1. What are isomers?

Isomers are molecules that have the same molecular formula, but have a different
arrangement of the atoms in space. That excludes any different arrangements which are
simply due to the molecule rotating as a whole, or rotating about particular bonds.

2. Give five different types of isomers and give one example each.
Constitutional isomers are compounds that have the same molecular formula and different
connectivity. To determine whether two molecules are constitutional isomers, just count the
number of each atom in both molecules and see how the atoms are arranged.

example: 1-propanol, 2-propanol and ethyl methyl ether (C3H8O)

Stereoisomers are isomeric molecules that have the same molecular formula and sequence of
bonded atoms (constitution), but differ in the three-dimensional orientations of their atoms in
space. In chemistry, conformational isomerism is a form of stereoisomerism in which
the isomerscan be interconverted exclusively by rotations about formally single bonds (refer to
figure on single bond rotation).

example : butane : staggered (left) and eclipsed (center).The C2-C3 sigma bond rotation
is animated (right). Try rotating the model to look along the C-C to see the two forms.

Configurational isomers are stereoisomers that can cannot be converted into one another by
rotation around a single bond. The two main types of configurational isomers are
geometric isomers and optical isomers. Geometric isomers are molecules that are locked
into their spatial positions with respect to one another due to a double bond or a ring structure.

(E)-2-butene and (Z)-2-butene

Optical isomers are molecules that differ three-dimensionally by the placement of substituents
around one or more atoms in a molecule. Optical isomers were given their name because they
were first able to be distinguished by how they rotated plane-polarized light. Either of two
stereoisomers that are mirror images of one another but cannot be superimposed on one
another and that rotate the plane of polarized light in opposite directions.
Enantiomers usually behave the same chemically but differ in optical behavior and sometimes
in how quickly they react with other enantiomers.

(R)- or (S)-2-chlorobutane. Try moving the images to show that they are mirror images.

Diastereomers (sometimes calleddiastereoisomers) are a type of a stereoisomer.

Diastereomerism occurs when two or more stereoisomers of a compound have different
configurations at one or more (but not all) of the equivalent (related) stereocenters and are not
mirror images of each other.

(S,R)- or (R,R)-2-bromo-3-chlorobutane.

3. Do isomers have the same physical properties? Chemical properties? Why?

The overall shape of a molecule, which generally differs between isomers, affects its physical
properties. In the case of alkanes, this can be seen when the amount of branching is increased or
decreased. A long, single chain of carbon atoms has a large surface area, resulting in a lot of
interactions with neighboring molecules, which increases the melting and boiling points. A highly
branched alkane has much less room for interaction, giving it lower melting and boiling points.
The chemical properties of a molecule also depend on the arrangement of the atoms, especially
when the functional groups differ. As an example, consider propanol, with the formula
CH3CH2CH2OH. An isomer of this is methoxyethane, CH3CH2OCH3. Propanol is an alcohol and
undergoes very different reactions than an ether like methoxyethane.