A trisubstituted compound ' A ', C 10 H 12 O 2 gives neutral FeCl 3 test positive. Treatment of…

A trisubstituted compound 'A', C10H12O2 gives neutral FeCl3 test positive. Treatment of compound 'A' with NaOH and CH3Br gives C11H14O2, with hydroiodic acid gives methyl iodide and with hot conc. NaOH gives a compound B, C10H12O2. Compound 'A' also decolorises alkaline KMnO4. The number of π bond/s  present in the compound 'A' is _____ .

Solution

The trisubstituted compound 'A', C10H12O2 gives neutral FeCl3 test positive, means the compound is phenol. Phenol on treatment with NaOH and CH3Br gives C10H11O2CH3. The given compound is reacting with hot conc. NaOH gives a compound B, C10H12O2. The reaction is Cannizzaro's reaction. Hence, compound must be benzaldehyde derivative. Compound 'A' also decolourises alkaline KMnO4, means compound contains an alkyl group attached to benzene ring. Hence, the structure of the compound can be written as follows,

The reactions are shown below.

Asked in: JEE Main 2023 (30 Jan Shift 1)

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