6) The π bond of an alkene can act as a base:
CC + H A + A−
Alkene Carbocation
+
Strong acid Weak base
CC
R
R
H
The π bond breaks
This bond breaks This bond is formed
i) The π bond of the double bond and the bond between the proton of the acid and
its conjugate base are broken; a bond between a carbon of the alkene and the
proton is formed.
ii) A carbocation is formed.
3.13 A MECHANISM FOR AN ORGANIC REACTION
1.
HO +
H
H 3 C C + H Cl −
CH 3
CH 3
OH +
tert-Butyl alcohol Conc. HCl
(soluble in H 2 O)
H 3 C C
CH 3
CH 3
Cl +2 H 2 O
tert-Butyl chloride
(
H 2 O
insoluble in H 2 O)
