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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2:14 minutes

Problem 39i

Textbook Question

Predict the major products of the following reactions.
(i)

Verified step by step guidance

Step 1: Identify the functional groups in the reactants. The starting compound is cyclohexanone, which contains a ketone functional group (C=O). The reagent is aniline (PhNH2), which contains an amine group (-NH2) attached to a phenyl ring.

Step 2: Recognize the type of reaction. This is a nucleophilic addition reaction where the amine group of aniline will react with the carbonyl group of cyclohexanone. The reaction typically forms an imine (Schiff base) as the major product.

Step 3: Understand the mechanism. The lone pair of electrons on the nitrogen atom of aniline will attack the electrophilic carbon of the carbonyl group in cyclohexanone. This forms a tetrahedral intermediate.

Step 4: Eliminate water. After the intermediate forms, a dehydration step occurs, where a molecule of water is eliminated to form the imine product. The final product will have a C=N bond with the phenyl group attached to the nitrogen.

Step 5: Verify the structure of the product. The major product will be N-phenylcyclohexylimine, which has the structure: cyclohexane ring with a double bond to nitrogen, and the nitrogen bonded to a phenyl group.

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Key Concepts

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

Imine Formation

Imine formation is a reaction between a carbonyl compound (like an aldehyde or ketone) and an amine, resulting in the creation of an imine. This process involves the nucleophilic attack of the amine on the carbonyl carbon, followed by the elimination of water. Understanding this mechanism is crucial for predicting the products of reactions involving carbonyls and amines.

Nucleophilic Addition

Nucleophilic addition is a fundamental reaction in organic chemistry where a nucleophile attacks an electrophilic center, typically a carbon atom in a carbonyl group. This reaction is essential for understanding how various functional groups interact, particularly in the context of carbonyl compounds reacting with nucleophiles like amines. The outcome of this reaction often leads to the formation of new functional groups.

Reaction Conditions

The conditions under which a reaction occurs can significantly influence the products formed. Factors such as temperature, solvent, and the presence of catalysts can affect the rate and outcome of the reaction. In the case of imine formation, understanding the reaction environment helps predict whether the reaction will proceed to completion and the stability of the resulting imine product.

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