The formation of ethers during acidic dehydration involves a nucleophilic bimolecular (SN₂) reaction, where the alcohol molecule attacks a protonated alcohol. This method is suitable for preparing ethers with primary alkyl groups, requiring unhindered alkyl groups and low temperatures.
Describe the mechanism of nucleophilic bimolecular (SN₂) reaction involved in the formation of ethers during acidic dehydration of alcohols, and under what conditions is this method suitable for preparing ethers?
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In the nucleophilic bimolecular (SN₂) mechanism during acidic dehydration of alcohols, a protonated alcohol reacts with another alcohol molecule. The nucleophile, an oxygen atom from the second alcohol, attacks the protonated carbon, leading to the expulsion of water. This concerted process forms an ether and regenerates the acidic catalyst. This method is suitable for preparing ethers under mild acidic conditions, such as using sulfuric acid or hydrochloric acid, and is particularly effective with primary alcohols. However, steric hindrance and the presence of more substituted alcohols may favor other pathways, such as E¹ or E² reactions, yielding alkenes.