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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2:10 minutes

Problem 22a

Textbook Question

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

Verified step by step guidance

Step 1: Understand the reaction mechanism. The reaction between a carbonyl compound and NaCN/HCN involves the nucleophilic addition of the cyanide ion (CN⁻) to the carbonyl carbon, forming a cyanohydrin.

Step 2: Identify the structure of the cyanohydrin product. Analyze the given image to determine the structure of the cyanohydrin, focusing on the functional groups and the carbon skeleton.

Step 3: Determine the carbonyl precursor. Since cyanohydrins are formed by the addition of CN⁻ to the carbonyl carbon, the carbonyl compound should have the same carbon skeleton as the cyanohydrin minus the CN group.

Step 4: Consider the stereochemistry. If the cyanohydrin has chiral centers, consider the stereochemistry of the starting carbonyl compound, as it can influence the stereochemistry of the product.

Step 5: Suggest the carbonyl compound. Based on the analysis, suggest a carbonyl compound (either an aldehyde or ketone) that would react with NaCN/HCN to yield the cyanohydrin with the desired structure.

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Key Concepts

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

Carbonyl Compounds

Carbonyl compounds, characterized by the presence of a carbon-oxygen double bond (C=O), include aldehydes and ketones. They are highly reactive due to the electrophilic nature of the carbon atom, making them susceptible to nucleophilic attack. Understanding the structure and reactivity of carbonyls is essential for predicting their behavior in reactions, such as those with nucleophiles like cyanide.

Nucleophilic Addition

Nucleophilic addition is a fundamental reaction mechanism in organic chemistry where a nucleophile attacks an electrophilic carbon atom, leading to the formation of a new bond. In the case of carbonyl compounds, nucleophiles such as NaCN or HCN can add to the carbonyl carbon, resulting in the formation of cyanohydrins. This mechanism is crucial for understanding how to synthesize various organic compounds from carbonyl precursors.

Cyanohydrins

Cyanohydrins are organic compounds formed by the addition of hydrogen cyanide (HCN) to carbonyl compounds, resulting in a hydroxyl group (-OH) and a cyano group (-CN) attached to the same carbon atom. They are important intermediates in organic synthesis and can be further transformed into various functional groups. Recognizing the structure and properties of cyanohydrins is vital for predicting their reactivity and potential applications in organic chemistry.

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Related Practice

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

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

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

How would you synthesize the cyanohydrin shown?

Textbook Question

Which of the following secondary alcohols can be prepared by the reaction of methyl formate with excess Grignard reagent?

Textbook Question

Show how the following compounds can be synthesized from cyclohexanol.

a. b. c.

Textbook Question

Propose a mechanism for each of the following reactions: