A) \[C{{H}_{3}}-\underset{H}{\mathop{\underset{|}{\mathop{\overset{C{{H}_{3}}}{\mathop{\overset{|}{\mathop{C}}\,}}\,}}\,}}\,-C{{H}_{2}}OC{{H}_{3}}\]
B) \[C{{H}_{3}}-\underset{OC{{H}_{3}}}{\mathop{\underset{|}{\mathop{CH}}\,}}\,-C{{H}_{2}}C{{H}_{3}}\]
C) \[C{{H}_{3}}-\overset{C{{H}_{3}}}{\mathop{\overset{|}{\mathop{C}}\,}}\,=C{{H}_{2}}\]
D) \[C{{H}_{3}}-\underset{OC{{H}_{3}}}{\mathop{\underset{|}{\mathop{\overset{C{{H}_{3}}}{\mathop{\overset{|}{\mathop{C}}\,}}\,}}\,}}\,-C{{H}_{3}}\]
Correct Answer: D
Solution :
The reaction is an example of nucleophilic substitution reaction. The mechanism is as follows: \[C{{H}_{3}}-\overset{C{{H}_{3}}}{\mathop{\overset{|}{\mathop{\underset{H}{\mathop{\underset{|}{\mathop{C}}\,}}\,}}\,}}\,-C{{H}_{2}}-Br\xrightarrow{-B{{r}^{-}}}\] \[\underset{{{1}^{o}}\,carbocation}{\mathop{C{{H}_{3}}-\underset{H}{\mathop{\underset{|}{\mathop{\overset{C{{H}_{3}}}{\mathop{\overset{|}{\mathop{C}}\,}}\,}}\,}}\,-\overset{+}{\mathop{C}}\,{{H}_{2}}}}\,\] \[\underset{{{3}^{o}}\,carbocation}{\mathop{\xrightarrow[(hydride\,shift)]{\operatorname{Re}arangement}C{{H}_{3}}-\overset{C{{H}_{3}}}{\mathop{\overset{|}{\mathop{{{C}^{+}}}}\,}}\,-C{{H}_{3}}\xrightarrow{C{{H}_{3}}{{O}^{-}}}}}\,\] \[\underset{2-methoxypropane}{\mathop{\xrightarrow{{}}CH_{3}^{1}{{-}^{2}}\overset{C{{H}_{3}}}{\mathop{\overset{|}{\mathop{\underset{OC{{H}_{3}}}{\mathop{\underset{|}{\mathop{C}}\,}}\,}}\,}}\,{{-}^{3}}C{{H}_{3}}}}\,\]
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