question_answer

Direction (Q. Nos. 55): An organic compound [A] \[{{C}_{7}}{{H}_{6}}O\] gives positive test with Tollen's reagent. On treatment with alcoholic \[C{{N}^{\odot -}}\] [A] gives the compound [B]\[{{C}_{14}}{{H}_{12}}{{O}_{2}}\]. Compound [B] on reduction with \[Zn-Hg,\,\,HCl\] and dehydration gives an unsaturated compound [C], which adds one mole of\[B{{r}_{2}}/CC{{l}_{4}}\]. The compound [B] can be oxidized with \[HN{{O}_{3}}\] to a compound [D] \[{{C}_{14}}{{H}_{10}}{{O}_{2}}\]. Compound [D] on heating with KOH undergoes rearrangement and subsequent acidification of rearranged products yields an acidic compound (E) \[{{C}_{14}}{{H}_{12}}{{O}_{3}}\].

Structure of compound (E) is

A)

B)

C)                                           

D)

Correct Answer: D

Solution :