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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3:02 minutes

Problem 53c

Textbook Question

Predict the products formed when cyclohexanone reacts with the following reagents.
(c) hydroxylamine and weak acid

Verified step by step guidance

Identify the functional group in cyclohexanone. Cyclohexanone is a ketone, which contains a carbonyl group (C=O) attached to a six-membered cyclohexane ring.

Understand the role of hydroxylamine (NH2OH). Hydroxylamine is a nucleophile that reacts with carbonyl compounds to form oximes. This reaction typically occurs in the presence of a weak acid, which helps to protonate the carbonyl oxygen and make the carbonyl carbon more electrophilic.

Protonate the carbonyl oxygen of cyclohexanone using the weak acid. This step increases the electrophilicity of the carbonyl carbon, making it more susceptible to nucleophilic attack by hydroxylamine.

Perform the nucleophilic attack. The lone pair of electrons on the nitrogen atom of hydroxylamine attacks the electrophilic carbonyl carbon, forming a tetrahedral intermediate.

Eliminate water (H2O) from the intermediate to form the final product. The result is an oxime, specifically cyclohexanone oxime, where the carbonyl group is replaced by a C=N-OH functional group.

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Key Concepts

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

Nucleophilic Addition

Nucleophilic addition is a fundamental reaction mechanism in organic chemistry where a nucleophile attacks an electrophilic carbon atom, typically found in carbonyl compounds like ketones and aldehydes. In the case of cyclohexanone, the carbonyl carbon is susceptible to attack by nucleophiles such as hydroxylamine, leading to the formation of an intermediate that can further react to yield a product.

Hydroxylamine

Hydroxylamine (NH2OH) is a nucleophilic reagent commonly used to convert carbonyl compounds into oximes. When cyclohexanone reacts with hydroxylamine in the presence of a weak acid, the hydroxylamine attacks the carbonyl carbon, resulting in the formation of a cyclohexanone oxime, which is characterized by the presence of the C=N-OH functional group.

Weak Acid Catalysis

Weak acid catalysis involves the use of a weak acid to facilitate a reaction without significantly altering the pH of the solution. In the reaction of cyclohexanone with hydroxylamine, a weak acid can help protonate the hydroxylamine, enhancing its nucleophilicity and promoting the formation of the oxime product. This catalytic effect can improve the reaction rate and yield.

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