Reactions of carbonyl groups
• Nucleophilic addition
• Nucleophilic substitution to form C=Nu
• Nucleophilic acyl substitution
– Of a leaving group in an acid or derivative
• Alpha-substitution from the enol or enolate
– Alkylation
– Carbonyl condensation
Nucleophilic addition
O
R
C
OH
H Nu
O
H2O
HO OH
R C R
R
general form
Nu
O
PhMgBr
OH
H3C C CH3
Nucleophilic substitution
to form C=Nu
O
O
R
C
NH
Nu
H2Nu
R
NH3
R
general form
C
R
O
HN(CH 3)2
N(CH3)2
Nucleophilic acyl substitution
R
O
Nu
O
C
or HNu
C
X
R
O
Nu
NH3
O
Cl
general form
O
NH2
O
H+
OH
CH3OH
OCH3
O
Alpha-substitution R
C
O
E
H
CR2
R
C
E
CR2
general form
O
O
NaOCH2CH3
H
CH3CH2O
RX
O
O
H
NaOH
R
CH3CH2O
OH
O