Chem 212

Condensation Reactions 3 ANSWERS

Suggest a synthesis of the following products from the starting materials given, more than
one step might be needed. There are usually many possible correct answers.

O O O 1) NaOMe
a) 2) O
?
MeO
3) H3O
1) NaOMe
O O O 2)
b) ? Br
O 3) NaOH
4) H , heat
O

c) H OH
?

1)
1) CH3CHO, NaOMe, warm 1) NaBH4, MeOH MgBr
2) NH2NH2, -OH, heat 2) PBr3 2) H3O+
3) BH3 OR 3) Mg OR 3) PCC
4) H2O2, -OH, H2O 4) O 4) NH2NH2, NaOH, heat
5) BH3
6) H2O2, -OH, H2O
5) H3O+
d) O
O
?
+ O
OMe
Ph3P
O H
1) NaOH, EtOH, warm

e) O O
H 2) HCN, H2O CN
?
OH
O 3) H3O , heat
OH
OH

O O
O OH 1) NaOEt
?
f) 2) LiAlH4 OEt
OEt OH 3) H3O