|Chapter 15: Alcohols, Diols and Thiols|
An acid/base reaction. Protonation of the alcoholic oxygen to make a better leaving group. This step is very fast and reversible. The lone pairs on the oxygen make it a Lewis base.
Cleavage of the C-O bond allows the loss of the good leaving group, a neutral water molecule, to give a carbocation intermediate. This is the rate determining step (bond breaking is endothermic)
An acid/base reaction. Deprotonation by a base (a water molecule) from a C atom adjacent to the carbocation center leads to the creation of the C=C
|© Dr. Ian Hunt, Department of Chemistry, University of Calgary|