms for both steps.

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ΗΝ, Draw Final Product C cyclohexanone pH 4-5 Edit Enamine H3O+ CH3CH2Br THF, reflux H Edit Iminium Ion

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Answer 2

Question

Definition Definition Organic compounds that have a carbonyl group, C = O, as their functional group. The carbonyl group in ketones is placed somewhere in the middle of the molecular structure, which means, the C=O is attached to two alkyl groups or benzene rings. Just like all other homologous series, the naming of ketones is done using a common suffix “-one”. The general molecular formula is C n H 2n O. Functional group of a ketone

Chapter 19.SE, Problem 50MP

Interpretation Introduction

Interpretation:

Glutamate is converted into α- ketoglutarate by the reaction sequence shown below.

The structure of the imine intermediate is to be shown and mechanisms for both steps are to be proposed.

Concept introduction:

Transfer of a hydride ion from the glutamate to NAD+ followed by the deprotonation of the intermediate formed will yield the imine.

The attack of water on the protonated imine and subsequent deprotonation yield a carbinolamine intermediate. The intermediate on further reaction breaks to yield a ketone and amine/ammonia as products.

To show:

The structure of the imine intermediate formed when glutamate is converted into α- ketoglutarate by the reaction sequence shown below and to propose mechanisms for both steps.

Expert Solution & Answer

Trending nowThis is a popular solution!

See solution

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 ketones is placed somewhere in the middle of the molecular structure, which means, the C=O is attached to two alkyl groups or benzene rings. Just like all other homologous series, the naming of ketones is done using a common suffix “-one”. The general molecular formula is C n H 2n O. Functional group of a ketone

Chapter 19.SE, Problem 50MP

Interpretation Introduction

Interpretation:

Glutamate is converted into α- ketoglutarate by the reaction sequence shown below.

The structure of the imine intermediate is to be shown and mechanisms for both steps are to be proposed.

Concept introduction:

Transfer of a hydride ion from the glutamate to NAD+ followed by the deprotonation of the intermediate formed will yield the imine.

The attack of water on the protonated imine and subsequent deprotonation yield a carbinolamine intermediate. The intermediate on further reaction breaks to yield a ketone and amine/ammonia as products.

To show:

The structure of the imine intermediate formed when glutamate is converted into α- ketoglutarate by the reaction sequence shown below and to propose mechanisms for both steps.

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 ketones is placed somewhere in the middle of the molecular structure, which means, the C=O is attached to two alkyl groups or benzene rings. Just like all other homologous series, the naming of ketones is done using a common suffix “-one”. The general molecular formula is C n H 2n O. Functional group of a ketone

Chapter 19.SE, Problem 50MP

Interpretation Introduction