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

Previous problemNext problem

4:41 minutes

Problem 39g

Textbook Question

Predict the products of the following reactions:
(g)

Verified step by step guidance

Step 1: Identify the functional group in the starting material. In this case, the starting material is a cyclic ketone (cyclohexanone). The carbonyl group (C=O) is reactive and will undergo nucleophilic attack.

Step 2: Recognize the reagents provided. The reaction involves ethylamine (EtNH₂) in the presence of an acid catalyst (H⁺). This suggests an imine formation reaction, where the amine reacts with the ketone to form an imine, with water (H₂O) as a byproduct.

Step 3: Understand the mechanism. The reaction proceeds as follows: (a) Protonation of the carbonyl oxygen by H⁺ increases the electrophilicity of the carbonyl carbon. (b) Ethylamine (EtNH₂) acts as a nucleophile and attacks the carbonyl carbon, forming a tetrahedral intermediate. (c) The intermediate undergoes dehydration (-H₂O) to form the imine product.

Step 4: Predict the structure of the product. The imine product will have the ethyl group (CH₃CH₂-) attached to the nitrogen atom, and the double bond will form between the nitrogen and the carbon that was originally part of the carbonyl group.

Step 5: Verify the reaction conditions. Ensure that the reaction is carried out under acidic conditions to facilitate protonation and dehydration, which are essential for imine formation.

Verified video answer for a similar problem:

This video solution was recommended by our tutors as helpful for the problem above

Video duration:

Play a video:

Was this helpful?

Key Concepts

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

Electrophilic Addition

Electrophilic addition is a fundamental reaction mechanism in organic chemistry where an electrophile reacts with a nucleophile, leading to the formation of a more complex molecule. In this context, the carbonyl group (C=O) acts as an electrophile, attracting nucleophiles such as amines. Understanding this mechanism is crucial for predicting the products of reactions involving carbonyl compounds.

Amine Nucleophiles

Amines are organic compounds derived from ammonia by replacing one or more hydrogen atoms with alkyl or aryl groups. In the given reaction, ethylamine (EtNH2) serves as a nucleophile that attacks the electrophilic carbon of the carbonyl group. Recognizing the role of amines in nucleophilic addition reactions is essential for predicting the resulting products, particularly in the formation of imines or enamines.

Dehydration Reactions

Dehydration reactions involve the removal of water (H2O) from a molecule, often leading to the formation of double bonds or new functional groups. In this case, after the nucleophilic attack by ethylamine on the carbonyl compound, the subsequent loss of water results in the formation of an imine. Understanding dehydration is key to predicting the final product of the reaction, especially in the context of carbonyl chemistry.

Watch next

Master General Reactions with a bite sized video explanation from Johnny

Start learning