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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1:08 minutes

Problem 29f

Textbook Question

Predict the products of the following reactions.
(f)

Verified step by step guidance

Step 1: Identify the functional groups in the reactant. The molecule contains an amine group (-NH2) and a nitrile group (-CN). The reaction involves hydrolysis under acidic conditions (H3O+ and heat).

Step 2: Understand the mechanism of nitrile hydrolysis. Under acidic conditions, the nitrile group (-CN) is converted into a carboxylic acid (-COOH) through intermediate formation of an imidic acid and subsequent tautomerization.

Step 3: Consider the stability of the amine group (-NH2) under acidic conditions. The amine group is protonated to form an ammonium ion (-NH3+), but it remains intact during the reaction.

Step 4: Predict the product structure. The nitrile group (-CN) is replaced by a carboxylic acid group (-COOH), while the amine group (-NH2) remains attached to the same carbon atom.

Step 5: Verify the stereochemistry and connectivity of the product. The original carbon skeleton is preserved, and the final product is an amino acid with both an amine group (-NH2) and a carboxylic acid group (-COOH) on 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

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 this case, the amino group (NH2) acts as a nucleophile, attacking the carbon atom of the nitrile (CN) group, which is electrophilic due to the triple bond's polarity.

Hydrolysis of Nitriles

Hydrolysis of nitriles involves the reaction of a nitrile with water, often in the presence of an acid or base, to convert it into a carboxylic acid. In this reaction, the nitrile group is transformed into a carboxylic acid through the addition of water, facilitated by the acidic conditions provided by H3O+.

Acid-Base Catalysis

Acid-base catalysis refers to the acceleration of a chemical reaction by the presence of an acid or base. In this scenario, H3O+ serves as an acid that protonates the nitrile, making it more susceptible to nucleophilic attack by the amino group, thus enhancing the reaction rate and product formation.