THE NAMES OF ORGANIC COMPOUNDS

Cracking the code

A modern organic name is simply a code. Each part of the name gives you some useful information about
the compound.
For example, to understand the name 2-methylpropan-1-ol you need to take the name to pieces.
The prop in the middle tells you how many carbon atoms there are in the longest chain (in this
case, !.
The an which follows the "prop" tells you that there aren#t any carbon$carbon double bonds.
The other two parts of the name tell you about interesting things which are happening on the first
and second carbon atom in the chain. Any name you are likely to come across can be broken up in
this same way.
Counting the carbon ato!
%ou will need to remember the codes for the number of carbon atoms in a chain up to & carbons. There is
no easy way around this $ you have got to learn them. 'f you don#t do this properly, you won#t be able to
name anything(
code no o" carbon!
meth )
eth *
prop
but +
pent ,
hex &
T#$e! o" carbon%carbon bond!
-hether or not the compound contains a carbon$carbon double bond is shown by the two letters
immediately after the code for the chain length.
code ean!
an only carbon$carbon single bonds
en contains a carbon$carbon double bond
For example, butane means four carbons in a chain with no double bond.
Propene means three carbons in a chain with a double bond between two of the carbons.
A&k#& grou$!
.ompounds like methane, ./+, and ethane, ././, are members of a family of compounds called
alkanes. 'f you remove a hydrogen atom from one of these you get an alkyl group.
For example0
A methyl group is ./.
An ethyl group is ././*.
These groups must, of course, always be attached to something else.
T#$e! o" co$ound!
The a&kane!
Example 1: -rite the structural formula for '%eth#&$entane.
1tart decoding the name from the bit that counts the number of carbon atoms in the longest chain $ pent
counts , carbons.
Are there any carbon$carbon double bonds2 3o $ an tells you there aren#t any.
3ow draw this carbon skeleton0
4ut a methyl group on the number * carbon atom0
5oes it matter which end you start counting from2 3o $ if you counted from the other end, you would draw
the next structure. That#s exactly the same as the first one, except that it has been flipped over.
Finally, all you have to do is to put in the correct number of hydrogen atoms on each carbon so that each
carbon is forming four bonds.
If you had to name this yourself:
.ount the longest chain of carbons that you can find. 5on#t assume that you have necessarily
drawn that chain hori6ontally. , carbons means pent.
Are there any carbon$carbon double bonds2 3o $ therefore pentane.
There#s a methyl group on the number * carbon $ therefore 2-methylpentane. -hy the number *
as opposed to the number + carbon2 'n other words, why do we choose to number from this
particular end2 The convention is that you number from the end which produces the lowest
numbers in the name $ hence *$ rather than +$.
Example 2: -rite the structural formula for '()%dieth#&butane.
1tart with the carbon backbone. There are + carbons in the longest chain (but! with no carbon$carbon
double bonds (an!.
This time there are two methyl groups (di! on the number * and number carbon atoms.
.ompleting the formula by filling in the hydrogen atoms gives0
Note* 5oes it matter whether you draw the two methyl groups one up and one down, or both up, or both
down2 3ot in the least( 'f you aren#t sure about drawing organic molecules, follow this link before you go
on. 7se the 8A.9 button on your browser to return to this page.
Example 3: -rite the structural formula for '('%dieth#&butane.
This is exactly like the last example, except that both methyl groups are on the same carbon atom. 3otice
that the name shows this by using 2,2- as well as di. The structure is worked out as before0
Example 4: -rite the structural formula for )%eth#&%'%eth#&he+ane.
hexan shows a & carbon chain with no carbon$carbon double bonds.
This time there are two different alkyl groups attached $ an ethyl group on the number carbon atom and
a methyl group on number *.
Filling in the hydrogen atoms gives0
Note* :nce again it doesn#t matter whether the ethyl and methyl groups point up or down. %ou might also
have chosen to start numbering from the right$hand end of the chain. These would all be perfectly valid
structures. All you would have done is to rotate the whole molecule in space, or rotate it around particular
bonds.
'f you aren#t sure about this, then you must read about drawing organic molecules before you go on.
If you had to name this yourself:
/ow do you know what order to write the different alkyl groups at the beginning of the name2 The
convention is that you write them in alphabetical order $ hence ethyl comes before methyl which in turn
comes before propyl.
The c#c&oa&kane!
'n a cycloalkane the carbon atoms are ;oined up in a ring $ hence cyclo.
Example: -rite the structural formula for c#c&ohe+ane.
hexan shows & carbons with no carbon$carbon double bonds. cyclo shows that they are in a ring.
5rawing the ring and putting in the correct number of hydrogens to satisfy the bonding re<uirements of the
carbons gives0
The a&kene!
Example 1: -rite the structural formula for $ro$ene.
prop counts carbon atoms in the longest chain. en tells you that there is a carbon$carbon double bond.
