Problem Set 3

1) Indicate the chiral centers in the following molecules

*
Cl
* Br
*
OH

* *
O O *
* Br
* *
* * * *
* Cl
O
*
O
*
O

2) Determine R & S for all the stereocenters of the following molecules

Cl
(R) (S) (R)
HO (S) (S)
(R)

(R)
(R) Cl
HO (R)
(S)
Cl

(S)
Cl
OH
(R) OH
(S) (S)
F (S) (R)
Br
Br
3) Give the proper IUPAC names of the following molecules:

Cl
OH
Cl
(2S,3S)-4-ethyl, 2-hydroxy-hexane
(4R,5R)-4,5-dichloro octane

OH

HO

(1R,2R,4S)-2-ethyl-4-methylcyclohexanol
(2S,5S)-5-ethyl-2-nonanol

4) Provide the correct structure for the following IUPAC names:

(3R,6R)-6-ethyl-3-hydroxy nonane (1R,3R)-1-ethyl-3-methylcyclohexane

HO

(1R,3R)-3-chlorocyclopentanamine (2S,4R)-2-bromo-4-methylhexane
Br
Cl
NH2

(2S, 4S)-2-chloro-4-methyl-hexane (3S,4S)-3-methyl-4-chloro heptane

Cl Cl
5) Indicate if the following pairs are constitutional isomers, diastereomers, enantiomers,
or identical

a. Br Cl Br
(R)
(R)
(S) (S) c. (R) (S) (R) Cl
(R)

diastereomers
enantiomers

OH (R) (R)
b. Cl OH (S)
d. Cl
(S) (S) (S) Cl
Cl (S) (R) OH
HO
identical
diastereomers

6) Draw all of the stereoisomers for 1,3-dimethylcyclopentane. Label each stereocenter

as R and S. If a meso compound exists, circle it.

* *
22 = 4 possible stereoisomers

(R) (R) (S) (S) (R) (S)

Only get three stereoisomers since one is a meso compound