question_answer

An alkene of molecular formula \[{{C}_{9}}{{H}_{18}}\] on ozonolysis gives 2, 2 dimethyl propanal & 2-butanon, then the alkene is [Kerala CET 2005]

A)                 2, 2, 4-trimethyl ?3-hexene

B)                 2, 2, 6-trimethyl-3-hexene

C)                 2, 3, 4-trimethyl-2-hexene

D)                 2, 2, 4-trimethyl-2-hexene

E)                 2, 2dimethyl-2-heptene

Correct Answer: A

Solution :

           \[\underset{2,2\text{ dimethyl propanal }}{\mathop{{{C}_{9}}{{H}_{18}}+{{O}_{3}}\to {{H}_{3}}C\underset{C{{H}_{3}}\,\,\,\,\,\,}{\mathop{\underset{|\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,}{\mathop{\overset{C{{H}_{3}}\,\,\,\,\,\,}{\mathop{\overset{|\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,}{\mathop{-C-CHO}}\,}}\,}}\,}}\,+\underset{2-\text{butanone}}{\mathop{C{{H}_{3}}C{{H}_{2}}COC{{H}_{3}}}}\,}}\,\]                    On the basis of product formation, it would be alkene                    \[\underset{2,2,\,4-\text{trimethyl-3-hexene}}{\mathop{\overset{\,\,\,\,\,\,\,C{{H}_{3}}}{\mathop{\overset{|}{\mathop{\underset{\,\,\,\,\,\,C{{H}_{3}}}{\mathop{\underset{|}{\mathop{C{{H}_{3}}-C-HC}}\,}}\,}}\,}}\,=\overset{C{{H}_{3}}}{\mathop{\overset{|\,\,\,\,\,\,\,}{\mathop{C-}}\,}}\,C{{H}_{2}}C{{H}_{3}}}}\,\]            \[\overset{\,\,\,\,\,\,\,C{{H}_{3}}}{\mathop{\overset{|}{\mathop{\underset{\,\,\,\,\,\,C{{H}_{3}}}{\mathop{\underset{|}{\mathop{C{{H}_{3}}-C-HC}}\,}}\,}}\,}}\,=\overset{C{{H}_{3}}}{\mathop{\overset{|\,\,\,\,\,\,\,}{\mathop{C-}}\,}}\,C{{H}_{2}}C{{H}_{3}}\xrightarrow{{{O}_{3}}}\]   \[\to \overset{C{{H}_{3}}\,\,\,}{\mathop{\overset{|\,\,\,\,\,\,\,\,\,\,\,\,\,}{\mathop{\underset{C{{H}_{3}}\,\,\,}{\mathop{\underset{|\,\,\,\,\,\,\,\,\,\,\,\,\,}{\mathop{C{{H}_{3}}C}}\,}}\,}}\,}}\,-CHO+C{{H}_{3}}C-\overset{O\,\,\,\,\,\,\,\,\,\,\,\,\,\,}{\mathop{\overset{|\,|\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,}{\mathop{C{{H}_{2}}C{{H}_{3}}}}\,}}\,\]