A) cis and trans isomers of 2, 3-dimethyl-2-butene
B) 3, 3-dimethyl-1-butene
C) 2, 3-dimethyl-2-butene
D) 2, 3-dimethyl-1-butene
Correct Answer: C
Solution :
\[\underset{\,\,\,\,\,OH\,\,\,\,\,C{{H}_{3}}}{\mathop{\underset{|\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,|\,\,}{\mathop{\overset{\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,C{{H}_{3}}}{\mathop{\overset{\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,|}{\mathop{C{{H}_{3}}-CH-C-C{{H}_{3}}}}\,}}\,}}\,}}\,\xrightarrow{{{H}_{2}}S{{O}_{4}}}\]\[\underset{{{\text{2}}^{\text{o}}}\text{carbonium}\,\text{ion}\,\,\,\,\,\,\,\,\,\,}{\mathop{C{{H}_{3}}-\overset{+}{\mathop{C}}\,H-\,\underset{\underset{C{{H}_{3}}\,\,\,\,\,}{\mathop{|\,\,\,\,\,\,\,\,\,\,\,\,\,\,}}\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,}{\overset{\overset{C{{H}_{3}}\,\,\,\,}{\mathop{|\,\,\,\,\,\,\,\,\,\,\,\,}}\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,}{\mathop{C\,\,-\,C{{H}_{3}}+O{{H}^{-}}\,}}}\,\underset{\text{Rearrangement}}{\mathop{\xrightarrow{\text{Methyl shift}}}}\,}}\,\] \[\underset{\begin{smallmatrix} \text{2,3}-\text{dimethyl}-\text{2}-\text{Butene} \\ [\text{Most}\,\text{synnetrialStructure}] \end{smallmatrix}}{\mathop{C{{H}_{3}}-\overset{\,\,\overset{C{{H}_{3}}}{\mathop{|\,\,\,\,\,\,\,\,\,}}\,}{\mathop{C=\,}}\,\overset{\overset{C{{H}_{3}}}{\mathop{|\,\,\,\,\,\,\,\,\,}}\,\,\,\,\,\,\,\,\,\,}{\mathop{C-C{{H}_{3}}}}\,}}\,\xleftarrow[-{{H}^{+}}]{}\]\[\underset{{{\text{3}}^{\text{o}}}\text{Carbonium}\,\text{ion}\,\left( \text{More}\,\text{stable} \right)}{\mathop{C{{H}_{3}}-\overset{\overset{C{{H}_{3}}}{\mathop{|\,\,\,\,\,\,\,}}\,\,\,}{\mathop{CH-}}\,\overset{\overset{C{{H}_{3}}}{\mathop{|\,\,\,\,\,\,\,}}\,}{\mathop{\underset{+\,\,\,}{\mathop{C-}}\,}}\,C{{H}_{3}}}}\,\,\]
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