Reactions of Alcohols - I
(Carey, Chap. 4 +)

Reaction Product Notes
Prep. of alkoxides;
conjugate bases of
   pKa 16-18 acids
SN1 subst. (2o & 3o);
carbocation intermediate
rearrangement possible
rel. rates: HBr > HCl; 3o > 2o
SN2 subst.;
no rearrangement
rel. rates: 1o > 2o
SN2 subst.;
no rearrangement
rel. rates: 1o > 2o
Chap. 8
sulfonate esters
good leaving groups,
(like halide)
Chap. 5
E1 elimination;
carbocation intermediate
rearrangement possible
Chap. 10
allylic carbocation
resonance stabilized

schwartz@chem.fsu.edu