That means that the carbon skeleton looks like this0
4utting in the hydrogens gives you0
Example 2: -rite the structural formula for but%,%ene.
but counts + carbon atoms in the longest chain and en tells you that there is a carbon$carbon double
bond. The number in the name tells you where the double bond starts.
3o number was necessary in the propene example above because the double bond has to start on one of
the end carbon atoms. 'n the case of butene, though, the double bond could either be at the end of the
chain or in the middle $ and so the name has to code for the its position.
The carbon skeleton is0
And the full structure is0
'ncidentally, you might e<ually well have decided that the right$hand carbon was the number ) carbon,
and drawn the structure as0
Example 3: -rite the structural formula for )%eth#&he+%'%ene.
The longest chain has got & carbon atoms (hex! with a double bond starting on the second one (-2-en!.
8ut this time there is a methyl group attached to the chain on the number carbon atom, giving you the
underlying structure0
Adding the hydrogens gives the final structure0
8e very careful to count the bonds around each carbon atom when you put the hydrogens in. 't would be
very easy this time to make the mistake of writing an / after the third carbon $ but that would give that
carbon a total of , bonds.
Co$ound! containing ha&ogen!
Example 1: -rite the structural formula for ,(,(,%trich&oroethane.
This is a two carbon chain (eth! with no double bonds (an!. There are three chlorine atoms all on the first
carbon atom.
Example 2: -rite the structural formula for '%broo%'%eth#&$ro$ane.
First sort out the carbon skeleton. 't#s a three carbon chain with no double bonds and a methyl group on
the second carbon atom.
5raw the bromine atom which is also on the second carbon.
And finally put the hydrogen atoms in.
If you had to name this yourself:
3otice that the whole of the hydrocarbon part of the name is written together $ as methylpropane $ before
you start adding anything else on to the name.
Example 2: -rite the structural formula for ,%iodo%)%eth#&$ent%'%ene.
This time the longest chain has , carbons (pent!, but has a double bond starting on the number * carbon.
There is also a methyl group on the number carbon.
3ow draw the iodine on the number ) carbon.
=iving a final structure0
Note* %ou could e<ually well draw this molecule the other way round, but normally where you have, say,
)$bromo$something, you tend to write the bromine (or other halogen! on the right$hand end of the
structure.
A&coho&!
All alcohols contain an $:/ group. This is shown in a name by the ending ol.
Example 1: -rite the structural formula for ethano&.
This is a one carbon chain with no carbon$carbon double bond (obviously(!. The ol ending shows it#s an
alcohol and so contains an $:/ group.
Example 2: -rite the structural formula for '%eth#&$ro$an%,%o&.
The carbon skeleton is a carbon chain with no carbon$carbon double bonds, but a methyl group on the
number * carbon.
The $:/ group is attached to the number ) carbon.
The structure is therefore0
Example 3: -rite the structural formula for ethane%,('%dio&.
This is a two carbon chain with no double bond. The diol shows 2 $:/ groups, one on each carbon atom.
Note* There#s no particular significance in the fact that this formula has the carbon chain drawn vertically.
'f you draw it hori6ontally, unless you stretch the carbon$carbon bond a lot, the $:/ groups look very
s<uashed together. 5rawing it vertically makes it look tidier(
A&deh#de!
All aldehydes contain the group0
'f you are going to write this in a condensed form, you write it as $./: $ never as $.:/, because that
looks like an alcohol.
The names of aldehydes end in al.
Example 1: -rite the structural formula for $ro$ana&.
This is a carbon chain with no carbon$carbon double bonds. The al ending shows the presence of the
$./: group. The carbon in that group counts as one of the chain.
Example 2: -rite the structural formula for '%eth#&$entana&.
This time there are , carbons in the longest chain, including the one in the $./: group. There aren#t any
carbon$carbon double bonds. A methyl group is attached to the number * carbon. 3otice that in
aldehydes, the carbon in the $./: group is always counted as the number ) carbon.
-etone!
9etones contain a carbon$oxygen double bond ;ust like aldehydes, but this time it#s in the middle of a
carbon chain. There isn#t a hydrogen atom attached to the group as there is in aldehydes.
9etones are shown by the ending one.
Example 1: -rite the structural formula for $ro$anone.
This is a carbon chain with no carbon$carbon double bond. The carbon$oxygen double bond has to be in
the middle of the chain and so must be on the number * carbon.
9etones are often written in this way to emphasise the carbon$oxygen double bond.
Example 2: -rite the structural formula for $entan%)%one.
This time the position of the carbon$oxygen double bond has to be stated because there is more than one
possibility. 't#s on the third carbon of a , carbon chain with no carbon$carbon double bonds. 'f it was on
the second carbon, it would be pentan$*$one.
This could e<ually well be written0