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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5:51 minutes

Problem 19d,e,f

Textbook Question

Give the structures of the carbonyl compound and the amine used to form the following imines.
(d)
(e)
(f)

Verified step by step guidance

Step 1: Understand the reaction that forms imines. Imines are formed by the condensation reaction between a carbonyl compound (aldehyde or ketone) and a primary amine. During this reaction, the oxygen from the carbonyl group is replaced by the nitrogen from the amine, forming a C=N bond.

Step 2: Analyze structure (a). The imine shown has a C=N bond within a bicyclic structure. To deduce the starting materials, identify the carbon atom bonded to the nitrogen in the imine. This carbon was originally part of a carbonyl group (likely a ketone). The nitrogen atom came from a primary amine. The carbonyl compound would be cyclohexanone, and the amine would be cyclohexylamine.

Step 3: Analyze structure (b). The imine shown has a C=N bond within a bicyclic structure similar to (a). The carbonyl compound would again be cyclohexanone, but the amine would be a different primary amine, specifically cyclohexylamine with a different substitution pattern.

Step 4: Analyze structure (c). The imine shown has a C=N bond attached to a benzene ring and a methyl group on the nitrogen. The carbonyl compound would be benzaldehyde (an aldehyde with a benzene ring), and the amine would be methylamine (a primary amine with a single methyl group).

Step 5: Summarize the process. For each imine, identify the carbonyl compound and the amine by analyzing the structure of the imine and tracing back to the original reactants. This involves recognizing the C=N bond and determining the source of the carbon and nitrogen atoms in the imine.

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Key Concepts

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

Carbonyl Compounds

Carbonyl compounds are organic molecules characterized by the presence of a carbonyl group (C=O). This functional group is pivotal in organic chemistry as it participates in various reactions, including nucleophilic addition, which is essential for forming imines. Common examples include aldehydes and ketones, which can react with amines to produce imines.

Imines

Imines are a class of compounds formed by the reaction of a carbonyl compound with an amine, resulting in a C=N bond. This reaction typically involves the nucleophilic attack of the amine on the carbonyl carbon, followed by the elimination of water. Imines are important intermediates in organic synthesis and can be further transformed into various functional groups.

Amines

Amines are organic compounds derived from ammonia (NH3) by replacing one or more hydrogen atoms with alkyl or aryl groups. They can act as nucleophiles due to the lone pair of electrons on the nitrogen atom, allowing them to react with electrophiles such as carbonyl compounds. Understanding the structure and reactivity of amines is crucial for predicting their behavior in imine formation.

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