UNIVERSIDAD DE LA AMAZONIA

FACULTAD DE CIENCIAS BÁSICAS

PROGRAMA DE QUÍMICA
ASIGNATURA: QUÍMICA ORGÁNICA I
TALLER: ESTEREOQUÍMICA

1. Which of the isomeric alcohols having the molecular formula C 5H12O are chiral? Which are
achiral?

2. In each of the following pairs of compounds one is chiral and the other is achiral. Identify each
compound as chiral or achiral, as appropriate.

3. Compare 2,3-pentanediol and 2,4-pentanediol with respect to the number of stereoisomers

possible for each constitution. Which stereoisomers are chiral? Which are achiral?

4. Identify the relationship in each of the following pairs. Do the drawings represent constitutional
isomers or stereoisomers, or are they just different ways of drawing the same compound? If they
are stereoisomers, are they enantiomers or diastereomers? (Molecular models may prove useful in
this problem.)
5. Chemical degradation of chlorophyll gives a number of substances including phytol. The
constitution of phytol is given by the name 3,7,11,15-tetramethyl-2-hexadecen-1-ol. How many
stereoisomers have this constitution?
Specify the configuration at R or S in each of the following.

6. Which of the following are chiral?

7. Specify the configuration at R or S in each of the following.

8. What stereoisomers would you expect to obtain from each of the following reactions? Specify
the configuration at R or S in each of the following.

9. Mevacor® is used clinically to lower serum cholesterol levels. How many asymmetric carbons
does Mevacor® have?

10. Which of the following compounds have an achiral stereoisomer?

a. 2,3-dichlorobutane f. 2,4-dibromopentane
b. 2,3-dichloropentane g. 2,3-dibromopentane
c. 2,3-dichloro-2,3-dimethylbutane h. 1,4-dimethylcyclohexane
d. 1,3-dichlorocyclopentane i. 1,2-dimethylcyclopentane
e. 1,3-dibromocyclobutane j. 1,2-dimethylcyclobutane

11. Indicate whether each of the following structures is (R)-2-chlorobutane or (S)-2-chlorobutane.

12. Draw structures showing the configuration of the following compounds.

a. trans-3-methyl-3-hexene
b. 2-chloro-cis-2,trans-heptadiene
c. (cis-1-propenyl)cyclobutane
d. trans-1,2-di-(cis-1-propenyl)cyclobutene

13. Examine the structures of β-carotene and vitamin A and determine the configuration at each of
the double bonds in the chain attached to the ring(s). Are these substances chiral or achiral?

14. Draw the staggered conformations of each of the following compounds using the indicated
convention:

a. 2,3-dimethylbutane (sawhorse)
b. 1,2-dibromo-1,1,2,2-tetrafluoroethane (Newman)
c. the d,l isomers of 1-chloro-1-fluoroethane (Newman)

15. Draw a staggered conformation in both the sawhorse and Newman representations that
corresponds to the configurations shown in the projection formulas a-c.

a)

b)

c)

16. From the compounds listed select all those that may have achiral meso configurations and
draw the configurations for each of them.

a. 1,2-dichlorocyclopropane
b. 1,4-dichlorocyclohexane
c. 1,3-dichlorocyclohexane
d. 2,3-dichloropentane
e. 2,3,4-trichloropentane
f. 2,3,4,5-tetrachlorohexane

17. Which of the following compounds can exist as (1) a pair of enantiomers, (2) a pair of cis-trans
isomers, and (3) as a cis pair of enantiomers and a trans pair of enantiomers?

a. 3-chloro-1-butyne
b. 4-chloro-1-butyne
 c. 1-chloro-1,3-butadiene
d. 2-chloro-1,3-butadiene
e. 4-chloro-2-pentene
f. 5-chloro-2-pentene

18. Write structures showing the specified configurations for each of the following compounds.
Make your drawings as clear as possible so there is no ambiguity as to structure or configuration:

a. cis-1,2-diphenylethene
b. trans-2-chloro-2-butene
c. trans-1-propenylbenzene
d. trans-trans-2,4-heptadiene
e. cis-cis-2,4-heptadiene
f. trans-cis-2,4-heptadiene
g. cis-trans-2,4-heptadiene
h. cis-1-tert-butyl-4-methylcyclohexane

19. Determine the relationship between the pairs of compounds written as perspective formulas
as being enantiomers, diastereomers, conformational isomers, cis-trans isomers, or some
combination of these. Models will be very helpful

a)

b)

c)

d)

e)
f)