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Compound (A) ,C(8)H(9)Br gives a white ...

Compound (A) ,`C_(8)H_(9)Br` gives a white precipitate when warmed with alcoholic `AgNO_(3)` Oxidation of (A) gives an acid (B) `C_(8)H_(6)O_(4)` (B) easily forms anhydride on heating Identify the compound (A)

A

B

C

D

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The correct Answer is:
D
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Compund (A)C_(8)H_(9) Br gives a white precipitate when warmed with alcoholic AgNO_(3) Oxidation of (A) gives an acid (B) C_(8) H_(6)O_(4) (B) easily anhydride on heating Identify the compound (A) .

An organic compound (A) (C_(8)H_(14)O) forms an oxime and gives a positive haloform reaction. On ozonolysis, it gives acetone and a compound (B) (C_(5)H_(8)O_(2)) . (B) forms a dioxime and on subjecting to oxidation reaction gives an acid (C ) (C_(4)H_(6)O_(4)) . On treatment with excess of ammonia and strong heating, (C ) gives a neutral compound (D) (C_(4)H_(5)O_(2)N) . (D) on distillation with zinc dust forms pyrrloe. Suggest the possible structures of (A), (B), (C ), and (D). Explain the chemical reactions involved.

Compound (A) and (B) are isomers having C_(8)H_(10) . On oxidation (A) gives benzoic acid while (B) gives phthalic acid which forms an anhydride (C) on heating. Identify (A), (B) and (C).