Reactions of Alkenes
(Carey, Chap. 6 +)

Reaction Product Notes
carbocation intermediate
rearrangement possible
cyclic halonium ion,
no rearrangement
Br2 diagnostic for C=C
cyclic halonium ion,
no rearrangement
carbocation intermediate
rearrangement possible
synchronous add'n of
B & H,
no rearrangement
 
Chap. 15
concerted addition, 6 e-
cyclic transition state
epoxidation;
concerted addition

alkene cleavage;
useful for structure
elucidation

alkene cleavage;
useful for structure
elucidation
 
Chap. 9
addition, followed by
double E2 elimination
of vicinal dihalide;
prep. of alkynes
Chap. 10
allylic free radical;
resonance-stabilized
NBS = N-bromosuccinimide
Chap. 10
allylic carbocation;
resonance-stabilized
1,2-adduct major with
  "kinetic control"
1,4-adduct major with
  "thermodyn. control"
Chap. 10
allylic carbocation;
resonance-stabilized
1,2-adduct major with
  "kinetic control"
1,4-adduct major with
  "thermodyn. control"

schwartz@chem.fsu.edu