A.

Romero 2007
Types of Isomers
CHEM 1B

Isomers are compounds that have the same chemical formula, but the atoms in the compound are
arranged differently. Two isomers will therefore have different properties.

Isomers

Structural Isomers Stereoisomers

Coordination Linkage Geometric Optical

Isomerism Isomerism Isomerism Isomerism

Structural Isomers have the same atoms, but they are bonded differently (atoms are connected
with different atoms)

Coordination Isomerism occurs when groups of Lewis bases are connected to the central
metal in different ways. A Lewis base that is also an anion can be connected either with a
coordinate covalent bond, or with an ionic bond.

pentaamminebromochromium(III) sulfate pentaamminesulfatochromium(III) bromide

Linkage Isomerism occurs when a group attached to a molecule has more than one atom that
can form bonds. If the group is attached to the molecule though different atoms, then these
molecules are linkage isomers of each other.

tetraamminechloronitrocobalt(III) chloride tetraamminechloronitritocobalt(III) chloride

Stereoisomers have the same atoms bonded in the same way, but the spatial arrangements of the
bonds are different.

Geometric Isomerism occurs due to cis- and trans- arrangements around a rigid ring or
bond.

Optical Isomerism occurs

around a chiral center. If an
atom is bonded to four different
groups, its mirror image can not
be rotated and superimposed onto
the original molecule. Therefore,
distinctly different molecules can
be formed from the same atoms
around a chiral center. Isomers
with nonsuperimposable mirror
images are called enantiomers.
The carbon in the figure to the
right is an example of a chiral
center. These isomers are called
optical isomers because they
rotate plane-polarized light in
opposite directions.
Optically Active Substances:

Figure 21.13 (Page 1006)

Zumdahl, S. and S. Zumdahl, Chemistry, 6th ed.,
Houghton Mifflin Company, Boston, 2003.

 A polarizing filter blocks all light except that which is oscillating in a specific plane.

 An optically active substance will rotate the plane in which the light is oscillating. This rotation
can be measured using another polarizing filter.

 Optical isomers will rotate plane polarized light in opposite directions.

 dextrorotary (d): a species that rotates plane polarized light to the right (looking
down the beam). The sample in figure 21.13 is dextrorotary.

 levorotary (l): a species that rotates plane polarized light to the left (looking
down the beam).

 A racemic mixture (containing equal amounts of both optical isomers) will not
rotate plane polarized light since the optical effects of the two isomers cancel each
other out.

Note: lower case d- and l- prefixes refer to the optical rotation properties of the substance (for
example d-glucose is dextrorotary). The commonly used capital D- and L- prefixes are a
designation of the configuration of atoms around a specific carbon, and not necessarily related to
the optical properties (for example d-glucose is D-glucose, but l-fructose is also D-fructose since
they both have the same configuration around the fifth carbon atom, C5).
Test Your Knowledge:

1) What type of isomerism is shown below?

a) coordination isomerism
b) linkage isomerism
c) geometric isomerism
d) optical isomerism
e) these two compounds are not isomers

2) How many chiral carbons are in D-glucose molecule shown to the right? Mark each chiral
carbon (if any) with an asterisk.

a) 0
b) 2
c) 4
d) 5
e) 6
Answers:

1) C
The compounds are isomers, because they have the same formula, but the atoms are
arranged differently. The isomers must be stereoisomers rather than structural isomers,
because both compounds contain the same bonds between atoms (in structural isomers
different atoms are bonded to each other, or the atoms are bonded in a different way). The
isomers are not optical isomers, because a mirror image of each isomer could be rotated
and superimposed on the original compound. Therefore, theses are geometric (cis- and
trans-) isomers. The figure on the left is the trans- isomer, and the figure on the right is
the cis- isomer.

2) C
The carbon atoms must be bonded to four different
groups to be chiral. The top carbon (C1) is only bonded
to three groups and can not be chiral (a mirror image
could be rotated along the vertical axis and super
imposed). C2 through C5 are chiral because the four
bonded groups around each carbon are different. The
bottom carbon (C6) is not chiral because even though it is
bonded to four groups, two of them are the same (the
hydrogen atoms).