Engineering
Chemistry
Chemical Reactions of Alcohols
Chemical reactions of ether
Question

Can you explain why is bimolecular dehydran not appropriate for the preparation of ethyl methyl ether ?

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Solution

"Bimolecular dehydration" is a way of preparing diethyl ether from the dehydrating action of concentrated sulfuric acid on ethanol. First step is protonation of one alcohol molecule (ethanol) by conc. H2SO4 and in second step nucleophilic attack by second ethanol molecule leading to loss of water molecule. abstracts a hydrogen from one ethanol and a hydroxyl (the – OH group) of a neighbor. In third step loss of proton takes place and symmetrical ether is formed.
So this method works only with symmetrical ethers: di[alkyl] ethers. Methyl Ethyl ether is better prepared from Sodium ethoxide and methanol or Sodium methoxide and ethanol.

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