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

22. Carboxylic Acid Derivatives: NAS

Nucleophilic Acyl Substitution

Organic Chemistry

22. Carboxylic Acid Derivatives: NAS

Nucleophilic Acyl Substitution

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3:00 minutes

Problem 50j

Textbook Question

Predict the products of the following reactions.
(j)

Verified step by step guidance

Step 1: Analyze the first reaction. The starting compound is a nitrile (cyclopentyl nitrile), and the reagents are CH3MgI (a Grignard reagent) followed by H3O+ (acidic hydrolysis). Grignard reagents react with nitriles to form imines, which are then hydrolyzed under acidic conditions to yield ketones.

Step 2: In the first reaction, the CH3MgI adds to the carbon of the nitrile group (C≡N), breaking the triple bond and forming an intermediate imine. The imine is then hydrolyzed by H3O+ to produce a ketone. The final product will be cyclopentyl methyl ketone.

Step 3: Analyze the second reaction. The starting compound is a lactam (cyclic amide), and the reagents are NaOH and H2O. Under basic conditions, lactams undergo hydrolysis to yield the corresponding amino acid.

Step 4: In the second reaction, NaOH breaks the amide bond in the lactam, resulting in the formation of a carboxylate group and an amine group. The product will be 6-aminocaproic acid (the open-chain form of the lactam).

Step 5: Summarize the transformations: (i) Cyclopentyl nitrile reacts with CH3MgI and H3O+ to form cyclopentyl methyl ketone. (ii) The lactam reacts with NaOH and H2O to yield 6-aminocaproic acid.

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Key Concepts

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

Nitrile Reactivity

Nitriles are organic compounds containing a cyano group (-C≡N). They can undergo nucleophilic addition reactions, where a nucleophile attacks the carbon atom of the cyano group. In this case, CH3MgI (a Grignard reagent) acts as a strong nucleophile, adding a methyl group to the nitrile, ultimately leading to the formation of an intermediate that can be hydrolyzed to yield an amine.

Grignard Reagents

Grignard reagents, such as CH3MgI, are organomagnesium compounds that are highly reactive and serve as nucleophiles in organic synthesis. They can react with electrophiles, such as carbonyls and nitriles, to form new carbon-carbon bonds. The reaction with a nitrile results in the formation of an imine intermediate, which can be further hydrolyzed to produce a primary amine after treatment with water or acid.

Hydrolysis of Nitriles

Hydrolysis is the chemical process in which a compound reacts with water, leading to the breakdown of that compound. In the context of nitriles, after the addition of a Grignard reagent, the subsequent treatment with H3O+ (acidic water) facilitates the conversion of the intermediate into a carboxylic acid and an amine. This step is crucial for completing the transformation of the nitrile into a more functionalized product.

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