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

The mechanism for acidic hydrolysis of a nitrile resembles the basic hydrolysis, exceptthat the nitrile is first protonated, activating it toward attack by a weak nucleophile (water).Under acidic conditions, the proton transfer (tautomerism) involves protonation on nitrogen followed by deprotonation on oxygen. Propose a mechanism for the acid-catalyzedhydrolysis of benzonitrile to benzamide.

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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The mechanism for acidic hydrolysis of a nitrile resembles the basic hydrolysis, exceptthat the nitrile is first protonated, activating it toward attack by a weak nucleophile (water).Under acidic conditions, the proton transfer (tautomerism) involves protonation on nitrogen followed by deprotonation on oxygen. Propose a mechanism for the acid-catalyzedhydrolysis of benzonitrile to benzamide.

Benzene + nitration, followed by bromination, then reduction of the nitro group to an amine, followed by diazonization, addition of copper I cyanide to the reaction and the product is O benzoyl nitrile O ortho-bromoaniline O para-bromo-nitrobenzene O 3,5-dibromnobenzonitrile O para-bromobenzyl bromide

Treating trimethylamine with 2-chloroethyl acetate gives acetylcholine as its chloride. Acetylcholine is a neurotransmitter. Me;N + CH,COCH,CH,CI C,H1,CINO, Acetylcholine chloride Propose a structural formula for this quaternary ammonium salt and a mechanism for its formation.

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

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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