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JEE Main20231 Feb 2023Morning ShiftChemistryAldehydes and KetonesActual

Number of isomeric compounds with molecular formula C 9 H 10 O 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 C 9 H 12 O is

Correct answer

2

Step-by-step 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 - CH 3 (cis and trans). So, the answer is 2 .

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