4.An organic compound( A )having molecular formula C9H10O forms an organic red precipitate (B) with 2;4 DNP reagent . compound( A )gives yellow precipitate (C) when heated in the presence of iodine and NaOH along With colourless compound (D) .A does not reduce tollen's reagent or Fehling 's solution nor does it decolorizes bromine water . On drastic oxidation of (A )with chromic acid ,a carboxylic acid (E)of molecular Formula C7H6O2 is formed Deduce the structure of the organic compounds (A) to( E )

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Q. An organic compound (A) with molecular formula,

C_{8} H_{8} O

forms an orange-red precipitate with 2,4-DNP reagent and gives yellow precipitate on heating with iodine in the presence of sodium hydroxide.It neither reduces Tollens' or Fehling's reagent, nor does it decolourise bromine water or Baeyer's reagent.On drastic oxidation with chromic acid, it gives a carboxylic acid (B) having molecular formula,

C_{7} H_{6} O_{2}

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C_{8} H_{8} O

forms an orange-red precipitate with 2,4 DNP and gives a yellow precipitate of compound (B) on treatment with iodine and sodium hydroxide solution. Compound (A) does not give Tollen's or Fehling test but on drastic oxidation with potassium permanganate, it gives (C) which on reaction with thionyl chloride gives a compound (D) having formula

C_{7} H_{5} O C l

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R_{2} C d

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C_{3} H_{6} O

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C_{8} H_{8} O

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