JEE Main · 2020 · 05 Sep 2020 · Shift 1 · Alcohols Phenols and Ethers

Which of the following derivates of alcohol is unstable is an aqueous base?

(A)(see structure)
(B) $RO - CMe X_{3}$
(C)(see structure)
✓ Correct
(D)(see structure)

Answer: (C)

Solution

Of these oxygen derivatives it is the ester that cannot survive aqueous base. Its carbonyl carbon is electrophilic, so hydroxide attacks it and cleaves the molecule by saponification into a carboxylate and an alcohol. The ethers, the tert-butyl ether among them, carry no such electrophilic centre and are stable to base, so the ester is the unstable one.

JEE Main · 2020 · 05 Sep 2020 · Shift 1 · Single correct option

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