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.
We need to determine the mechanism and major product for the reaction of sodium phenoxide with methyl iodide ($$\text{CH}_3\text{I}$$).
Nucleophilic Attack via $$\text{S}_\text{N}2$$ Pathway:
The reaction between sodium phenoxide ($$\text{Ph--O}^\ominus\text{Na}^\oplus$$) and methyl iodide ($$\text{CH}_3\text{I}$$) is a classic example of a Williamson ether synthesis. The strongly nucleophilic phenoxide oxygen atom attacks the relatively unhindered primary carbon atom of the methyl iodide electrophile:
$$\text{Ph--O}^\ominus + \text{CH}_3\text{--I} \xrightarrow{\text{S}_\text{N}2} \text{Ph--O--CH}_3 + \text{I}^\ominus$$Transition State and Displacement:
As the nucleophilic oxygen atom forms a new covalent bond with the methyl group, the iodide ion simultaneously departs as an excellent leaving group ($$-\text{NaI}$$), yielding 2-methoxy-1-methylbenzene (or anisole depending on ring substitutions).
The reaction cleanly proceeds via a bimolecular nucleophilic substitution ($$\text{S}_\text{N}2$$) process to give the corresponding alkyl aryl ether.
Answer: Option B (2-methoxy-1-methylbenzene formed via S$$_\text{N}$$2 reaction)
Click on the Email ☝️ to Watch the Video Solution
Create a FREE account and get:
Educational materials for JEE preparation