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Toluene on treatment with CrO3 and (CH3...

Toluene on treatment with `CrO_3` and `(CH_3CO)_2O` followed by hydrolysis with dil. HCl gives

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An organic compound (A) gives opsitive Liebermann reaction and on treatment with CHCI_(3)//KOH followed by hydrolysis gives (B) and (C). Compound (B) gives colour with Schiff's reagent but not (C), which is steam volatile. (C ) on treatment with LiAIH_(4) gives (D), C_(7)H_(8)O_(2) , which on oxidation gives (E). Compound (E) reacts with (CH_(3)CO)_(2))O//CH_(3)COOH to give a pain reliever (F). Give the structures of (A) to (F) with proper reasoning.

Bromobenzene on treatment with fuming H_(2)SO_(4) gives a compound which one treatment with Cl_(2)//AlCl_(3) gives (A), (A) on distillation with dil. H_(2)SO_(4) gives (B). (B) on treatment with an eq. of Mg in dry ether gives (C ). (C ) on treatment with CH_(3)CHO followed by hydrolysis gives (D). (D) on treatment with NaOl gives (E). Identify the structures of (A) to (E).

Bromobenzene on treatment with fuming H_(2)SO_(4) gives a compound which one treatment with Cl_(2)//AlCl_(3) gives (A), (A) on distillation with dil. H_(2)SO_(4) gives (B). (B) on treatment with an eq. of Mg in dry ether gives (C ). (C ) on treatment with CH_(3)CHO followed by hydrolysis gives (D). (D) on treatment with NaOl gives (E). Identify the structures of (A) to (E).

Hydrolysis of CH_(3)CHCl_(2) gives