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

Addition of Amine Derivatives

Organic Chemistry

21. Aldehydes and Ketones: Nucleophilic Addition

Addition of Amine Derivatives

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1:47 minutes

Problem 53a

Textbook Question

Predict the products formed when cyclohexanone reacts with the following reagents.
(a) CH₃NH₂, H⁺

Verified step by step guidance

Step 1: Recognize the type of reaction. Cyclohexanone is a ketone, and the reagents CH3NH2 (methylamine) and H+ indicate an imine formation reaction, also known as a Schiff base formation. This reaction involves the nucleophilic addition of the amine to the carbonyl group of the ketone, followed by dehydration.

Step 2: Identify the nucleophile and electrophile. The carbonyl carbon in cyclohexanone is electrophilic due to the partial positive charge, while the nitrogen in CH3NH2 is nucleophilic due to its lone pair of electrons.

Step 3: Describe the mechanism. The reaction begins with the nucleophilic attack of the amine (CH3NH2) on the carbonyl carbon of cyclohexanone. This forms a tetrahedral intermediate where the oxygen of the carbonyl group becomes negatively charged.

Step 4: Protonation and dehydration. Under acidic conditions (H+), the intermediate undergoes protonation of the hydroxyl group, followed by the elimination of water (dehydration). This results in the formation of a double bond between the carbon and nitrogen, yielding an imine (Schiff base).

Step 5: Predict the product. The final product is an imine where the nitrogen is bonded to the cyclohexane ring via a double bond and also to a methyl group (CH3). The structure can be represented as: \( \text{C}_6\text{H}_{10}=N-\text{CH}_3 \).

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Key Concepts

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

Nucleophilic Addition

Nucleophilic addition is a fundamental reaction mechanism in organic chemistry where a nucleophile attacks an electrophilic carbon atom, typically in a carbonyl group. In the case of cyclohexanone, the carbonyl carbon is susceptible to attack by nucleophiles like amines. This reaction leads to the formation of an intermediate that can further react to yield various products.

Amine Reactivity

Amines are organic compounds derived from ammonia, where one or more hydrogen atoms are replaced by alkyl or aryl groups. In the presence of an acid (H+), amines can act as nucleophiles, forming stable adducts with carbonyl compounds. The reaction of cyclohexanone with methylamine (CH3NH2) in acidic conditions typically results in the formation of an imine or an enamine, depending on the reaction conditions.

Protonation of Carbonyl Oxygen

Protonation of the carbonyl oxygen enhances the electrophilicity of the carbonyl carbon, making it more susceptible to nucleophilic attack. In acidic conditions, the carbonyl oxygen of cyclohexanone can be protonated, which stabilizes the carbonyl and facilitates the subsequent nucleophilic addition by the amine. This step is crucial for understanding the mechanism and predicting the products of the reaction.

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