Aldehydes And Ketones Question 11

Question 11 - 01 February - Shift 1

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

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Answer: (2)

Solution:

Formula: Hydrogenation

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.