Additional Problems for Practice: 1.How would you prepare ...
Additional Problems for Practice:
1.How would you prepare these compounds using either an acetoacetic ester synthesis or
a malonic ester synthesis?
O
O
O
O
a.
EtO
1. NaOEt
2. Br
Br
EtO Br H
O
CH3
H3O+, heat -CO2
NaOEt
O
O
EtO
O
O
1. NaOEt
b.
EtO
2.
OEt
O
EtO H
O OEt
Br
NaOEt
COOH
H3O+, heat -CO2
O EtO
O OEt
O
O
1. NaOEt
O
O
C
c.
EtO
OEt
2.
Br
EtO
OEt
C N
POCl3
O H2N
1. SOCl2 2. NH3
H3O+ heat
O HO
d.
O EtO
O OEt
1. NaOEt
2.
Br
O
EtO H
O OEt
1. NaOEt 2. CH3I
O
EtO H3C
O OEt
O N(CH3)2
H3O+ heat
1. SOCl2
H
2. (CH3)2NH H3C
O OH
2.How would you prepare the following compounds from cyclohexanone?
a.
O
O
NaOH
2 xs. H
O
double aldol; dehydration
O
b.
NaOH
O
O
O
OCH2CH3
H3CH2CO
OCH2CH3
O
N
N
c.
H
pH 4.5
N
CN
CN
H3O+
O CN
O
d.
O OEt
1. NaOEt
O
O
O
OEt
H3O+
2.
Br
heat
-CO2
3.Propose a mechanism to account for the following reactions:
a.
O
O
NaOH
O
CH3CH2OH
HO
NaOH
O-
O
Michael addition
O -O
O-
O
CH3CH2OH
O
aldol
O
NaOH
O
CH3CH2OH
HO
b.
O OCH3
(CH3)2CuLi
CH3 Li+ Cu
CH3
O OCH3
1,4-addition
O
O
OCH3 CH3
nucleophilic acyl substitution
O OCH3 O-
-O
OCH3O
OCH3
OCH3
CH3
4. How could you prepare the following cyclohexenones by combining a Stork reaction
with an intamolecular aldol condensation?
a.
O
N H
H+, -H2O
O HO CH3
NaOH
N
O
N
NaOH
O
O-
O-
H3O+ -
N H
O
O
O HO CH3
O CH3
similarly: b.
N
O
O+
O
CH3
5.Show a mechanism for the following reactions:
O
a.
EtO
O
+ CH2O
CH3
NaOEt,
EtOH, heat
O
+ CO2 + EtOH
CH3
NaOEt
O
O
EtO
CH3
HH
O
H
O
O
NaOEt
O
EtO
CH3 H
OH
EtO
EtOH
OCH3
-CO2
H O
O
O
-EtO-
CH3
O
EtO
HO-
O
CH3 OH
-HO-
O
CH3
O
CH3
O
b.
O
+
CH3
O
O
EtO
CH3
H
O
O
NaOEt,
EtOH,
EtO
CH3
heat
CH3
EtO2C
-O O
EtOH
O O
EtO-
EtO2C
CH3
EtO2C
CH3
-O
O
EtO2C
CH3
EtOH
O EtO2C
OH CH3
EtO-
O EtO2C
H OH CH3
O
EtO2C
CH3
c.
O
O
+ ClCH2CO2CH2CH3
NaOEt,
OCH2CH3
EtOH,
O
NaOEt
O
Cl EtO
addition
H
-O Cl
SN2
OCH2CH3
O
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