question_answer

Identify the product of the following reaction : \[\underset{{}}{\mathop{C{{H}_{3}}-\underset{\begin{smallmatrix}  | \\  \,C{{H}_{3}} \end{smallmatrix}}{\overset{\begin{smallmatrix}  C{{H}_{3}} \\  | \end{smallmatrix}}{\mathop{C}}}\,-C{{H}_{2}}-Br\xrightarrow[\Delta ]{EtOH}}}\,\]

Answer:

                In presence of a weak nucleophile such as ethanol, neopentyl bromide ionizes to form first a \[1{}^\circ \] carbocation which rearranges to form the more stable \[3{}^\circ \]carbocation. This is then attacked by weak nucleophile ethanol followed by loss of a proton to yield ethyl tert-pentyl ether.