O
Br
Br
O
OEt
OO
MeO OMe
OO
Br
Br
EtO OEt
OO
O
Br
OEt
OO
MeO OMe
OO
Br
OEt
OO
Br
Br
O
MeO Br O
O
O
O
Br
OO
O
O
OTs
O
O
OBr
OtBu
O
Br
O
CO2Me
HO2C CHO
N
O
O
MeO
H
H
O
I
Br
O
NaH
Chem 212
Enolate Problem Set Provide the products for the following reactions. Provide the correct mechanism. Indicate
whether the product(s) is(are) achiral, racemic or optically active.
1) LDA
2)
1) LDA
2)
1) Me2CuLi
2) H3O+
1) NaOMe
2)
1) NaOEt
2)
1) Et MgBr
2) H3O+
1) NaOEt
2)
3) H3O+, heat
1) NaOMe
2)
3) H3O+, heat
1) NaOEt
2)
1) LDA
2)
1) NaOEt
2) Et Br
3) NaOEt
4)
5) H3O+, heat
1) LDA
2)
3) H3O+
1) NaOEt
2) MeI
5-membered rings form faster than 7-membered ones
1) NaOMe
2)
1) LDA
2)
1) 1,2-ethanediol, H+
2) NH3, H2O, heat
3) LiAlH4
4) excess H3O+ (2 steps in one)
5) (conjugate addition!)
1) NaBH4, MeOH
2) Ac2O, pyridine
1) KOtBu
2) MeI
3) KOtBu
4)
1) NaOEt
2)
3) H3O+, heat
racemic