Aromatic Aldehydes Ketones And Acids Result Question 34

  1. Five isomeric para-disubstituted aromatic compounds $A$ to $E$ with molecular formula $\mathrm{C} _8 \mathrm{H} _8 \mathrm{O} _2$ were given for identification.

Based on the following observations, give structures of the compounds :

(i) Both $A$ and $B$ form a silver mirror with Tollen’s reagent; also, $B$ gives a positive test with $\mathrm{FeCl} _3$ solution.

(ii) $C$ gives positive iodoform test .

(iii) $D$ is readily extracted in aqueous $\mathrm{NaHCO} _3$ solution.

(iv) $E$ on acid hydrolysis gives $1, 4$ -dihydroxy benzene.

(2002, Main, 5M)

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Solution:

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