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

Acid-Catalyzed Ester Hydrolysis

Organic Chemistry

22. Carboxylic Acid Derivatives: NAS

Acid-Catalyzed Ester Hydrolysis

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4:41 minutes

Problem 58c,d

Textbook Question

What reagents would you use to convert methyl propanoate to the following compounds?
c. N-ethylpropanamide
d. propanoic acid

Verified step by step guidance

Step 1: To convert methyl propanoate to N-ethylpropanamide, perform an aminolysis reaction. Use ethylamine (CH3CH2NH2) as the nucleophile. The ester group in methyl propanoate will react with ethylamine to form the amide bond.

Step 2: Ensure the reaction is carried out under mild heating conditions to facilitate the nucleophilic attack of ethylamine on the carbonyl carbon of the ester group.

Step 3: To convert methyl propanoate to propanoic acid, perform hydrolysis of the ester. Use aqueous acid (e.g., HCl) or aqueous base (e.g., NaOH) as the reagent.

Step 4: If using acidic hydrolysis, the ester will be protonated, making the carbonyl carbon more electrophilic, followed by nucleophilic attack by water. This leads to the formation of propanoic acid and methanol as by-products.

Step 5: If using basic hydrolysis, the ester reacts with hydroxide ions to form the carboxylate salt, which can be acidified later to yield propanoic acid.

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Key Concepts

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

Ester Hydrolysis

Ester hydrolysis is a reaction where an ester reacts with water to form an alcohol and a carboxylic acid. This reaction can be catalyzed by an acid or base and is essential for converting esters like methyl propanoate into their corresponding acids, such as propanoic acid. Understanding this process is crucial for identifying the reagents needed for the conversion.

Amide Formation

Amide formation involves the reaction of a carboxylic acid or its derivative with an amine, resulting in the formation of an amide. In the case of converting methyl propanoate to N-ethylpropanamide, an amine (ethylamine) is reacted with the acid derivative. This concept is vital for determining the appropriate reagents for synthesizing amides from esters.

Nucleophilic Acyl Substitution

Nucleophilic acyl substitution is a fundamental reaction mechanism in organic chemistry where a nucleophile attacks the carbonyl carbon of an acyl compound, leading to the substitution of a leaving group. This mechanism is key in both ester hydrolysis and amide formation, as it explains how nucleophiles like water or amines can replace the ester group in the reaction.

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What reagents would you use to convert methyl propanoate to the following compounds? c. N-ethylpropanamide d. propanoic acid

Key Concepts

Ester Hydrolysis

Amide Formation

Nucleophilic Acyl Substitution

Watch next

What reagents would you use to convert methyl propanoate to the following compounds?
c. N-ethylpropanamide
d. propanoic acid