synthesis and reactions of esters

r-cooh to r-cooch3

acid base with an sn2 (new)

:-ch2-N+≡N

r-cocl to r-coor

r-oh and pyridine

review rxn

ester from and acid chloride rxns of alcohols

r-cooh to r-coor

r-oh/h+ (cat.)
benzene

h2o scavenger

review rxn fischer esterification (review) addn/elim rxn of alcohols

anhydrides to ester

r-oh/h+ cat or r-o-
addn/elim (new)

can occur with weak or strong nu:

practice mechanism

ester to ester

r-oh/h+ cat or r-o-

trans esterification (new)

can occur with a weak or strong nu
(e.g. an alcohol or an alkoxide)

ester to cooh

saponification

hydrolysis under basic conditions (new)

1) koh/ch3oh
2) acid water

ester to cooh

water and acid

hydrolysis under acidic conditions (review)

reverse of fischer esterification

ester to amide

no mechanism

addn/elim mechanism

with R-NH2

ester to alcohol

1) 2eq R-mgbr

2) acid water

addn/elim review

ester and nabh4/meoh

no rxn

nabh4 is weak reducing

ester and lialh4

alcohol

acid water

ester to aldehyde

1) dibal

2) acid water

addn/elim