Q22 / 90 · JEE Main 2023 (01 Feb Shift 1) · Chemistry

Number of isomeric compounds with molecular formula C9H10O which

(i) do not dissolve in NaOH
(ii) do not dissolve in HCl.

(iii) do not give orange precipitate with 2,4 - DNP

(iv) on hydrogenation give identical compound with molecular formula C9H12O is

Correct answer: 2

Solution

No reaction with strong base or acid indicates presence of strong neutrality or non-reactive functional hroup with a single oxygen. No positive 2,4-DNP test indicates absence of carbonyl compound. Same compound formation upon hydrogenation indicates single double bond. Thus, it is an ether.

As per the language of given question, the best possible isomeric structure is Ph-CH=CH-O-CH3 (cis and trans). So, the answer is 2.

Hence, the correct answer is 2.

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