MCQ
Compound $C_4H_8Cl_2$ $(A)$ on hydrolysis gives a compound $C_4H_8O$ $(B)$ which reacts with hydroxylamine and does not give any test with Tollen's reagent. What are $(A)$ and $(B)$ ?
  • A
    $1,1-$ Dichlorobutane and butanal
  • B
    $2,2-$ Dichlorobutane and butanal
  • C
    $1,1-$ Dichlorobutane and butanone
  • $2,2-$ Dichlorobutane and butanone

Answer

Correct option: D.
$2,2-$ Dichlorobutane and butanone
d
$\underset{\begin{smallmatrix} 
 2,2\,\,-\,Dichlorobu\tan e\,\,(A) \\ 
 [{{C}_{4}}{{H}_{8}}C{{l}_{2}}] 
\end{smallmatrix}}{\mathop{\begin{matrix}
   \begin{matrix}
   Cl\,\,  \\
   |\,\,  \\
\end{matrix}\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,  \\
   C{{H}_{3}}-C-C{{H}_{2}}-C{{H}_{3}}  \\
   |\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,  \\
   Cl\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,  \\
\end{matrix}}}\,$ $\xrightarrow[{hydrolysis}]{{aq\,\,KOH}}$ $\begin{array}{*{20}{c}}
  {\begin{array}{*{20}{c}}
  {\,\,\,\,OH\,\,\,\,} \\ 
  |\,\,\,\,\,\, 
\end{array}\,\,\,\,\,\,\,\,\,\,\,\,\,\,} \\ 
  {C{H_3} - C - C{H_2} - C{H_3}} \\ 
  {|\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,} \\ 
  {OH\,\,\,\,\,\,\,\,\,\,\,\,\,} 
\end{array}$ $\xrightarrow[{ - \,\,{H_2}O}]{}$ $\underset{\begin{smallmatrix} 
 \,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,Bu\tan one\,\,\,[B] \\ 
 [Ketone\,\,does\,\,not\,\,give\,\,tollen's\,\,Test] 
\end{smallmatrix}}{\mathop{\begin{matrix}
   O\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,  \\
   ||\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,  \\
   C{{H}_{3}}-C-C{{H}_{2}}-C{{H}_{3}}  \\
\end{matrix}}}\,$  $\xrightarrow[\begin{subarray}{l} 
  hydroxyl \\ 
  a\min e 
\end{subarray} ]{{{H_2}N - OH}}$ $\mathop {\begin{array}{*{20}{c}}
  {N - OH\,\,\,} \\ 
  {||\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,} \\ 
  {C{H_3} - C - C{H_2} - C{H_3}} 
\end{array}}\limits_{Oxime} $

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