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Identify product $D$ in the following reaction sequence

$\begin{matrix}
   \begin{matrix}
   \,\,\,\,\,C{{H}_{3}}  \\
   |  \\
\end{matrix}\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,  \\
   C{{H}_{3}}-C-C{{H}_{2}}C{{H}_{2}}OH  \\
   |\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,  \\
   C{{H}_{3}}\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,  \\
\end{matrix}$ $\xrightarrow[{{H_2}O,heat}]{{{K_2}C{r_2}{O_7};{H_2}S{O_4}}}A$ $\xrightarrow{{SOC{l_2}}}B\xrightarrow[{(2{\kern 1pt} mole)}]{{{{(C{H_3})}_2}NH}}C$ $\xrightarrow[{2.{\kern 1pt} {H_2}O}]{{\begin{array}{*{20}{c}}
  {1.{\kern 1pt} LiAl{H_4}} \\ 
  {diethyl{\kern 1pt} {\kern 1pt} ether} 
\end{array}}}D$

  • A$\begin{matrix}
       C{{H}_{3}}\,\,\,\,\,\,\,  \\
       |\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,  \\
       C{{H}_{3}}\,C\,C{{H}_{2}}C\equiv N  \\
       |\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,  \\
       C{{H}_{3}}\,\,\,\,\,\,\,\,\,\,  \\
    \end{matrix}$
  • B$\begin{array}{*{20}{c}}
      {\begin{array}{*{20}{c}}
      {\,\,\,\,\,\,\,C{H_3}\,\,\,\,} \\ 
      {|\,\,\,\,} 
    \end{array}\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,} \\ 
      {C{H_3}{\mkern 1mu} C{\mkern 1mu} C{H_2}C{H_2}N{{(C{H_3})}_2}} \\ 
      {|\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,} \\ 
      {C{H_{3\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,}}\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,} 
    \end{array}$
  • C$\begin{matrix}
       \,\,\,C{{H}_{3}}\,\,\,N{{(C{{H}_{3}})}_{2}}  \\
       |\,\,\,\,\,\,\,\,\,\,\,\,\,|\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,  \\
       C{{H}_{3}}\,C\,C{{H}_{2}}CHN{{(C{{H}_{3}})}_{2}}  \\
       |\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,  \\
       C{{H}_{3}}\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,  \\
    \end{matrix}$
  • D$\begin{array}{*{20}{c}}
      {\begin{array}{*{20}{c}}
      {C{H_{3\,\,\,\,}}\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,} \\ 
      {|\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,} 
    \end{array}} \\ 
      {C{H_3}CC{H_2}CHN{{(C{H_3})}_2}} \\ 
      {|\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,|\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,} \\ 
      {C{H_3}\,\,\,\,\,\,\,\,OH\,\,\,\,\,\,\,\,\,\,\,} 
    \end{array}$
Difficult
art

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