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Q. The compounds that will give an isomer of 2,2- dimethylpropane on catalytic hydrogenation are (1) $ C{{H}_{3}}CH=\underset{\begin{smallmatrix} | \\ C{{H}_{3}} \end{smallmatrix}}{\mathop{C}}\,-C{{H}_{3}} $ (2) $ C{{H}_{3}}CH=CHC{{H}_{3}} $ (3) $ C{{H}_{3}}CH=CHC{{H}_{2}}C{{H}_{3}} $ (4) $ C{{H}_{3}}\underset{\begin{smallmatrix} | \\ C{{H}_{3}} \end{smallmatrix}}{\mathop{C}}\,=\underset{\begin{smallmatrix} | \\ C{{H}_{3}} \end{smallmatrix}}{\mathop{C}}\,-C{{H}_{3}} $

AMUAMU 1999

Solution:

: Formula of 2, 2-dimethyl propane is $ {{H}_{3}}C-\underset{\begin{smallmatrix} | \\ C{{H}_{3}} \end{smallmatrix}}{\overset{\begin{smallmatrix} C{{H}_{3}} \\ | \end{smallmatrix}}{\mathop{C}}}\,-C{{H}_{3}} $ $ C{{H}_{3}}CH=\underset{\begin{smallmatrix} | \\ C{{H}_{3}} \end{smallmatrix}}{\mathop{C}}\,-C{{H}_{3}} $ on catalytic hydrogenation will give $ C{{H}_{3}}CH-\underset{\begin{smallmatrix} | \\ C{{H}_{3}} \end{smallmatrix}}{\mathop{CH}}\,-C{{H}_{3}} $ which is an isomer of 2, 2-dimethylpropane. Also, $ C{{H}_{3}}CH=CHC{{H}_{2}}C{{H}_{3}} $ will give an isomer of 2, 2-dimethyl propane on hydrogenation.