Imine and Enamine are nitrogenous compounds. The primary difference between imine and enamine is that imine consists of a C=N double bond while enamine consists of a C-N single bond. Imine has a C=N functional group. In contrast, enamine has an amine group adjacent to the C=C double bond.
This section will discuss Imine, Enamine, Synthesis of Imine and Enamine, Differences between Imine and Enamine in detail.
Table of Content
- What is an Imine?
- What is an Enamine?
- Synthesis of Imine
- Synthesis of Enamine
- Differences between Imine and Enamine
- Frequently Asked Questions – FAQs
What is an Imine?
An imine is an organic compound consisting of a C=N double bond. If the nitrogen atom is bonded with an alkyl group, the imine is called Schiffs Base. The first imine compound was discovered by a German chemist Albert Ladenburg.
The imine is often related to aldehydes and ketones by replacing oxygen with an NR group.
- When an RH group replaces the oxygen atom, the imine is primary.
- When R is hydrocarbyl, the imine is secondary.
What is an Enamine?
The word enamine is derived from the suffix en of alkene and the root amine. An enamine is an unsaturated organic compound with an amine group adjacent to the C=C double bond. It is also considered as nitrogen analogues of enols. They are derived by condensing an aldehyde or ketone with a secondary amine.
- Enamine acts as a good base as well as a nucleophile.
Synthesis of Imine
Reaction with Primary Amines
Imine and its by-products are synthesised by reacting ammonia or primary amine with aldehyde or ketone. It is a condensation reaction as water is eliminated during imine formation. The carbonyl oxygen is removed from aldehyde or ketone, and nitrogen substitutes carbonyl oxygen to form a C=N bond.
Synthesis of Enamine
Reaction with Primary Amines
Enamine and its by-products are synthesised by reacting a secondary amine with aldehyde or ketone. The carbonyl oxygen is removed from aldehyde or ketone, and nitrogen substitutes carbonyl oxygen to form a C-N bond. It is a condensation reaction as water is eliminated during enamine formation.
Difference between Imine and Enamine
| S No. | Imine | Enamine |
|---|---|---|
| 1. | An imine is an organic compound consisting of a C=N double bond. | An enamine is an unsaturated organic compound with an amine group adjacent to the C=C double bond. |
| 2. | There is a pi bond between carbon and nitrogen. | There is no pi bond between carbon and nitrogen, but there is unsaturation between adjacent carbon and carbon. |
| 3. | The general formula of imine is R2C=NR, where R is a hydrogen atom or an organic substituent. | The general formula of imine is R2C=CR(NR2), where R is a hydrogen atom or an organic substituent. |
| 4. | Imine and its by-products are synthesised by reacting ammonia or primary amine with aldehyde or ketone. | Enamine and its by-products are synthesised by reacting a secondary amine with aldehyde or ketone. |
| 5. | Imine is more stable than enamine. | Enamine is less stable than imine. |
Frequently Asked Questions on Imine vs Enamine
What is an Imine?
An imine is an organic compound consisting of a C=N double bond. The imine is often related to aldehydes and ketones by replacing oxygen with an NR group. If the nitrogen atom is bonded with an alkyl group, the imine is called Schiffs Base.
What is an Enamine?
An enamine is an unsaturated organic compound with an amine group adjacent to the C=C double bond. It is also considered as nitrogen analogues of enols. They are derived by condensing an aldehyde or ketone with a secondary amine.
Is imine electrophilic or nucleophilic?
Imine was found to be slightly electrophilic. In contrast, enamine is a good nucleophile.
Are imine and enamine same?
No, imine and enamine are not same. The primary difference between imine and enamine is that imine consists of a C=N double bond while enamine consists of a C-N single bond. Imine has a C=N functional group. In contrast, enamine has an amine group adjacent to the C=C double bond.
How can you synthesise enamine?
Enamine and its by-products are synthesised by reacting a secondary amine with aldehyde or ketone. The carbonyl oxygen is removed from aldehyde or ketone, and nitrogen substitutes carbonyl oxygen to form a C-N bond. It is a condensation reaction as water is eliminated during enamine formation.
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