Sign in
Please select an account to continue using cracku.in
↓ →
Join Our JEE Preparation Group
Prep with like-minded aspirants; Get access to free daily tests and study material.
Alkaline hydrolysis of ester follow $$SN_2$$ mechanism.
Alkaline hydrolysis of an ester proceeds via a nucleophilic acyl substitution ($$\text{B}_{\text{Ac}}2$$) mechanism. The rate-determining step involves the attack of the hydroxide nucleophile ($$\text{OH}^\ominus$$) on the electrophilic carbonyl carbon:
$$\text{Rate of Hydrolysis} \propto \text{Electrophilicity of the Carbonyl Carbon}$$
Compound III ($$\text{--NO}_2$$ at para position):
The nitro group is a very strong electron-withdrawing group via both resonance ($$\text{--R}$$) and inductive ($$\text{--I}$$) effects. This creates the highest positive charge on the carbonyl carbon, making III the most reactive.
Compound II ($$\text{--Cl}$$ at para position):
The chlorine atom acts as an electron-withdrawing group primarily through its inductive ($$\text{--I}$$) effect, which outweighs its weak resonance donation. It increases the reactivity compared to the unsubstituted ester, but less than the nitro group.
Compound I (Unsubstituted Benzene Ring, $$\text{--H}$$):
The unsubstituted ester serves as the standard baseline reference with no additional electronic enhancement or attenuation.
Compound IV ($$\text{--OCH}_3$$ at para position):
The methoxy group is a powerful electron-donating group due to resonance ($$\text{+R}$$) from the lone pairs on the oxygen atom. This severely reduces the electrophilicity of the carbonyl carbon, making IV the least reactive.
Combining these trends gives the clear decreasing sequence of reactivity: III > II > I > IV.
Answer: Option B — III > II > I > IV
Click on the Email ☝️ to Watch the Video Solution
Create a FREE account and get:
Educational materials for JEE preparation