Table of contents

1. A Review of General Chemistry5h 5m
2. Molecular Representations1h 14m
3. Acids and Bases2h 46m
4. Alkanes and Cycloalkanes4h 17m
5. Chirality3h 39m
6. Thermodynamics and Kinetics1h 22m
7. Substitution Reactions1h 48m
8. Elimination Reactions2h 30m
9. Alkenes and Alkynes2h 9m
10. Addition Reactions3h 19m
11. Radical Reactions1h 58m
12. Alcohols, Ethers, Epoxides and Thiols2h 42m
13. Alcohols and Carbonyl Compounds2h 17m
14. Synthetic Techniques1h 26m
15. Analytical Techniques:IR, NMR, Mass Spect7h 3m
16. Conjugated Systems6h 13m
17. Ultraviolet Spectroscopy51m
18. Aromaticity2h 34m
19. Reactions of Aromatics: EAS and Beyond5h 1m
20. Phenols55m
21. Aldehydes and Ketones: Nucleophilic Addition4h 56m
22. Carboxylic Acid Derivatives: NAS2h 51m
23. The Chemistry of Thioesters, Phophate Ester and Phosphate Anhydrides1h 10m
24. Enolate Chemistry: Reactions at the Alpha-Carbon1h 53m
25. Condensation Chemistry2h 9m
26. Amines1h 43m
27. Heterocycles2h 0m
28. Carbohydrates5h 53m
29. Amino Acids4h 20m
30. Peptides and Proteins2h 42m
31. Catalysis in Organic Reactions1h 30m
32. Lipids 2h 50m
33. The Organic Chemistry of Metabolic Pathways2h 52m
34. Nucleic Acids1h 32m
35. Transition Metals6h 14m
36. Synthetic Polymers1h 49m

21. Aldehydes and Ketones: Nucleophilic Addition

Imine vs Enamine

Organic Chemistry

21. Aldehydes and Ketones: Nucleophilic Addition

Imine vs Enamine

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4:48 minutes

Problem 8c

Textbook Question

Give the expected products of the following acid-catalyzed reactions.
(c) cyclohexanone + aniline

Verified step by step guidance

Step 1: Recognize that the reaction involves cyclohexanone (a ketone) and aniline (an amine) under acid-catalyzed conditions. This is a classic example of imine formation, where a ketone reacts with a primary amine to form an imine (Schiff base).

Step 2: Under acidic conditions, the carbonyl group of cyclohexanone is protonated, increasing the electrophilicity of the carbonyl carbon. This makes it more susceptible to nucleophilic attack by the lone pair on the nitrogen atom of aniline.

Step 3: The nucleophilic nitrogen of aniline attacks the electrophilic carbonyl carbon of cyclohexanone, forming a tetrahedral intermediate. This intermediate contains both the amine group and the hydroxyl group attached to the same carbon.

Step 4: The tetrahedral intermediate undergoes dehydration (loss of water) under acidic conditions. This step involves the protonation of the hydroxyl group, followed by its elimination as water, leading to the formation of a double bond between the carbon and nitrogen atoms.

Step 5: The final product is an imine, specifically N-phenylcyclohexanimine, where the nitrogen of aniline is double-bonded to the carbon of the former carbonyl group in cyclohexanone. This imine is stabilized under the reaction conditions.

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Key Concepts

Here are the essential concepts you must grasp in order to answer the question correctly.

Acid-Catalyzed Reactions

Acid-catalyzed reactions involve the use of an acid to increase the rate of a chemical reaction. In organic chemistry, acids can protonate reactants, making them more electrophilic and facilitating nucleophilic attacks. This is particularly important in reactions involving carbonyl compounds, such as ketones and aldehydes, where the carbonyl carbon becomes more reactive in the presence of an acid.

Nucleophilic Addition to Carbonyls

Nucleophilic addition to carbonyls is a fundamental reaction in organic chemistry where a nucleophile attacks the electrophilic carbon of a carbonyl group (C=O). In the case of cyclohexanone reacting with aniline, the nitrogen atom of aniline acts as a nucleophile, attacking the carbonyl carbon of cyclohexanone, leading to the formation of an intermediate that can further react to yield the final product.

Formation of Imines

The reaction between a carbonyl compound and a primary amine, such as aniline, typically leads to the formation of an imine. This process involves the nucleophilic attack of the amine on the carbonyl carbon, followed by the elimination of water. The resulting imine is characterized by a C=N double bond and is an important functional group in organic synthesis, often used in further transformations.

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