Question

Give the mechanism of the following reaction:

\[\ce{CH3CH2OH ->[H2SO4][413 K] CH3CH2-O-CH2CH3 + H2O}\]

Answer 1

\[\ce{CH3CH2OH ->[H2SO4][413 K] \underset{Diethylether}{CH3CH2-O-CH2CH3} + H2O}\]

Mechanism: The formation of ether is a nucleophilic bimolecular reaction S_N2 involving the attack of alcohol molecules on protonated alcohol as below:

(1) \[\ce{CH3CH2 - \underset{\bullet\bullet}{\overset{\bullet\bullet}{O}} - H + H+ -> CH3CH2 -^+ \underset{\bullet\bullet}{\overset{\ce{H}}{\overset{\bullet\bullet}{O}}} - H}\]

(2) 

(3) \[\begin{array}{cc}
\ce{CH3CH2-\overset{+}{O}-CH2CH3 -> CH3CH2-O-CH2CH3 + H^+}\\
|\phantom{..................................}\\
\ce{H}\phantom{..................................}
\end{array}\]

\[\ce{H^+ + HSO^Θ_4 -> H2SO4}\]