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Solutions for Condensations and Alpha Substitutions of Carbonyl Compounds
C H
O
Ph
O
O
H
O
Ph
Ph3P CHCH3
EtO OEt
O O
NaOH
OO
OEtEtO
PhCH CHCH3
OH
O
H
O CH3
PhO
Br
H3O+
EtO OEt
O O
+
(e)
+
(d)
(b) reagents: Br2, PBr3, 
 followed by H2O
(c)(a) reagents: Br2, HOAc
69
70 In the products, the wavy lines indicate the bonds that must be made by alkylation, before hydrolysis 
and decarboxylation produce the substituted acetic acid.
(a)
(b) 1) NaOEt
2) CH3CH2Br
∆
CO2 + 2 EtOH +
1) NaOEt
2)
EtO OEt
O O OO
OEtEtO
CH2Ph
H3O+
CH2Ph
OH
O1) NaOEt
2) PhCH2Br ∆
+ CO2 + 2 EtOH
Ph3P O
(f)
O
Et2NH
HA
N
Et Et
+
N
CH3O
Cl
H2O N
CH3OO
An enamine avoids 
self-condensation. 
Any 2° amine could 
be used to form the 
enamine.
EtO OEt
O O
OO
OEtEtO
H3O+ COOH1) 2 NaOEt
2) Br(CH2)5Br ∆
+ CO2 + 2 EtOH(c)
reagents: excess I2 (or Br2 or Cl2), 
NaOH
EtO
O O OO
EtO CH2Br EtO
O O H3O+
O
71 In the products, the wavy lines indicate the bonds that must be made by alkylation, before hydrolysis 
and decarboxylation produce the substituted acetone.
+ CO2 + EtOH
∆2) EtBr
1) NaOEt(a) 1) NaOEt
2)
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