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 (*)

NH2

∗∗∗∗H3C

O

OH∗∗∗∗H3C

O

OH

C∗∗∗∗

CF3

ClHBr

C∗∗∗∗

CF3

Cl HBr

∗∗∗∗ ∗∗∗∗HO

CH3

∗∗∗∗∗∗∗∗ OH

CH3

∗∗∗∗∗∗∗∗ ∗∗∗∗ ∗∗∗∗

C

CF3

ClHH

C

CF3

Cl HH

NH2

Enantiomers Diastereomers Neither

Enantiomers Diastereomers Neither

Enantiomers Diastereomers Neither

Enantiomers Diastereomers Neither

Enantiomers Diastereomers Neither

2. Draw (R)-2-aminobutane, clearly indicating stereochemistry with wedge and dashbonds. Use the back if necessary.

NH2

Chem 331 Quiz 4 Name:______________________________

1. The antibiotic amoxicillin contains a number of stereocenters. Circle eachstereocenter, and write the number of possible stereoisomers of amoxicillin. (3 points)

24 = 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 Ror S isomer. (3 points)

O

Cl

NH

Ketamine

O

Cl

NH1

2

34

O

Cl

NH1

2

34redraw

Assign priority clockwise = R3. Circle all of the chiral molecules. (4 points)

O

(R)

O

HO

NH

Cl Br

OH

H2N

O

NH

ON

S

OHO

Amoxicillin

Chem 331 Quiz 2 Name:______________________________

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-dimethylcyclohexene 1,4 butanediol

Cl

12

3

4

56

1

2

3

4HO

OH

3. Fill in and label (gauche, anti, eclipsed) the newman projections for the MOST andLEAST 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 – CH3 groups have to remain cis to each other.

OH

H

H

H

CH3

H

H3CH

CH3 H

CH3

CH3

CH H

CH3

HHC

CH3

CH H

CH3

CH H

Chem 331 Quiz 1 Name:______________________________

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

CC F

F

F

F

Always draw lone pairs!

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

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 atomsshown in the boxes. (3 pts)

Aldehyde

N N N HN

O

O O

CC

H

O

H

HH

sp2

sp3