1 (593)

Prévia do material em texto

Solutions for Condensations and Alpha Substitutions of Carbonyl Compounds
C
OMe
HO
O
CH3CH3
O
OMe
plus one other 
resonance form
(dehydration)
– HO
from previous page73 (c) continued
The negative charge in this structure
is stabilized by resonance with the 
carbonyl.
two rapid
proton transfers
+
plus one other
resonance form
two rapid
proton transfers
plus one other
resonance form
two rapid
proton transfers
N
H
O
H
O
C
N
H
N
O
H
H
O
N
OH
H
N H
OH
O
H
N
C
H
O
C
OH
O
OH
H
H
H
O
O
H
O H
O
H
H
H
(d)
H H
– H2O
H3O+
H2O
H3O+
H3O+
H3O+
H2O
H2O
H2O
enol 
tautomer
mechanism continued on next page
588