Download packet 3, 2323

Organic Chemistry I
CHEM 2323
Packet #3
1.
Consider the following molecule.
Br
Cl
Label all chiral atoms as either R or S.
Draw the compound in Newman projection (looking down the C2-C3 bond) and Fischer
projection.
Draw a diastereomer in Newman projection.
Draw an enantiomer in Fischer projection.
2.
Label all chiral atoms in the following drug compounds as R or S.
HS
HO
O
N
O
H
HO
OH
HO
captopril
(used for high blood pressure)
O
O
OH
ascorbic acid
(vitamin C)
Cl
Cl
Br
Cl
Br
halomon
(antitumor agent)
3.
In a later chapter we will learn a bromination reaction (br2, hν), which replaces a
hydrogen atom with a bromine atom. Consider the following compounds and perform one
bromination that replaces the indicated hydrogen atom with a bromine atom. The bromine can
attach on either face (coming out of the page or into the page).
H
H
H
Draw all stereoisomer obtained.
Label all chiral atoms as R or S.
Which compounds will yield exactly a 50/50 ratio of stereoisomers? Which will yield a different
ratio? Why?