Summary of Ch 6 Alkene Reactions

Alkene






























Alkyl halide
H and X added
Carbocation intermediate
o 1,2-shift is possible
Regioselective reaction
o Markovnikovs Rule: H from H-X adds
to the C of C=C with the most H.
Not a stereoselective reaction
o If a new chiral center is formed, both
configurations are produced.

Alcohol
H and OH added
Carbocation intermediate
o 1,2-shift is possible
Regioselective reaction
o Markovnikovs Rule: H adds to the C of
C=C with the most H.
Not a stereoselective reaction
o If a new chiral center is formed, both
configurations are produced

Alkyl dihalides
X and X added
Onium ion intermediate
o 1,2-shift is not possible
Not a regioselective reaction (2
nd
Br
-
attacks the
more substituted C of onium ion)
Stereoselective anti

Halohydrin
X and OH added
Onium ion intermediate
o 1,2-shift is not possible
Regioselective reaction (Br adds to the less
substituted C, OH attacks the more substituted
C of onium ion)
Stereoselective anti
Alkene
1) Hg(OAc)
2
, H
2
O
2) NaBH
4
/
-
OH

































Alcohol
H and OH added
Onium ion intermediate
o 1,2-shift is not possible
Regioselective Reaction
o Markovnikovs Rule: H adds to the C of
C=C with the most H.
Stereoselective anti

Alcohol
H and OH added
Regioselective reaction
o Non-Markovnikovs Rule: -H on C of
C=C with the least H, -OH on C of C=C
with most H.
Stereoselective syn

Vicinal Diols
OH and OH added
Not a regioselective reaction
Stereoselective syn

Carbonyl Compounds
Split the C=C in half, and make each C of the
C=C a carbonyl carbon

Alkane
H and H added
Not a regioselective reaction
Stereoselective - syn