UNIVERSIDAD DE LA AMAZONIA

FACULTAD DE CIENCIAS BÁSIC

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?
La formula C5H12 pertenece a un alcano saturado. Por tanto, los isó meros de la formula no
pueden tener dobles enlaces ni ciclos.
Los alcoholes que no presentan quiralidad (sin carbonos asimétricos son)

Los alcoholes que presentan quiralidad (con carbonos asimétricos) son

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.

Quiral Aquiral

Aquiral
Quiral
Quiral Aquiral

Aquiral Quiral

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?

Quiral
Quiral

Quiral
Quiral
 Aquiral
Aquiral

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.)

Enantiomero Estereoisomero

Diasteroisomero Enantiomero

Enantiomero Diasteroisomero

La misma moleculas dibujada de diferente forma Isomero constitucionales

 Diasteroisomero Moleuclas iguales

Diasteroisomero Diasteroisomero

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.

5. Which of the following are chiral?

Quiral Quiral Quiral Quiral

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

S
S R

R S
 S
R

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.

Br Br
Br Br CH3
CH3

H3CH2C H3CH2C

H 3C CH2CH3 H3C CH2CH3

S R S R

CH3
H3CH2C

H3C H H CH2CH3

R R

Br Br
R R

CH2CH3

Br Br
R R

H H
S R

CH2CH3

H H
S R
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?

Todos los compuestos con un plano de simetría tienen una imagen especular superponible y por
tanto son comuestos meso-aquirales.
a. 2,3-dichlorobutane
Cl
Cl Cl

Cl 1,3-dichlorocyclopentane
Aquiral
2,3-dichlorobutane
e. 1,3-dibromocyclobutane
Aquiral Br
b. 2,3-dichloropentane
Cl

Br
1,3-dibromocyclobutane
Cl
f. 2,4-dibromopentane
2,3-dichloropentane
Br Br
c. 2,3-dichloro-2,3-dimethylbutane

Cl Cl
2,4-dibromopentane
Aquiral
2,3-dichloro-2,3-dimethylbutane g. 2,3-dibromopentane
Aquiral
d. 1,3-dichlorocyclopentane
 Br

Br 1,2-dimethylcyclopentane
2,3-dibromopentane Aquiral
h. 1,4-dimethylcyclohexane
j. 1,2-dimethylcyclobutane

1,4-dimethylcyclohexane
Aquiral 1,2-dimethylcyclobutane
i.1,2-dimethylcyclopentane Aquiral
11. Indicate whether each of the following structures is (R)-2-chlorobutane or (S)-2-chlorobutane.
S R
Cl CH3
Cl
(R)
H CH3 H Cl

CH2CH3 CH2CH3

R
CH3

H Cl

CH2CH3

R R

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

a. trans-3-methyl-3-hexene

b. 2-chloro-cis-2,trans-heptadiene
Cl
c. (ctfis-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?
Β-caroteno

Vitamina A

Para ambas moléculas todos los doble enlaces unidos al anillos tienen configuració n trans y los
carbonos son aquirales.

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

a. 2,3-dimethylbutane (sawhorse)

b. 1,2-dibromo-1,1,2,2-tetrafluoroethane (Newman)
 Br

F F

F Br F
c. the d,l isomers of 1-chloro-1-fluoroethane (Newman)

Br H

H F H

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

H OH

H C6 H5 H
a)
H

Br Cl

H H
b) H

CN

H H

H2N H H
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

configuration meso
 H H

(S) (R)
Cl Cl
b. 1,4-dichlorocyclohexane

configuration meso

(s) Cl

(s)
H

Cl
c. 1,3-dichlorocyclohexane

configuration meso

Cl Cl

(R) (S) H
H

d. 2,3-dichloropentane

configuration meso

Cl

(R) (R)

Cl
e. 2,3,4-trichloropentane

configuration meso

Cl Cl

(R) (s) (S)

Cl
f. 2,3,4,5-tetrachlorohexane

configuration meso
 Cl Cl

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

Cl Cl

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

Cl
Cl
H
(R)
(R)
H

3-chloro-1-butyne

Enantiomero
b. 4-chloro-1-butyne

Cl

Ninguno
c. 1-chloro-1,3-butadiene

Cl

Cl

Isó mero cis-trans

d. 2-chloro-1,3-butadiene

Cl

Ninguno
e. 4-chloro-2-pentene
 Cl Cl Cl

Isómero cis-trans y enantiomero

f. 5-chloro-2-pentene

Cl Cl

Isómero cis-trans

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

Cl

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)

Enantiomero
b)

Diasteroisomero
c)
Enantiomero
d)

Isomeros identicos
e)

Isomero cis, trans

f)

Enantiomeros