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JEE Mains · Chemistry · STD 12 - 8.2 Carboxylic acids and their derivative

An organic compound \([A],\) molecular formula \(C _{10} H _{20} O _{2}\) was hydrolyzed with dilute sulphuric acid to give a carboxylic acid \([ B ]\) and alcohol \([C].\) Oxidation of \([C]\) with CrO \(_{3}- H _{2} SO _{4}\) produced \([B].\) Which of the following structures are not possible for \([ A ] ?\)

  1. A \(\left( CH _{3}\right)_{3}- C - COOCH _{2} C \left( CH _{3}\right)_{3}\)
  2. B \(CH _{3} CH _{2} CH _{2} COOCH _{2} CH _{2} CH _{2} CH _{3}\)
  3. C \(\begin{array}{*{20}{c}} {\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,C{H_3}} \\ {\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,|} \\ {C{H_3} - C{H_2} - CH - OCOC{H_2}CH - C{H_2}C{H_3}} \\ {|\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,} \\ {C{H_3}\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,} \end{array}\)
  4. D \(\begin{array}{*{20}{c}} {\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,C{H_3}} \\ {\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,|} \\ {C{H_3} - C{H_2} - CH - COOC{H_2} - CH - C{H_2}C{H_3}} \\ {|\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,} \\ {C{H_3}\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,} \end{array}\)
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(C) \(\begin{array}{*{20}{c}} {\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,C{H_3}} \\ {\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,|} \\ {C{H_3} - C{H_2} - CH - OCOC{H_2}CH - C{H_2}C{H_3}} \\ {|\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,} \\ {C{H_3}\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,} \end{array}\)

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