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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2:42 minutes

Problem 23d

Textbook Question

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

Verified step by step guidance

Step 1: Analyze the given derivative structure. The molecule consists of a hydrazone functional group (-C=N-NH-) formed by the reaction of a carbonyl compound and a hydrazine derivative. Additionally, the hydrazine derivative contains a nitro-substituted benzene ring.

Step 2: Identify the carbonyl compound. The left side of the molecule shows a cyclohexanone structure, which is a ketone with a six-membered ring. This indicates that cyclohexanone is the carbonyl compound involved in the reaction.

Step 3: Identify the amine component. The hydrazone group suggests that the amine component is a hydrazine derivative. The right side of the molecule shows a nitro-substituted benzene ring attached to the hydrazine group. This indicates that the amine component is 2,4-dinitrophenylhydrazine.

Step 4: Understand the reaction mechanism. The reaction involves the nucleophilic attack of the hydrazine derivative (2,4-dinitrophenylhydrazine) on the carbonyl group of cyclohexanone, followed by the elimination of water to form the hydrazone derivative.

Step 5: Summarize the reactants. The amine component is 2,4-dinitrophenylhydrazine, and the carbonyl compound is cyclohexanone. These two reactants combine to form the given hydrazone 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 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.

Imine Formation

Imine formation occurs when an amine reacts with a carbonyl compound, typically an aldehyde or ketone, resulting in the creation of an imine (R1R2C=NR3). This reaction 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 further undergo transformations to yield other functional groups.

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