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Question 69 of 76

Q.Write any one method of preparation for diethyl ether.

Puducherry TnboardTamil Nadu HSC (DGE) Board 2022Subjective· 3mImportance★★★★★
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Diethyl ether is prepared industrially/in the lab by heating excess ethanol with concentrated sulphuric acid at about 413 K, which dehydrates two molecules of ethanol intermolecularly to give the ether.

Method: Acid-catalysed dehydration of ethanol (Williamson's continuous process).

When excess ethanol is heated with concentrated sulphuric acid at about 413 K (140 degC), two molecules of ethanol undergo intermolecular dehydration (loss of one water molecule between them) to give diethyl ether:

C2H5−OH+H−O−C2H5→413 Kconc. H2SO4C2H5−O−C2H5+H2OC_2H_5-OH + H-O-C_2H_5 \xrightarrow[413\,K]{conc.\,H_2SO_4} C_2H_5-O-C_2H_5 + H_2O

Mechanism (briefly):

  1. Concentrated H2SO4H_2SO_4 protonates the −OH-OH oxygen of one ethanol molecule, converting it into a good leaving group (C2H5−O+H2C_2H_5-\overset{+}{O}H_2, a protonated alcohol/oxonium ion).
  2. A second, un-protonated ethanol molecule then acts as a nucleophile, attacking the electrophilic carbon of the protonated alcohol (or its oxygen attacking via an SN2S_N2-type displacement of water).
  3. Loss of water and then loss of a proton (deprotonation of the resulting protonated ether) gives the neutral ether, C2H5−O−C2H5C_2H_5-O-C_2H_5, regenerating the H2SO4H_2SO_4 catalyst. …

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