DEHYDRATION OF ALCOHOLS

 Dehydration is carried out by the treatment of an alcohol with a strong acid.

example:

A Mechanism for Dehydration of Secondary Alcohols:

An E1 Reaction

1) Proton transfer from H₃O⁺ to the OH− group to form oxonium ion. This step convert
from OH−, a poor leaving group into H2O, a better leaving group.
2) C–O bonds breaks, gives a secondary carbocation and H2O.

3) Proton transfer from the carbon adjacent to the C + to H2O. the sigma electron of a
C–H bond become the pi electrons of the C=C.

A Mechanism for Dehydration of Secondary Alcohols:

An E2 Reaction

1) Proton transfer from H₃O⁺ to the OH− group to form oxonium ion.
2) Simultaneous proton transfer to solvent and loss H 2O gives the alkene.