What is the Difference Between Imine and Enamine?
🆚 Go to Comparative Table 🆚Imine and enamine are nitrogenous compounds with distinct characteristics. The primary difference between them is the type of bond they form:
- Imine: Consists of a C=N double bond. It has a C=N functional group and is derived by condensing an aldehyde or ketone with a secondary amine. Imines are considered electrophilic.
- Enamine: An unsaturated organic compound with an amine group adjacent to the C=C double bond. Enamines have a C-N single bond and are considered nucleophilic.
Some other differences between imines and enamines include:
- Imines have a pi bond between carbon and nitrogen, while enamines do not have a pi bond between carbon and nitrogen but have unsaturation between adjacent carbon atoms.
- Enamines are nitrogen analogues of enols, and they are formed through the addition of a secondary amine to an enolizable aldehyde or ketone in the presence of mild acid.
- Enamines are often used as intermediates in various synthetic reactions, such as alkylation, Michael addition, and hydrolysis with aqueous acid.
Comparative Table: Imine vs Enamine
Imines and enamines are both nitrogenous compounds, but they have different structures and properties. Here is a table summarizing the differences between them:
Property | Imines | Enamines |
---|---|---|
General Formula | R2C=NR | RNHC=CHR |
Structure | Consists of a C=N double bond | Has an amine group adjacent to the C=C double bond |
Formation | Imines are formed by the reaction of an aldehyde or ketone with a primary amine | Enamines are formed by the reaction of an aldehyde or ketone with a secondary amine |
Reactivity | Imines are slightly electrophilic | Enamines are good nucleophiles |
Reversibility | Imines can be hydrolyzed back to the corresponding primary amine under acidic conditions | Enamines can be dehydrated to form the corresponding aldehyde or ketone under acidic conditions |
In summary, imines have a C=N double bond and are formed by the reaction of an aldehyde or ketone with a primary amine, while enamines have an amine group adjacent to the C=C double bond and are formed by the reaction of an aldehyde or ketone with a secondary amine. Imines are slightly electrophilic, whereas enamines are good nucleophiles.
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