Given below are two statements : Statement (I) : Vanillin (see structure) will react with NaOH and also with Tollen's reagent. Statement (II) : (see structure) will undergo self aldol condensation very easily. In the light of the above statements, choose the most appropriate answer from the options given below :
(A)Statement I is incorrect but Statement II is correct
(B)Statement I is correct but Statement II is incorrect✓ Correct
(C)Both Statement I and Statement II are incorrect
(D)Both Statement I and Statement II are correct
Answer: (B)
Solution
Vanillin carries a phenolic hydroxyl, which dissolves in sodium hydroxide, and an aldehyde group, which reduces Tollens' reagent to a silver mirror, so the first statement holds. Its aldehyde carbon, however, is bonded directly to the aromatic ring and has no α-hydrogen, the adjacent carbon being part of the ring. With no α-hydrogen there is no enolate and self aldol condensation cannot occur, so the second statement fails. The first statement is correct and the second is incorrect.
JEE Main · 2025 · 02 Apr 2025 · Shift 1 · Single correct option
