A) \[{{H}_{3}}C-\overset{\text{O}}{\mathop{\overset{\text{ }\!\!|\!\!\text{ }\!\!|\!\!\text{ }}{\mathop{\text{C}}}\,}}\,-C{{H}_{3}}CH{{l}_{3}}C{{H}_{3}}-C{{H}_{2}}-C{{H}_{3}}\]
B) \[{{\text{H}}_{\text{2}}}\text{C=}\underset{\text{H}}{\mathop{\underset{\text{ }\!\!|\!\!\text{ }}{\mathop{\text{C}}}\,}}\,\text{-C}{{\text{H}}_{\text{2}}}\text{OHC}{{\text{H}}_{\text{3}}}\text{l}{{\text{H}}_{\text{3}}}\text{C-C}{{\text{H}}_{\text{2}}}\]
C) \[\text{-C}{{\text{H}}_{\text{2}}}\text{-OH}\] \[{{\text{H}}_{\text{3}}}\text{C-C}{{\text{H}}_{\text{2}}}\text{-CHO CH}{{\text{l}}_{\text{3}}}\text{ }{{\text{H}}_{\text{3}}}\text{C-}\underset{\text{OH}}{\mathop{\underset{\text{ }\!\!|\!\!\text{ }}{\mathop{\text{C}}}\,}}\,\text{H-C}{{\text{H}}_{\text{3}}}\]
D) \[{{\text{H}}_{\text{3}}}\text{C=}\overset{\text{O}}{\mathop{\overset{\text{ }\!\!|\!\!\text{ }\!\!|\!\!\text{ }}{\mathop{\text{C}}}\,}}\,\text{-C}{{\text{H}}_{\text{3}}}\text{ CH}{{\text{l}}_{\text{3}}}\text{ }{{\text{H}}_{\text{3}}}\text{C-}\underset{\text{OH}}{\mathop{\underset{\text{ }\!\!|\!\!\text{ }}{\mathop{\text{C}}}\,}}\,\text{H-C}{{\text{H}}_{\text{3}}}\]
Correct Answer: A
Solution :
The compound reacts with \[{{l}_{2}}/NaOH,\]so it must be a methyl ketone and it should give iodoform \[(CH{{l}_{3}})\] in this reaction. \[\therefore \]A is \[\text{C}{{\text{H}}_{\text{3}}}\overset{\text{O}}{\mathop{\overset{\text{ }\!\!|\!\!\text{ }\!\!|\!\!\text{ }}{\mathop{\text{C}}}\,}}\,\text{C}{{\text{H}}_{\text{3}}}\text{(acetone)}\] \[C{{H}_{3}}-\underset{A}{\mathop{\overset{O}{\mathop{\overset{||}{\mathop{C}}\,}}\,}}\,-C{{H}_{3}}\xrightarrow{{{l}_{2}}/NaOH}\underset{\text{yellow ppt}\text{.}}{\mathop{\underset{'B'}{\mathop{C{{H}_{3}}}}\,}}\,\]\[+C{{H}_{3}}COONa+Nal+{{H}_{2}}O\] \[C{{H}_{3}}\underset{A}{\mathop{\overset{O}{\mathop{\overset{||}{\mathop{C}}\,}}\,}}\,C{{H}_{3}}\xrightarrow[\begin{smallmatrix} \text{(Clemmensen }\!\!'\!\!\text{ s} \\ \text{reduction)} \end{smallmatrix}]{Zn-Hg/HCl}\underset{\text{ }\!\!'\!\!\text{ C }\!\!'\!\!\text{ }\text{.}}{\mathop{\underset{\text{propane}}{\mathop{C{{H}_{3}}C{{H}_{2}}}}\,C{{H}_{3}}}}\,\]
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