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JEE Main & Advanced Chemistry Aldehydes, Ketones Question Bank Critical Thinking Aldehydes,

  • question_answer
    Compound ?A? (molecular formula \[{{C}_{3}}{{H}_{8}}O)\] is treated with acidified potassium dichromate to form a product ?B? (molecular formula \[{{C}_{3}}{{H}_{6}}O).\] ?B? forms a shining silver mirror on warming with ammoniacal silver nitrate. ?B? when treated with an aqueous solution of \[{{H}_{2}}NCONHN{{H}_{2}}.HCl\] and sodium acetate gives a product ?C?. Identify the structure of ?C?                 [IIT-JEE (Screening) 2002]

    A)                 \[C{{H}_{3}}C{{H}_{2}}CH=NNHCON{{H}_{2}}\]

    B)                 \[C{{H}_{3}}-CH=\underset{C{{H}_{3}}}{\mathop{\underset{|\,\,\,\,\,\,\,\,\,\,}{\mathop{NNH}}\,}}\,CON{{H}_{2}}\]

    C)                 \[C{{H}_{3}}CH=\underset{C{{H}_{3}}}{\mathop{\underset{|\,\,\,\,\,\,\,\,\,\,}{\mathop{NCO}}\,}}\,NHN{{H}_{2}}\]

    D)                 \[C{{H}_{3}}C{{H}_{2}}CH-NCONHN{{H}_{2}}\]

    Correct Answer: A

    Solution :

               \[\underset{\text{(A)}}{\mathop{C{{H}_{3}}-C{{H}_{2}}-C{{H}_{2}}OH}}\,\xrightarrow{[O]}\underset{\text{(B)}}{\mathop{C{{H}_{3}}-C{{H}_{2}}-CHO}}\,\]            \[C{{H}_{3}}-C{{H}_{2}}-\overset{H}{\mathop{\overset{|}{\mathop{C}}\,}}\,=O+{{H}_{2}}NNHCON{{H}_{2}}\xrightarrow{HCl}\] \[C{{H}_{3}}C{{H}_{2}}CH=N-NHCON{{H}_{2}}\]


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