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

29. Amino Acids

Proteins and Amino Acids

Organic Chemistry

29. Amino Acids

Proteins and Amino Acids

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2:40 minutes

Problem 29e

Textbook Question

Predict the products of the following reactions.
(e)

Verified step by step guidance

Step 1: Identify the functional group in the starting material. The given compound is a ketone, specifically 2-butanone, with a carbonyl group (C=O) as the reactive site.

Step 2: Analyze the reagents provided. The reaction involves NH₃ (ammonia), HCN (hydrogen cyanide), and H₂O (water). This suggests a cyanohydrin formation followed by hydrolysis.

Step 3: Predict the first step of the reaction. The carbonyl group reacts with HCN to form a cyanohydrin. The nucleophilic attack of the cyanide ion (CN⁻) on the carbonyl carbon generates a hydroxyl group (-OH) and a nitrile group (-CN) attached to the same carbon.

Step 4: Predict the second step of the reaction. The cyanohydrin undergoes hydrolysis in the presence of water, converting the nitrile group (-CN) into a carboxylic acid (-COOH). This results in the formation of an α-hydroxycarboxylic acid.

Step 5: Summarize the product. The final product is an α-hydroxycarboxylic acid derived from 2-butanone, where the hydroxyl group (-OH) and carboxylic acid group (-COOH) are attached to the same carbon atom.

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Key Concepts

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

Nucleophilic Addition Reactions

Nucleophilic addition reactions involve the attack of a nucleophile, such as ammonia (NH3) or cyanide (HCN), on an electrophilic carbon atom, typically found in carbonyl compounds. This reaction results in the formation of a new bond between the nucleophile and the carbon, leading to the generation of an intermediate that can further react to yield various products.

Amino Acids and Their Reactions

Amino acids are organic compounds that contain both an amino group and a carboxylic acid group. In the presence of nucleophiles like NH3 or HCN, amino acids can undergo reactions that modify their functional groups, potentially leading to the formation of new compounds such as amines or α-amino nitriles, depending on the reaction conditions.

Hydrolysis of Nitriles

Hydrolysis of nitriles involves the reaction of nitriles with water, often in the presence of an acid or base, to convert them into carboxylic acids or amides. This reaction is significant in organic synthesis as it allows for the transformation of nitrile intermediates, which can be formed during nucleophilic addition reactions, into more functionalized products.