An organic compound (A) has the molecular formula C8H9Br and on warming with alcoholic AgNO3 it produces a yellow precipitate. When (A) is oxidized, it yields an acid (B) with formula C8H6O4. Acid (B) readily cyclizes to its anhydride on heating. Which of the following is compound (A)?

Question

Accepted Answer

o-CH3C6H4CH2Br. A gives AgBr (benzylic C-H2Br) with alcoholic AgNO3; oxidation of both the CH3 and CH2Br groups of o-CH3C6H4CH2Br gives o-phthalic acid C8H6O4, which readily forms phthalic anhydride on heating. A para isomer would give terephthalic acid, which does not cyclize.

An organic compound (A) has the molecular formula C8H9Br and on warming with alcoholic AgNO3 it produces a yellow precipitate. When (A) is oxidized, it yields an acid (B) with formula C8H6O4. Acid (B) readily cyclizes to its anhydride on heating. Which of the following is compound (A)?

Solution

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