Me Me O Me OBn LiAlH4 Me Me O Me OTBDPS LiAlH4 O OBz O Me

Lecture 11/12
Practice Problems
Please predict the products of each of the following transformations and rationalize your predicted stereochemistry.
H
MeMgBr
Ph
O
Me
OSiMe2(t-Bu)
H
Ph
t-Bu
O
Me
O
Me
Me
Me
OBn
O
Me
Me
Me
LiAlH4
LiAlH4
OTBDPS
Please explain the observed stereochemistry of the following reaction.
OBz
Me
O
H
O
Et Me
EtMgBr
Et2O
OBz
H
Et
Me OH
O
Et Me
1