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Dehydration of Alcohols

Dehydration of alcohols involves treating an alcohol with a strong acid, which results in the removal of a water molecule. For secondary alcohols, this dehydration reaction can occur through either an E1 or E2 mechanism. In an E1 mechanism, proton transfer forms an oxonium ion intermediate followed by cleavage of the C-O bond to form a carbocation. In an E2 mechanism, proton transfer and loss of water occur simultaneously without formation of a carbocation intermediate.

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108 views3 pages

Dehydration of Alcohols

Dehydration of alcohols involves treating an alcohol with a strong acid, which results in the removal of a water molecule. For secondary alcohols, this dehydration reaction can occur through either an E1 or E2 mechanism. In an E1 mechanism, proton transfer forms an oxonium ion intermediate followed by cleavage of the C-O bond to form a carbocation. In an E2 mechanism, proton transfer and loss of water occur simultaneously without formation of a carbocation intermediate.

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Aina Syafiqah
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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.

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