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

Verified step by step guidance

1. 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.
2. 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.
3. 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.
4. 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.
5. 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.

Key Concepts

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.