On the basis of the mechanism for the acid-catalyzed formation of diethyl ether from ethanol in Figure
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Overall Reaction: H2504 2CH,CH,OH CHCH,OCH,CH H20 Ethanol Diethyl ether Water Step 1: Proton transfer from the acid catalyst to the oxygen of the alcohol to produce an alkyloxonim ion fast CH:CH Ethyl alcohol Sulfuric acid Ethyloxonium ion Hydrogen sulfate ion Step 2: Nucleophilic attack by a molecule of alcohol on the alkyloxonium ion formed in step1 Ethyl alcohol Ethyloxonium ion Diethyloxonium ion Water Step 3: The product of step 2 is the conjugate acid of the dialkyl ether. It is deprotonated in the final step of the process to give the ether fast CH CH,O CH2CH3 Diethyloxonium ion Hydrogen sulfate ion Diethyl ether Sulfuric acid
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