STRUCTURAL ISOMERISM
Isomers are different compounds that have the same chemical formula. In other
words, these are group of atoms with the same molecular formula but different
arrangement of atoms. For example,
and
both have a C4H8 molecular formula, but have different structures. A molecular formula
can provide the actual number of atoms in a compound, but never the arrangement of
atoms. This mean that two or more compounds may have exactly the same molecular
formula, but may not have the same structure. There are several types of isomers and
these are shown below.
isomer
constitutional
isomers stereoisomers
skeletal positional functional enantiomers diastereomers
configurational cis-trans
diastereomers diastereomers
Constitutional isomers (also known as structural isomers) are those whose
atoms are connected differently; thus having different structures. For this discussion, we
will focus only on this type of isomer. There are three types of structural isomers, namely
skeletal, functional, and positional isomers.
Skeletal isomers differ in carbon linkages found in the “skeleton” chains. The
skeleton chain or the parent chain is the longest carbon chain.
Positional isomers only differ in the attachment of the functional group to the parent
chain.
Functional isomers are two or more compounds having the same molecular
formula but different functional groups.
Skeletal Isomers
Also known as chains isomers, these isomers arise because of the possibility of
branching in carbon chains. An example is butane, C4H10, which has two chain isomers.
In one of them, the carbon atoms lie in a "straight chain" (1) whereas in the other the
chain is branched (2).
(1) CH3—CH2—CH2—CH3
CH3
(2) |
CH3—CH—CH3
In naming branched compounds, take note of the following.
Guide Questions during Practice
Step 1 How many carbon atoms are present in the longest chain? How
many carbon atoms are present in the branch? (The number of
carbon atoms will determine the prefix necessary for both the
longest chain and the branch. Branch name will use the suffix ‘–yl’)
Step 2 Are there multiple bonds between two carbon atoms or functional
group? What family does the compound belong to? (Each family of
organic compounds has a unique method of naming. Alkenes,
alkynes, and alcohols considers the location of the functional
group.)
Step 3 What is the name of the compound? (The branch is usually written
first.)
Problems
Name the following branched compounds.
a. CH3 b. CH3
| |
CH3—CH—CH3 CH3—CH—CH2—CH3
Solutions
a. CH3
|
CH3—CH—CH3
Step 1 How many carbon atoms are present in the longest chain? How
many carbon atoms are present in the branch? 3, 1
Step 2 Are there multiple bonds between two carbon atoms or functional
group? What family does the compound belong to? No
Step 3 What is the name of the compound? 2-methylpropane
b. CH3
|
CH3—CH—CH2—CH3
Step 1 How many carbon atoms are present in the longest chain? How
many carbon atoms are present in the branch? 4, 1
Step 2 Are there multiple bonds between two carbon atoms or functional
group? What family does the compound belong to? No
Step 3 What is the name of the compound? 2-methylbutane (This is a chain
isomer of pentane.)
Positional Isomers
In positional isomerism, the basic carbon skeleton (longest carbon chain)
remains unchanged, but important groups are moved around on that skeleton. For
example, there are two structural isomers with the molecular formula C3H7Br. In one of
them the bromine atom is on the end of the chain (1), whereas in the other it's attached
in the middle (2).
(1) CH3—CH2—CH2—Br (2) CH3—CH—CH3
|
Br
1-bromopropane 2-bromopropane
Functional Isomers
In this variety of structural isomerism, the isomers contain different functional
groups - that is, they belong to different families of compounds (different homologous
series). In the previous lesson, the families of compounds were discussed by two. Except
for amine and amide, these families are actually functional isomer of one another: alcohol
and ether, aldehyde and ketone, and carboxylic acid and ester. For instance, if you
happen to see a similar compound formula from alcohols and ether, these two are
functional isomers of one another. Take ethanol and dimethyl ether as an example. Both
compounds have exactly the same chemical formula but have different structures.
ethanol dimethyl ether
