S.

Lievens,
University of California, Davis

March 2012
For use in UCDavis Chemistry 8/118 Series

Assigning Stereochemistry VI

E and Z in Alkenes
Alkenes can have multiple geometric isomers (non-superimposable, nonmirror images)
If there are exactly two substituents and two hydrogens attached an
alkene the isomer may be labeled as cis- or trans-.
H

H
a trans alkene
H opposite

R'

vs.

R
R'

a cis alkene
H on same side

If there are two or more substituents attached to an alkene the isomer may
be labeled as E or Z
o All cis- molecules are Z, but not all Z molecules are cis-; all transmolecules are E, but not all E molecules are trans-. Cis- and transare accepted when appropriate, but E and Z work for all
asymmetrical alkenes.

Assigning Relative Configuration: E vs. Z

o For each sp2 carbon in the alkene identify the two substituents and
prioritize them 1 and 2 using the Cahn-Ingold-Prelog Rules.
See Assigning Stereochemistry II
o If both high priority groups are on the same side of the alkene the
molecule is Z. (similar to a cis)
This can be remembered by Z is on the Zame Zide.
o If the high priority groups are on opposite sides of the alkene the
molecule is E. (similar to trans)
o If the there is no difference between the groups then the molecule
is symmetrical and thus E/Z is unnecessary. (e.g. monosubstituted
alkenes)

an E alkene
1st priority opposite 2 Y

W
Z 2

vs.

X1

X
Z 2

21

a Z alkene
1st priority on the same side

 S. Lievens,
University of California, Davis

March 2012
For use in UCDavis Chemistry 8/118 Series

Examples:

Compound A:
Br

assign priority

Br
H

2
2

1
1

High priority

(3Z)-4-bromo-3-pentenal

on the same side

Compound B:

assign priority

High priority

1
2

(3E)-3-methyl-3-hexene

on opposite sides

Compound C:
2

assign priority
Cl

High priority
(3E)-1-chloro-4-ethyl-5-methyl-3-hexene
Cl
on opposite sides

1
2

Compound D:
O

2H

assign priority

OH

High priority

OH

Br

Br 1

(2Z)-2-bromo-3-butenoic acid

on the same side

Compound E:
H B

assign priority

1
2

(2Z,4E)-2,4-heptadiene
or
cis,trans-2,4-heptadiene

A
2

H B

22

 S. Lievens,
University of California, Davis

March 2012
For use in UCDavis Chemistry 8/118 Series

Practice Examples:
Assign E or Z to each molecule.
Br

OCH3

OH

Cl
Br

Cl
A

CHO

COOH
Br

D
Br

SCH3CH2NH2
CN

Br

CN
Cl

HOOC
I

OH

OCH3

CN
CHO
N

M
O

OH

Br

OHC
Br

Cl

Cl

Cl
R

CBr3

Cl

Cl
U

23

 S. Lievens,
University of California, Davis

March 2012
For use in UCDavis Chemistry 8/118 Series

Practice Examples Key:

Br

(Z)

OCH3

OH

(E)

(E)

Cl

(Z)

Br

Cl
A

CHO

COOH
(E)
Br

D
Br

SCH3CH2NH2
(E)

CN

Br

(Z)

(Z)

CN

(E)

(Z)

(Z)

Cl

HOOC

(E)

OH

OCH3

CN

(E)

CHO

(Z)

(Z)

(E)

(E)

M
O
OH

Br

(E)

OHC

Br

(Z)

Cl

Cl

Cl

(E)

(E)

CBr3

Cl
(E)

(E)

(E)

Cl
U

24

(Z)