An organic compound [A], molecular formula C10H20O2 was hydrolyzed with dilute sulphuric acid to give a carboxylic acid [B] and an alcohol [C]. Oxidation of [C] with CrO3 - H2SO4 produced [B]. Which of the following strucutres are not possible for [A]?

Question

An organic compound [A], molecular formula C₁₀H₂₀O₂ was hydrolyzed with dilute sulphuric acid to give a carboxylic acid [B] and an alcohol [C]. Oxidation of [C] with
CrO₃ - H₂SO₄ produced [B]. Which of the following strucutres are not possible for [A]?

(CH₃)₃ – C – COOCH₂C(CH₃)₃

CH₃CH₂CH₂COOCH₂CH₂CH₂CH₃

Solution

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