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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4:13 minutes

Problem 16

Textbook Question

Can a cyanohydrin be prepared by treating a ketone with sodium cyanide?

Verified step by step guidance

Identify the functional groups involved: A cyanohydrin is formed from a ketone or aldehyde and contains a hydroxyl group (-OH) and a cyano group (-CN) attached to the same carbon.

Understand the reaction mechanism: The reaction involves nucleophilic addition of the cyanide ion (CN⁻) to the carbonyl carbon of the ketone.

Consider the role of sodium cyanide: Sodium cyanide (NaCN) provides the cyanide ion (CN⁻) necessary for the nucleophilic attack on the carbonyl carbon.

Recognize the conditions required: The reaction typically occurs in the presence of an acid, such as HCl, to protonate the oxygen and stabilize the intermediate, leading to the formation of the cyanohydrin.

Conclude the feasibility: Yes, a cyanohydrin can be prepared by treating a ketone with sodium cyanide under the appropriate acidic conditions.

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Key Concepts

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

Cyanohydrin Formation

Cyanohydrins are organic compounds formed when a carbonyl compound, such as an aldehyde or ketone, reacts with hydrogen cyanide (HCN) or a cyanide salt. This reaction involves the nucleophilic addition of the cyanide ion to the carbonyl carbon, leading to the formation of a hydroxyl group and a cyano group on the same carbon atom.

Nucleophilic Addition

Nucleophilic addition is a fundamental reaction mechanism in organic chemistry where a nucleophile attacks an electrophilic carbon atom, typically found in carbonyl groups. In the case of cyanohydrin formation, the cyanide ion acts as the nucleophile, attacking the electrophilic carbon of the ketone, resulting in the formation of a new carbon-carbon bond.

Role of Sodium Cyanide

Sodium cyanide (NaCN) is a source of cyanide ions in organic reactions. When treating a ketone with sodium cyanide, the cyanide ion generated can effectively participate in nucleophilic addition to the carbonyl group of the ketone, facilitating the formation of a cyanohydrin. This reaction is significant in organic synthesis for introducing functional groups into molecules.

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Related Practice

Textbook Question

For each compound,

1. name the functional group.

2. show what compound(s) result from complete hydrolysis.

(h)

Textbook Question

Show how you would synthesize the following derivatives from appropriate carbonyl compounds.

(b)

Textbook Question

Identify A through O:

Textbook Question

Identify the bonds broken and formed in the following addition reaction.

(a) Would you expect this reaction to be favored based on entropy?

(b) Based on enthalpy [qualitatively]?

Textbook Question

The following reaction is known as the benzoin condensation. The reaction does not take place if sodium hydroxide is used instead of sodium cyanide. Propose a mechanism for the reaction and explain why the reaction does not occur if hydroxide ion is the base.

Textbook Question

Predict the products formed when cyclohexanone reacts with the following reagents.

(k) sodium cyanide

Textbook Question

Suggest a carbonyl to react with NaCN/HCN to produce the following cyanohydrins.

(a)

Textbook Question

How would you synthesize the cyanohydrin shown?

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