Problem Set #2

1. Provide systematic (IUPAC) names for each of the following structures:

Cl

F
Cl Br
1 propyl, 2 t-butyl cyclobutane

2 bromo, 4 chloro, 3,4 dimethyl hexane

3 chloro, 4 ethyl, 1 fluoro, 6 methyl heptane

Cl

1 butyl, 3 isobutyl cycloheptane 2,3,3 trimethyl pentane

1 chloro, 3 sec butyl cyclooctane

CH3
Cl

Cl Cl
CH3

cis-1,3 dimethyl cyclohexane 2,2 dichloro hexane

OH

trans-1 chloro, 4 hydroxy cyclohexane

Br

Br 2 bromo, 5 ethyl, 4 methyl heptane

4 ethyl, 5 methyl octane

1 bromo, 3 methyl, 5 propyl cyclohexane
 2. Provide the correct structures for the following IUPAC names:

Cl
Cl
Br Cl

1-bromo-2,2-dimethylpropane 1,1,1-trichloro-3-ethyl-5-methyloctane

Cl Cl
F
Cl Br

4-(1-methylethyl)nonane 3-bromo-2,2,3-trichloro-1-fluorobutane

1-sec-butyl-4-isopropylcycloheptane 1-butyl-3-isobutyl-5-pentyl-2-propylcyclohexane

cis-1,3-dimethylcyclobutane trans-1,2-diiodocyclohexane
 3. Draw the most stable Newman projection of 1,2-dibromoethane.

Br H
H most stable conformer of the compound is staggered
H with the two largest atoms, bromine, as far apart as
H Br possible.

Remeber for Newman projections:

Br
H H

H H
first carbon Br
second carbon you see when
you see when looking down
looking down C-C bond
C-C bond

4. Draw the most stable Newman projection of pentane looking down the C2-C3
bond.

H2
H3C C CH3
1 C C 5
H2 3 H2
2 4
Most stable conformer is staggered, with the two alkyl
substitutents (methyl on C1 and Ethyl on C2) as far apart
as possible

CH3
H H
H 3C 2 H H
3 CH CH
2 3
H H
H H
CH2CH3
5. Draw the two chair conformers of 1-bromocyclohexane and indicate which one is
more stable:

Br

Br

H
Br

More stable; substituent is equatorial

6. Convert the following stick structure to the appropriate chair conformer(s).

CH3

CH3

CH3
Methyls are trans!

CH3

CH3
H
H
OR H CH3

H3C CH3 H
7. Draw the bond rotation energy diagram for 2-methylbutane (looking down the C2-C3
bond) with the Newman projections for each point

H3C CH3 H CH3

H CH3
H CH3 H CH3
H CH3 H H
H
H CH3
H3C

E
N
R CH3
G CH3 H CH3
H3C H
Y CH3
(!E) H H CH3 CH3
H H CH3 H H H
H
H CH3
CH3 H CH3
CH3

Dihedral Angle