Alcohols Phenols and EthershardMCQ MULTIPLE

Consider the preparation of ethers via the acid-catalyzed intermolecular dehydration of alcohols. WhAlcohols Phenols and Ethers Chemistry Question

Question

Consider the preparation of ethers via the acid-catalyzed intermolecular dehydration of alcohols. Which of the following mechanistic statements are true?

Answer: A,B,D

💡 Solution & Explanation

Step 1 is protonation (fast). Step 2 is the $S_N2$ attack of a neutral alcohol on the oxonium ion (slow, rate-determining) to form the ether and release water. Secondary and tertiary alcohols suffer from severe steric hindrance, causing elimination ($E1$/$E2$) to dominate over substitution, forming alkenes (Statement D). Statement C is false; mixing two different alcohols yields a complex mixture of three different ethers, making it synthetically useless for unsymmetrical ethers.

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