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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2:27 minutes

Problem 23e

Textbook Question

Show what amines and carbonyl compounds combine to give the following derivatives.
(e)

Verified step by step guidance

Step 1: Analyze the given derivative structure. The compound shown is an imine, which is characterized by a C=N bond. Imines are typically formed by the reaction of a primary amine with a carbonyl compound (aldehyde or ketone).

Step 2: Identify the amine component. The nitrogen atom in the imine structure suggests that the amine used in the reaction must have been a primary amine. In this case, the amine is likely benzylamine (C6H5CH2NH2), as the aromatic ring is directly attached to the nitrogen atom.

Step 3: Identify the carbonyl compound. The methyl group attached to the carbon of the C=N bond indicates that the carbonyl compound must have been acetaldehyde (CH3CHO), as it provides the methyl group and the carbonyl functionality.

Step 4: Recall the reaction mechanism. The formation of an imine involves the nucleophilic attack of the amine on the carbonyl carbon, followed by the elimination of water. This condensation reaction results in the formation of the C=N bond.

Step 5: Summarize the components. The amine (benzylamine) and the carbonyl compound (acetaldehyde) combine to form the imine derivative shown in the image. Ensure to understand the reaction conditions, typically requiring mild acid or heat to facilitate the condensation.

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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 known for their basicity and nucleophilicity, making them reactive towards electrophiles, such as carbonyl compounds.

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 differ in the placement of the carbonyl group. Carbonyl compounds are polar and can act as electrophiles, making them susceptible to nucleophilic attack by amines, leading to the formation of various derivatives.

Condensation Reaction

A condensation reaction occurs when two molecules combine to form a larger molecule, with the simultaneous loss of a small molecule, often water. In the context of amines and carbonyl compounds, this reaction typically results in the formation of an imine or an enamine, depending on the specific amine and carbonyl compound involved. Understanding this reaction is crucial for predicting the products formed when these two classes of compounds interact.

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