Question
What type of mechanism is followed by dehydration of alcohol to form ether?
What type of mechanism is followed by dehydration of alcohol to form ether?
B. Nucleophilic substitution bimolecular reaction
The dehydration of alcohols to form ethers is an acid-catalyzed reaction that proceeds via an S_N2 mechanism. Step 1: Protonation of the alcohol to form an oxonium ion. R-OH + H^+ R-OH_2^+ Step 2: Nucleophilic attack of an unprotonated alcohol molecule on the protonated alcohol. This is a bimolecular nucleophilic substitution (S_N2) reaction where water acts as the leaving group. R-OH + R-OH_2^+ R-O^+(H)-R + H_2O Step 3: Loss of a proton to yield the ether. R-O^+(H)-R R-O-R + H^+ Since the rate-determining step involves two molecules (the alcohol acting as a nucleophile and the protonated alcohol acting as the substrate), the mechanism is a nucleophilic substitution bimolecular reaction.
Related: Chemistry — Alcohols Phenols and Ethers · All PYQ Banks