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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5:14 minutes

Problem 23a,b,c

Textbook Question

Show what amines and carbonyl compounds combine to give the following derivatives.
(a)
(b)
(c)

Verified step by step guidance

Step 1: Analyze the given derivatives in the images. Each derivative is formed by the reaction of an amine with a carbonyl compound. Identify the functional groups present in each derivative to deduce the starting materials.

Step 2: For derivative (a), observe the structure. It contains a hydrazone functional group (-C=N-NH2). This suggests that the derivative is formed by the reaction of a hydrazine (H2N-NH2) with an aldehyde or ketone. The carbonyl compound here is likely an aldehyde due to the presence of a hydrogen atom attached to the carbonyl carbon.

Step 3: For derivative (b), observe the structure. It contains an oxime functional group (-C=N-OH). Oximes are formed by the reaction of hydroxylamine (NH2OH) with a carbonyl compound. The cyclic structure indicates that the carbonyl compound is a cyclohexanone.

Step 4: For derivative (c), observe the structure. It contains a Schiff base functional group (-C=N-NHPh). Schiff bases are formed by the reaction of a primary amine (in this case, aniline, NH2Ph) with a carbonyl compound. The cyclic structure indicates that the carbonyl compound is likely cyclopentanone.

Step 5: Summarize the reactions: (a) Hydrazine reacts with an aldehyde to form the hydrazone derivative. (b) Hydroxylamine reacts with cyclohexanone to form the oxime derivative. (c) Aniline reacts with cyclopentanone to form the Schiff base derivative.

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Key Concepts

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

Amines

Amines are organic compounds derived from ammonia (NH3) by replacing one or more hydrogen atoms with alkyl or aryl groups. They can be classified as primary, secondary, or tertiary based on the number of carbon-containing groups attached to the nitrogen atom. Amines are nucleophilic and can react with carbonyl compounds to form imines or enamines, depending on the reaction conditions.

Carbonyl Compounds

Carbonyl compounds contain a carbon atom double-bonded to an oxygen atom (C=O). This functional group is characteristic of aldehydes and ketones, which are key reactants in organic synthesis. The electrophilic nature of the carbonyl carbon allows it to react with nucleophiles, such as amines, leading to the formation of derivatives like imines and enamines through condensation reactions.

Imines and Enamines

Imines and enamines are derivatives formed from the reaction of amines with carbonyl compounds. Imines are formed when a primary amine reacts with a carbonyl compound, resulting in a C=N bond. Enamines, on the other hand, are formed from secondary amines and feature a C=C bond adjacent to a nitrogen atom. Both structures are important in organic synthesis and can serve as intermediates in various chemical reactions.

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