Question

The rates of alkaline hydrolysis of the compounds shown below follow the order: 

• A. I \(>\) II \(>\) III
• B. II \(>\) I \(>\) III
• C. II \(>\) III \(>\) I
• D. III \(>\) I \(>\) II

Hint:

Compounds with better leaving groups, like esters, generally undergo faster hydrolysis. Additionally, sterically hindered groups can increase the reactivity in hydrolysis.

Answer 1

The Correct Option is C

In this question, we are asked to determine the order of alkaline hydrolysis rates of the compounds I, II, and III. Alkaline hydrolysis typically proceeds faster for compounds with better leaving groups and higher steric accessibility.
- Compound I has an amide group (-CONH\(_2\)), which is generally more resistant to hydrolysis due to its stability and the poor leaving ability of the amide group.
- Compound II has an ester group (-COOEt), which is more reactive than the amide group but less reactive than other groups like halides.
- Compound III also has an ester group but is likely more reactive than II due to the steric accessibility provided by the tert-butyl groups.
Thus, the order of reactivity is: II > III > I.