Heating of $\left[\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{CH}\left(\mathrm{CH}_{3}ight)…

Heating of $\left[\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{CH}\left(\mathrm{CH}_{3}ight) \mathrm{N}^{+}\left(\mathrm{CH}_{3}ight)_{3}ight] \mathrm{OH}^{-}$produces
  1. $\mathrm{CH}_{2}=\mathrm{CH}_{2}$.
  2. $\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{CH}=\mathrm{CH}_{2}$
  3. $\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}=\mathrm{CHCH}_{3}$
  4. $\mathrm{CH}_{2}=\mathrm{CHCH}_{2} \mathrm{CH}=\mathrm{CH}_{2}$

Solution

In Hofmann elimination, a less substituted alkene is formed as a result of the loss of more acidic BH (which follows the trend $1^{\circ}>2^{\circ}>3^{\circ}$ ). The reaction is
$$
\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{CH}\left(\mathrm{CH}_{3}ight) \mathrm{N}^{+}\left(\mathrm{CH}_{3}ight)_{3} \longrightarrow \mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{CH}=\mathrm{CH}_{2}
$$ ^

Asked in: JEE-TOPICTESTS-CHEMISTRY

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