An orgnic compound (A) contains `79.25%` C, `5.66%` H, and `15.09%` O. It has a vapour density of 53 and reduces the Tollens reagent. Action of NaOH on (A) produces (B) and (C ). (B) on controlled oxidation gives (A) which on further oxidation produces (C ). (C ) on distillation with `PCl_(5)` gives (D). (D) reacts with aq. `NH_(3)` giving (E ) which reacts with `NaOH` and `Br_(2)` forming (F). The latter on reaction which hypo-phoshorus acid yield (H). Identify the compounds (A) to (H).

Explanation

`C =(79.25)/(12)`, `H =(5.66)/(1)`, `O =(15.09)/(16)`
`=6.604` `=5.66` `=0.81`
Simplest formula `(6.6)/(0.81)`, `(5.66)/(0.81)`, `(0.81)/(0.81)`
Formula `=C_(7)H_(6)O=84+6+16=106`
V.D. = 53, Mw = 106
Degree of unsaturation `=C_(7)H_(6)`
`(C_(7)H_(16)=H_(16)-H_(6)=H_(10))`
`=5^(@)` unsaturation `=4^(@)` (due to benzene) and `1^(@)` (due to aldehyde).