- Aa Schiff’s base
- Ban enamine
- Can imine
- Dan amine
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Correct answer: B
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Identify the reactants
- Carbonyl compound: cyclohexanone (a ketone)
- Amine: dimethylamine, which is a secondary amine
- Conditions: catalytic acid and continuous removal of water
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Recall the general reaction of carbonyl compounds with amines
Carbonyl compounds react with amines by nucleophilic addition followed by dehydration.
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With a primary amine, the product is an imine (also called Schiff base in many cases):
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With a secondary amine, the product is generally an enamine:
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Why not imine/Schiff base here?
Dimethylamine is , a secondary amine. Formation of an imine requires a nitrogen atom that still has one hydrogen initially and can end up double-bonded to carbon after loss of water. Secondary amines instead give an intermediate iminium ion, followed by loss of an -hydrogen to form an enamine.
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Role of removing water
Since the reaction is reversible, continuous removal of water drives the equilibrium toward the condensation product by Le Chatelier’s principle.
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Conclusion
Therefore, cyclohexanone reacts with dimethylamine under acidic conditions to form an enamine.
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Option check
- A: Schiff’s base formed typically with primary amines, not secondary amines
- B: enamine correct
- C: imine not with a secondary amine
- D: amine incorrect
Hence, the correct answer is B.
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