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Chem 331 Quiz 5Name:______________________________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 (*)
NH
2
∗∗∗∗
H
3
COOH
∗∗∗∗
H
3
COOHC
∗∗∗∗
CF
3
ClHBrC
∗∗∗∗
CF
3
Cl HBr
∗∗∗∗∗∗∗∗
HOCH
3
∗∗∗∗∗∗∗∗
OHCH
3
∗∗∗∗∗∗∗∗ ∗∗∗∗ ∗∗∗∗
CCF
3
ClHHCCF
3
Cl HHNH
2
Enantiomers
Diastereomers NeitherEnantiomers
Diastereomers
Neither
Enantiomers
Diastereomers NeitherEnantiomers Diastereomers
Neither
Enantiomers Diastereomers
Neither
2. Draw (
 R
)-2-aminobutane, clearly indicating stereochemistry with wedge and dashbonds. Use the back if necessary.
NH
2
 
Chem 331 Quiz 4Name:______________________________1. The antibiotic amoxicillin contains a number of stereocenters.
Circle
eachstereocenter, and write the number of possible stereoisomers of amoxicillin. (3 points) 
2
4
= 32 steroisomers
2. The two stereoisomers of the club drug/anaesthetic ketamine behave differently in thebody.
S
-ketamine is an anaesthetic and hypnotic, while
 R
-ketamine causes hallucinationsand can lead to seizures. Indicate whether the structure of ketamine drawn below is the
 R
or
S
isomer. (3 points)
OClNHKetamineOClNH
1
234OClNH1234redrawAssign priorityclockwise = R
3. Circle all of the chiral molecules. (4 points)
O
(R)
OHONHCl Br
OHH
2
NONHONSOHOAmoxicillin
 
Chem 331 Quiz 2Name:______________________________1. The compound shown below is one of the major components of the odor of freshly cutgrass. Provide an IUPAC name for this compound, and indicate the configuration aroundthe double bond (cis/trans). (2 pts)
 cis
-3-hexenol
2. Draw the structures indicated by the IUPAC names below. (2 pts)
4-chloro, 1,3-dimethylcyclohexene1,4 butanediol
Cl123456
1234HOOH
3. Fill in and label (gauche, anti, eclipsed) the newman projections for the
MOST
and
LEAST
stable conformers of butane. (4 pts) 
Eclipsed Anti
4. Below is the chair conformation for
cis
-1,3-dimethylcyclohexane. Draw the structurethat would result from a chair flip, and predict the energy difference between the twostructures. (2 pts)
No energy difference (same molecule)Axial becomes equatorial, and vice versa – CH
3
groups have to
 remain cis
to each other.
OHHH
HCH
3
HH
3
CHCH
3
HCH
3
CH
3
CH HCH
3
HHC
CH
3
CH HCH
3
CH H
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msibby

Jacob, tried finding your e-mail...just wanted someone else to know that I attempted to e-mail Dr. Bryson to let him know I would like to take the final at 5pm as opposed to the 3:30pm time slot...Thanks...Mike

reply12 / 10 / 2009
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