question_answer

An organic compound \[A,{{C}_{5}}{{H}_{8}}O;\]reacts with \[{{H}_{2}}O,N{{H}_{3}}\]and \[C{{H}_{3}}COOH\] as described below: A is:   [JEE Main Online Paper ( Held On 11 Apirl  2014 )

A) \[C{{H}_{3}}CH=\underset{\begin{smallmatrix}  | \\  C{{H}_{3}} \end{smallmatrix}}{\mathop{C}}\,-CHO\]

B) \[C{{H}_{2}}=CH\underset{\begin{smallmatrix}  | \\  C{{H}_{3}} \end{smallmatrix}}{\mathop{CH}}\,-CHO\]

C) \[C{{H}_{3}}-C{{H}_{2}}-\underset{\begin{smallmatrix}  | \\  C{{H}_{3}} \end{smallmatrix}}{\mathop{CH}}\,=C=O\]

D) \[C{{H}_{3}}-C{{H}_{2}}-\underset{\begin{smallmatrix}  || \\  C{{H}_{2}} \end{smallmatrix}}{\mathop{CH}}\,-\underset{\begin{smallmatrix}  | \\  H \end{smallmatrix}}{\mathop{C}}\,=O\]

Correct Answer: C

Solution :

                Given compound A is \[C{{H}_{3}}-C{{H}_{2}}-\underset{\begin{smallmatrix}  | \\  C{{H}_{3}} \end{smallmatrix}}{\mathop{C}}\,=C=O\] Reactions given are as following : \[C{{H}_{3}}-C{{H}_{2}}-\underset{\begin{smallmatrix}  | \\  C{{H}_{3}} \end{smallmatrix}}{\mathop{C}}\,=C=O\xrightarrow[{}]{N{{H}_{3}}}\] \[C{{H}_{3}}-C{{H}_{2}}-\underset{\begin{smallmatrix}  | \\  C{{H}_{3}} \end{smallmatrix}}{\mathop{CH}}\,=\overset{\begin{smallmatrix}  O \\  || \end{smallmatrix}}{\mathop{C}}\,-N{{H}_{2}}\] \[C{{H}_{3}}-C{{H}_{2}}-\underset{\begin{smallmatrix}  | \\  C{{H}_{3}} \end{smallmatrix}}{\mathop{C}}\,=C=O\xrightarrow[{}]{{{H}_{2}}O}\] \[C{{H}_{3}}-C{{H}_{2}}-\underset{\begin{smallmatrix}  | \\  C{{H}_{3}} \end{smallmatrix}}{\mathop{C}}\,-COOH\] \[C{{H}_{3}}-C{{H}_{2}}-\underset{\begin{smallmatrix}  | \\  C{{H}_{3}} \end{smallmatrix}}{\mathop{C}}\,=C=O\xrightarrow[{}]{C{{H}_{3}}COOH}\] \[C{{H}_{3}}-CH-\underset{\begin{smallmatrix}  | \\  C{{H}_{3}} \end{smallmatrix}}{\mathop{CH}}\,-\overset{\begin{smallmatrix}  O \\  || \end{smallmatrix}}{\mathop{C}}\,-O-\overset{\begin{smallmatrix}  O \\  || \end{smallmatrix}}{\mathop{C}}\,-C{{H}_{3}}\]