question_answer

A compound \[A\to {{C}_{5}}{{H}_{10}}C{{l}_{2}}\] on hydrolysis gives \[{{C}_{5}}{{H}_{10}}O\] which reacts with \[N{{H}_{2}}OH\], forms iodoform but does not give fehling test. \[A\] is              [DPMT 2005]

A)                 \[C{{H}_{3}}\underset{Cl}{\mathop{\underset{|}{\mathop{\overset{Cl}{\mathop{\overset{|}{\mathop{-C-}}\,}}\,}}\,}}\,C{{H}_{2}}-C{{H}_{2}}-C{{H}_{3}}\]

B)                \[C{{H}_{3}}C{{H}_{2}}\underset{Cl}{\mathop{\underset{|}{\mathop{\overset{Cl}{\mathop{\overset{|}{\mathop{-C-}}\,}}\,}}\,}}\,C{{H}_{2}}C{{H}_{3}}\]

C) \[C{{H}_{3}}C{{H}_{2}}C{{H}_{2}}C{{H}_{2}}\underset{Cl\,\,}{\mathop{\underset{|\,\,\,\,\,\,}{\mathop{\overset{Cl\,}{\mathop{\overset{|\,\,\,\,\,}{\mathop{CH}}\,}}\,}}\,}}\,\]

D)                 \[C{{H}_{3}}\overset{Cl}{\mathop{\overset{|}{\mathop{-CH}}\,}}\,\overset{Cl}{\mathop{\overset{|}{\mathop{-CH}}\,}}\,-C{{H}_{2}}-C{{H}_{3}}\]