Question

Draw both major organic product(s) that are obtained when 4-chloro-2-methyltoluene is treated with sodium amide followed by treatment with H3O+.

Answer 1

Answer:

I attached the answer as an image. I also drew in the two most acidic hydrogens.

Explanation:

This goes through the 'benzyne' intermediate, meaning it does an E2-looking reaction by expelling a leaving group (chloride) from the adjacent part of the ring using the amide as a strong base. The triple-bonded benzyne has absurd bond angle strain, and is vulnerable to a good nucleophile like an amide ion, and the resultant sp2 anion is then reprotonated by the acid. I didn't draw in the acid-base reaction in step one, or the spectator ion (sodium).