JEE Main 2021 · 18 March · evening · Single correct · +4 / −1
Main products formed during a reaction of 1-methoxy naphthalene with hydroiodic acid are :
- (a)
- (b)
- (c)
- (d)
Answer and solution
Answer (d)
Solution
Chemistry ma’am · 4 steps
With an aryl methyl ether, iodide always attacks the methyl carbon, never the ring carbon.
- Protonate the oxygen. HI first protonates the ether oxygen. This turns the -OCH₃ group into a good leaving group: the C–O bond can now break and leave a neutral -OH.
- Pick the bond. The ring C–O bond has partial double-bond character from resonance, and its carbon is sp², so I⁻ cannot do backside attack there. An aryl cation is also far too unstable to form. The methyl carbon is small and unhindered, so I⁻ attacks it by S_N2.
C₁₀H₇-O-CH₃ + HI → C₁₀H₇-OH + CH₃I
- Naphthol stays. Even with excess HI, 1-naphthol does not turn into 1-iodonaphthalene, for the same reason: its C–O bond is on an sp² ring carbon and does not break.
- So. The main products are 1-naphthol and CH₃I, which is option (d).
The idea to keep. Cleaving an aryl alkyl ether with HI always gives a phenol and an alkyl iodide. The aryl–O bond never breaks, because the ring carbon is sp² and has partial double-bond character.
Answer from the NTA final answer key. Solution by PrepWiser.