A) \[C{{H}_{3}}-\overset{\begin{smallmatrix} H \\ | \end{smallmatrix}}{\mathop{\underset{\begin{smallmatrix} | \\ OH \end{smallmatrix}}{\mathop{C}}\,}}\,-\underset{\begin{smallmatrix} | \\ C{{H}_{3}} \end{smallmatrix}}{\mathop{C}}\,H-COOH\]
B) \[C{{H}_{3}}-\overset{\begin{smallmatrix} C{{H}_{3}} \\ | \end{smallmatrix}}{\mathop{\underset{\begin{smallmatrix} | \\ OH \end{smallmatrix}}{\mathop{C}}\,}}\,-COOH\]
C) \[C{{H}_{3}}-\overset{\begin{smallmatrix} C{{H}_{3}} \\ | \end{smallmatrix}}{\mathop{\underset{\begin{smallmatrix} | \\ OH \end{smallmatrix}}{\mathop{C}}\,}}\,-C{{H}_{2}}NH\]
D) \[C{{H}_{3}}-\underset{\begin{smallmatrix} | \\ C{{H}_{3}} \end{smallmatrix}}{\mathop{C}}\,N-CN\]
Correct Answer: C
Solution :
When acetone reacts with KCN/\[{{H}_{2}}S{{O}_{4}}\] then addition of HCN takes place and acetone cyanohydrin is formed. On the reduction of compound by \[LiAl{{H}_{4}},-CN\] group is reduced into \[-C{{H}_{2}}N{{H}_{2}}\] (primary amine) group. \[C{{H}_{3}}-\overset{\begin{smallmatrix} O \\ || \end{smallmatrix}}{\mathop{\underset{acetone}{\mathop{C}}\,}}\,-C{{H}_{3}}+HCN\] \[\xrightarrow{KCN/{{H}_{2}}S{{O}_{4}}}\,\,\,\,C{{H}_{3}}-\overset{\begin{smallmatrix} C{{H}_{3}} \\ | \end{smallmatrix}}{\mathop{\underset{\begin{smallmatrix} | \\ OH \end{smallmatrix}}{\mathop{C}}\,}}\,-CN\] acetone cyanohydrin \[\xrightarrow{LiAl{{H}_{4}}}C{{H}_{3}}-\overset{\begin{smallmatrix} C{{H}_{3}} \\ | \end{smallmatrix}}{\mathop{\underset{\begin{smallmatrix} | \\ OH \\ (B) \end{smallmatrix}}{\mathop{C}}\,}}\,-C{{H}_{2}}N{{H}_{2}}\] Note - Isocyanide gives secondary amine on reduction. \[RNC\xrightarrow[or\,\,{{H}_{2}},\,\,Ni]{LiAl{{H}_{4}}}\underset{\sec ondary\,\,a\min e}{\mathop{R-NH-C{{H}_{3}}}}\,\]
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