Formation of symmetrical ether or dehydration of primary alcohol?

Asked Jan 16 '17 at 08:50

Active Apr 01 '17 at 02:21

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My textbook gives the formation of diethyl ether from dehydration of ethyl alcohol:

$\ce{\underset{\text{ethyl alcohol}}{2C2H5-OH} ->[\text{conc.} H2SO4][413~K] \underset{\text{diethyl ether}}{C2H5-O-C2H5} + H2O}$

In the reaction where it is said that concentrated $\ce{H2SO4}$ at temperature $413~\mathrm K$ is used as a catalyst, will the primary alcohol not dehydrate to form alkene?

Concentrated sulfuric acid is a strong dehydrating agent, and is used as $95~\%$ concentrated when dehydrating primary alcohol. So will the alcohol dehydrate or will the diethyl ether be formed?

edited Apr 01 '17 at 02:21

Melanie Shebel

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asked Jan 16 '17 at 08:50

Ishaan

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When forming an alkene this way you have a carbocation intermediate. This isn't very stable on a terminal carbon, so that pathway is not very favorable. – airhuff Jan 16 '17 at 09:11
Still, if we push harder, it will dehydrate. – Ivan Neretin Jan 16 '17 at 10:19
Indeed, $413~\mathrm K$ ($140~^\circ \mathrm C$) is used for this reaction while $453~\mathrm K$ ($180~^\circ \mathrm C$) is used for making ethene from ethanol. We might have to resort to the concept of thermodynamic and kinetic control. – DHMO Jan 16 '17 at 12:52
Related: http://chemistry.stackexchange.com/questions/41836/reactions-of-alcohol-with-sulfuric-acid – Nilay Ghosh Jan 16 '17 at 13:27

Formation of symmetrical ether or dehydration of primary alcohol?

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