Chem 331 Quiz 5 Name:______________________________

1. For each PAIR of molecules:

a. Circle any chiral centers that are in the molecule.
b. Indicate if the pair of molecules are enantiomers, diastereomers, or neither.

Chiral centers are indicated with red asterisks (*)

CF3 CF3
∗ ∗
C C Enantiomers Diastereomers Neither
H Cl Cl H
Br Br

CH3 CH3
HO OH
∗∗ ∗∗ Enantiomers Diastereomers Neither

O O
H3C ∗ H3C ∗ Enantiomers Diastereomers Neither
OH OH
NH2 NH2

∗ ∗ ∗ ∗
Enantiomers Diastereomers Neither

CF3 CF3
C C Enantiomers Diastereomers Neither
H Cl Cl H
H H

2. Draw (R)-2-aminobutane, clearly indicating stereochemistry with wedge and dash

bonds. Use the back if necessary.

NH2
Chem 331 Quiz 4 Name:______________________________

1. The antibiotic amoxicillin contains a number of stereocenters. Circle each

stereocenter, and write the number of possible stereoisomers of amoxicillin. (3 points)

O
HO
O
N
O
S OH
N 24 = 32 steroisomers
H
H2N

Amoxicillin
2. The two stereoisomers of the club drug/anaesthetic ketamine behave differently in the
body. S-ketamine is an anaesthetic and hypnotic, while R-ketamine causes hallucinations
and can lead to seizures. Indicate whether the structure of ketamine drawn below is the R
or S isomer. (3 points)

Cl Cl Cl
4 3 3
redraw 4
NH NH NH
1 1
O 2 O 2 O
Assign priority clockwise = R
Ketamine
3. Circle all of the chiral molecules. (4 points)

Cl Br
HO
(R)

O N
O H
Chem 331 Quiz 2 Name:______________________________

1. The compound shown below is one of the major components of the odor of freshly cut
grass. Provide an IUPAC name for this compound, and indicate the configuration around
the double bond (cis/trans). (2 pts)

OH
cis-3-hexenol
H
H

2. Draw the structures indicated by the IUPAC names below. (2 pts)

4-chloro, 1,3-dimethylcyclohexene 1,4 butanediol

5
6 Cl
4 1 3
OH
1 3 HO
2 2 4

3. Fill in and label (gauche, anti, eclipsed) the newman projections for the MOST and
LEAST stable conformers of butane. (4 pts)

CH3 H H
C C
H H
CH3 CH3 CH3
C C
H H H H
Eclipsed Anti
4. Below is the chair conformation for cis-1,3-dimethylcyclohexane. Draw the structure
that would result from a chair flip, and predict the energy difference between the two
structures. (2 pts)

H
CH 3
H CH3
H3C

H CH3 H

No energy difference (same molecule)

Axial becomes equatorial, and vice versa – CH3 groups have to remain cis to each other.
Chem 331 Quiz 1 Name:______________________________

1. Tetrafluoroethylene, the raw material used in the manufacture of Teflon, has the
molecular formula C2F4. Draw a lewis dot structure for tetrafluoroethylene. (2.5 pts)

Always draw lone pairs!

F
C F
F C
F

2. Fill in the missing formal charges for the lewis dot structures shown below. (2.5 pts)

O O
N
N N N H
O
3. For each pair, circle the most polar bond. (2 pts)

C C C O C H O H

4. Name the functional group shown below, and indicate the hybridization of the atoms
shown in the boxes. (3 pts)

O sp2

Aldehyde H C
C sp3 H
H
H