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

Cyanohydrin

Organic Chemistry

21. Aldehydes and Ketones: Nucleophilic Addition

Cyanohydrin

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1:27 minutes

Problem 53l

Textbook Question

Predict the products formed when cyclohexanone reacts with the following reagents.
(l) acidic hydrolysis of the product from (k)

Verified step by step guidance

Step 1: Understand the context of the problem. Cyclohexanone is a ketone, and the reaction in part (k) likely involves a transformation of cyclohexanone into a derivative. To proceed, you need to know the product from part (k). If part (k) involves a reaction like the formation of an imine or an enamine, this will influence the outcome of the acidic hydrolysis.

Step 2: Recall the general mechanism of acidic hydrolysis. Acidic hydrolysis typically involves the addition of water in the presence of an acid catalyst to break bonds such as imine (C=N) or enamine (C=C-N) bonds, regenerating the original carbonyl compound (in this case, cyclohexanone) and releasing the amine or ammonia.

Step 3: If the product from part (k) is an imine (R2C=NR'), the acidic hydrolysis will involve protonation of the imine nitrogen, followed by nucleophilic attack by water. This will lead to the formation of a tetrahedral intermediate, which will collapse to regenerate the ketone (cyclohexanone) and release the amine (R'NH2).

Step 4: If the product from part (k) is an enamine (R2C=C-NR2'), the acidic hydrolysis will involve protonation of the enamine double bond, followed by water addition to form a carbinolamine intermediate. This intermediate will then collapse to regenerate the ketone (cyclohexanone) and release the secondary amine (R2'NH).

Step 5: Summarize the expected products. The acidic hydrolysis of the product from part (k) will regenerate cyclohexanone and release the corresponding amine or ammonia, depending on the specific structure of the product from part (k). Ensure you understand the mechanism and intermediates involved in the hydrolysis process.

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Key Concepts

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

Cyclohexanone Reactivity

Cyclohexanone is a cyclic ketone that can undergo various reactions due to its carbonyl group. The reactivity of cyclohexanone is influenced by the presence of the carbonyl, which can participate in nucleophilic addition reactions. Understanding how cyclohexanone reacts with different reagents is crucial for predicting the products formed in subsequent reactions.

Acidic Hydrolysis

Acidic hydrolysis is a reaction where a compound reacts with water in the presence of an acid, leading to the cleavage of bonds and the formation of new products. In the context of ketones, this process can lead to the formation of alcohols or carboxylic acids. Recognizing the conditions and mechanisms of acidic hydrolysis is essential for predicting the products of the reaction involving cyclohexanone.

Reaction Mechanisms

Understanding reaction mechanisms is vital in organic chemistry as it explains the step-by-step process by which reactants transform into products. For cyclohexanone and its derivatives, mechanisms such as nucleophilic addition and subsequent protonation steps during acidic hydrolysis must be considered. Familiarity with these mechanisms allows for accurate predictions of the final products formed in the reaction sequence.

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