How to convert ethyl alcohol to diethyl ether
Answers
Answered by
14
There are two ways to make diethyl ether (CH3CH2OCH2CH3) from ethanol (CH3CH2OH). The first and most straightforward is to mix ethanol with a strong acid, typically sulfuric acid, H2SO4. The acid dissociates in the aqueous like environment producing hydronium, H3O+. A hydrogen ion protonates the oxygen atom of ethanol, giving the ethanol molecule a positive charge:
CH3CH2OH + H3O+ → CH3CH2OH2+ + H2O
The nucleophilic oxygen atom of unprotonated ethanol then displaces a water molecule from the protonated ethanol molecule, producing water, a hydrogen ion and diethyl ether.
CH3CH2OH2+ + CH3CH2OH → H2O + H+ + CH3CH2OCH2CH3
The second, as has been pointed out, is the Williamson ether synthesis, though I would like to offer a variation of the them.
First, I would convert ethanol to ethyl bromide. One method for this is to treat ethanol with concentrated sulfuric acid and then add to potassium bromide. This will yield ethyl bromide (CH3CH2-Br).
Next, treat absolute ethanol (100%, aka 200 proof) with sodium metal to generate the alkoxide (CH3CH2-ONa) followed by reaction with ethyl bromide to yield diethyl ether.
CH3CH2OH + Na → CH3CH2-ONa
CH3CH2-ONa + CH3CH2-Br → CH3CH2OCH2CH3
CH3CH2OH + H3O+ → CH3CH2OH2+ + H2O
The nucleophilic oxygen atom of unprotonated ethanol then displaces a water molecule from the protonated ethanol molecule, producing water, a hydrogen ion and diethyl ether.
CH3CH2OH2+ + CH3CH2OH → H2O + H+ + CH3CH2OCH2CH3
The second, as has been pointed out, is the Williamson ether synthesis, though I would like to offer a variation of the them.
First, I would convert ethanol to ethyl bromide. One method for this is to treat ethanol with concentrated sulfuric acid and then add to potassium bromide. This will yield ethyl bromide (CH3CH2-Br).
Next, treat absolute ethanol (100%, aka 200 proof) with sodium metal to generate the alkoxide (CH3CH2-ONa) followed by reaction with ethyl bromide to yield diethyl ether.
CH3CH2OH + Na → CH3CH2-ONa
CH3CH2-ONa + CH3CH2-Br → CH3CH2OCH2CH3
Answered by
30
Answer:
Diethyl ether can be obtained by heating ethyl alcohol in concentrated sulfuric acid.
Explanation:
Heating alcohols with concentrated sulfuric acid or in phosphoric acid results in condensation of of two alcohol molecules along with removal of water molecule to produce an ether.
Similar questions