N-ethylideneethylamine

Definition

N-ethylideneethylamine is a type of imine, which is a functional group formed by the condensation reaction between a primary amine and an aldehyde or ketone. It consists of a carbon-nitrogen double bond with an ethyl group attached to the nitrogen atom and an ethylidene group attached to the carbon atom.

5 Must Know Facts For Your Next Test

1. N-ethylideneethylamine is formed through the nucleophilic addition of a primary amine to an aldehyde or ketone, resulting in the elimination of water.
2. The formation of N-ethylideneethylamine is an example of imine formation, a key step in many organic reactions.
3. Imines can undergo further reactions, such as reduction to form secondary amines or hydrolysis to regenerate the original amine and carbonyl compounds.
4. The presence of the ethylidene group in N-ethylideneethylamine allows for the potential formation of an enamine, which can participate in additional nucleophilic addition reactions.
5. Imines and enamines are important intermediates in various organic transformations, including the synthesis of heterocyclic compounds and the Diels-Alder reaction.

Review Questions

• Describe the mechanism for the formation of N-ethylideneethylamine from a primary amine and an aldehyde or ketone.
  • The formation of N-ethylideneethylamine involves a nucleophilic addition reaction between a primary amine and an aldehyde or ketone. The amine first attacks the carbonyl carbon, forming a tetrahedral intermediate. This is followed by the elimination of water, resulting in the formation of the planar imine bond. The presence of the ethyl group on the nitrogen and the ethylidene group on the carbon gives N-ethylideneethylamine its specific structure.
• Explain how the formation of N-ethylideneethylamine is related to the topics of imine and enamine formation.
  • N-ethylideneethylamine is a specific example of an imine, which is a class of compounds formed by the condensation of a primary amine and a carbonyl compound. The formation of N-ethylideneethylamine is a key step in imine formation reactions. Additionally, the presence of the ethylidene group in N-ethylideneethylamine allows for the potential formation of an enamine, where the imine is conjugated with a carbon-carbon double bond. Enamines can then participate in further nucleophilic addition reactions, making them important intermediates in organic synthesis.
• Discuss the significance of N-ethylideneethylamine and its role in the broader context of nucleophilic addition reactions involving amines.
  • N-ethylideneethylamine is a representative example of the nucleophilic addition of amines to carbonyl compounds, a fundamental reaction in organic chemistry. The formation of this imine intermediate is crucial, as it can undergo further transformations, such as reduction to secondary amines or hydrolysis to regenerate the original amine and carbonyl compounds. Additionally, the potential for N-ethylideneethylamine to form an enamine expands the synthetic utility of this reaction, as enamines can participate in a variety of nucleophilic addition and pericyclic reactions. Understanding the formation and reactivity of N-ethylideneethylamine is therefore essential for comprehending the broader scope of nucleophilic addition reactions involving amines.

Related terms

Imine:

An imine is a functional group that consists of a carbon-nitrogen double bond, where the nitrogen atom is connected to an alkyl or aryl group.

Enamine:

An enamine is a type of imine where the carbon-nitrogen double bond is conjugated with a carbon-carbon double bond, forming an extended pi-system.

Nucleophilic Addition:

Nucleophilic addition is a type of reaction where a nucleophile (a species with a high electron density) attacks the carbon of a carbonyl group, leading to the formation of a new bond.