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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4:09 minutes

Problem 22a,b

Textbook Question

Predict the products of the following reactions.
(a)
(b)

Verified step by step guidance

Step 1: Analyze the reactants and reaction conditions for both parts (a) and (b). In (a), the reactants are cyclohexanone and hydroxylamine (NH2OH) under acidic conditions (H+). In (b), the reactants are bicyclo[2.2.1]heptan-2-one and hydrazine (NH2NH2) under acidic conditions (H+).

Step 2: Recognize the type of reaction occurring. In (a), hydroxylamine reacts with a ketone to form an oxime. This is a condensation reaction where the oxygen of the ketone is replaced by the nitrogen of hydroxylamine. In (b), hydrazine reacts with a ketone to form a hydrazone, which is also a condensation reaction.

Step 3: For (a), the mechanism involves nucleophilic attack by the nitrogen of hydroxylamine on the carbonyl carbon of cyclohexanone, followed by proton transfers and elimination of water to form the oxime. The product will have the structure R-C=N-OH, where R is the cyclohexane ring.

Step 4: For (b), the mechanism involves nucleophilic attack by the nitrogen of hydrazine on the carbonyl carbon of bicyclo[2.2.1]heptan-2-one, followed by proton transfers and elimination of water to form the hydrazone. The product will have the structure R-C=N-NH2, where R is the bicyclo[2.2.1]heptane ring.

Step 5: Verify the stereochemistry and connectivity of the products. Since both reactions involve planar carbonyl groups, the stereochemistry of the products will depend on the orientation of the reactants during the reaction. Ensure the final products are correctly drawn with the appropriate functional groups (oxime for (a) and hydrazone for (b)).

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Key Concepts

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

Imine and Enamine Formation

Imine and enamine formation are key reactions in organic chemistry involving the condensation of carbonyl compounds with amines. An imine is formed when a primary amine reacts with a carbonyl compound, resulting in the loss of water. In contrast, enamines are formed from secondary amines and involve a similar condensation process, but with a double bond between the nitrogen and the adjacent carbon.

Acid-Catalyzed Reactions

Acid-catalyzed reactions are chemical processes that require an acid to facilitate the reaction. In the context of imine and enamine formation, the presence of an acid (H+) helps protonate the carbonyl oxygen, increasing the electrophilicity of the carbonyl carbon, making it more susceptible to nucleophilic attack by the amine. This step is crucial for the successful formation of the desired products.

Nucleophilic Addition

Nucleophilic addition is a fundamental reaction mechanism in organic chemistry where a nucleophile attacks an electrophilic center, typically a carbonyl carbon. In the reactions presented, the amine acts as the nucleophile, attacking the electrophilic carbon of the carbonyl group. This step is essential for forming the intermediate that ultimately leads to the production of imines or enamines.

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