Chem 331 Quiz Keys

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 ∗ C H Cl Br

CH3 HO

∗∗

CF3 C Cl H Br ∗

Diastereomers

Neither

Enantiomers

Diastereomers

Neither

Enantiomers

Diastereomers

Neither

CH3 ∗∗

O H3C ∗

Enantiomers

OH

O OH

H3C ∗

OH

NH2

NH2

∗

∗

∗

CF3 C H Cl H

∗

CF3 C Cl H H

Enantiomers

Diastereomers

Neither

Enantiomers

Diastereomers

Neither

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)

HO

O O N

O

S

OH

N H

24 = 32 steroisomers

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 4

3

NH

NH

Cl redraw 4

3 NH 1 2 O

1 O

2 O Assign priority

Ketamine

clockwise = R

3. Circle all of the chiral molecules. (4 points) Cl

HO

Br

(R)

O

O

N 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 5

Cl

6 1

1,4 butanediol

4 2

1

3

3

HO

2

OH 4

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

CH3 C H H H

H CH3 C

H

C

H

CH3 CH3 C 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

C

F

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

O

N O

3. For

O

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

C C

C H

C O

O H

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

O

Aldehyde

H

sp2

C C

H H

sp3

H