EXPERIMENT 2

Beginning with the departure of a departing group (shown by the letter "X" in the overall figure above),
an E1 elimination results in the production of a carbocation intermediate (step 1). Two electrons are
sent down to occupy the empty p orbital of the carbocation after the removal of a proton from a nearby
carbon in step two, creating a new p bond. The leaving group or another basic species in solution could
serve as the basis in this step.

When the leaving group is linked to a main carbon, E1 elimination does not take place unless the
carbon is in the allylic or benzylic position. Remember that a primary carbocation is a highly unstable
and unlikely reaction intermediate unless it is stabilized by resonance.

Nevertheless, E1 eliminations can be place at secondary carbons. When cyclohexanol is heated with
phosphoric acid in a catalytic amount, the end product is cyclohexene due to the dehydration
(elimination) of water. The phosphoric acid's job is to protonate the alcohol (see "step a" below), which
turns it into a useful leaving group.