The aromatics are a fourth group,

Hydrocarbon

Formula

aromatic

CnHn

The only member of the aromatic group we will spend time on is benzene, C6H6. It looks like,

Functional Group

Ball-and-stick

Lewis Structure

aromatic (benzene)

Recognizing the aromatic group consists of finding the six-membered ring of carbon atoms. Although the ball-and-stick model above does not clearly show it the benzene ring is planar.

Functional Group

Ball-and-stick

Lewis Structure

aromatic (benzene)

Benzene is a liquid at room temperature and is an important solvent because organic compounds are more soluble in it than in water.

Lets look at some compounds that contain the aromatic benzene (benzyl) group.

Compound

Ball-and-Stick

Lewis Structure

Toluene (methyl benzene)

Phenol

Styrene

Phenol is interesting as it has an alcohol functional group as well as the aromatic functional group.

Naming aromatic compounds isn't quite so straightforward as naming chain

compounds. Often, more than one name is acceptable and it's not uncommon to
find the old names still in use as well.

Background
The benzene ring
All aromatic compounds are based on benzene, C6H6, which has a ring of six
carbon atoms and has the symbol:

Each corner of the hexagon has a carbon atom with a hydrogen attached.

Note: If you don't understand this structure, it is explained in full

in two pages on the structure of benzene elsewhere in this site.
Following this link could well take you some time!

The phenyl group

Remember that you get a methyl group, CH3, by removing a hydrogen from
methane, CH4.
You get a phenyl group, C6H5, by removing a hydrogen from a benzene ring,
C6H6. Like a methyl or an ethyl group, a phenyl group is always attached to
something else.

Aromatic compounds with only one group attached to the benzene ring
Cases where the name is based on benzene
chlorobenzene
This is a simple example of a halogen attached to the benzene ring. The name is
self-obvious.

The simplified formula for this is C6H5Cl. You could therefore (although you never
do!) call it phenyl chloride. Whenever you draw a benzene ring with one other
thing attached to it, you are in fact drawing a phenyl group. In order to attach
something else, you have to remove one of the existing hydrogen atoms, and so
automatically make a phenyl group.
nitrobenzene
The nitro group, NO2, is attached to a benzene ring.

The simplified formula for this is C6H5NO2.

methylbenzene

Another obvious name - the benzene ring has a methyl group attached. Other
alkyl side-chains would be named similarly - for example, ethylbenzene. The old
name for methylbenzene is toluene, and you may still meet that.

The simplified formula for this is C6H5CH3.

(chloromethyl)benzene
A variant on this which you may need to know about is where one of the
hydrogens on the CH3 group is replaced by a chlorine atom. Notice the brackets
around the (chloromethyl) in the name. This is so that you are sure that the
chlorine is part of the methyl group and not somewhere else on the ring.

If more than one of the hydrogens had been replaced by chlorine, the names
would be (dichloromethyl)benzene or (trichloromethyl)benzene. Again, notice the
importance of the brackets in showing that the chlorines are part of the side
group and not directly attached to the ring.
benzoic acid (benzenecarboxylic acid)
Benzoic acid is the older name, but is still in common use - it's a lot easier to say
and write than the modern alternative! Whatever you call it, it has a carboxylic
acid group, -COOH, attached to the benzene ring.

Cases where the name is based on phenyl

Remember that the phenyl group is a benzene ring minus a hydrogen atom C6H5. If you draw a benzene ring with one group attached, you have drawn a
phenyl group.
phenylamine

Phenylamine is a primary amine and contains the -NH2 group attached to a

benzene ring.

The old name for phenylamine is aniline, and you could also reasonably call it
aminobenzene. Phenylamine is what it is most commonly for UK-based exam
purposes.

Note: In all cases where there is some possibility of alternative

names, you need to know what your examiners are likely to call a
particular compound. Refer to yoursyllabus and recent exam
papers. If you are working to a UK-based syllabus for 16 - 8 year
olds, and haven't got these, follow this link to find out how to get
hold of them.

phenylethene
This is an ethene molecule with a phenyl group attached. Ethene is a two carbon
chain with a carbon-carbon double bond. Phenylethene is therefore:

The old name for phenylethene is styrene - the monomer from which polystyrene
is made.
phenylethanone
This is a slightly awkward name - take it to pieces. It consists of a two carbon
chain with no carbon-carbon double bond. The oneending shows that it is a
ketone, and so has a C=O group somewhere in the middle. Attached to the
carbon chain is a phenyl group. Putting that together gives:

phenyl ethanoate
This is an ester based on ethanoic acid. The hydrogen atom in the -COOH group
has been replaced by a phenyl group.

Note: If you aren't happy about naming esters, follow this link
before you go on.

phenol
Phenol has an -OH group attached to a benzene ring and so has a formula
C6H5OH.

Aromatic compounds with more than one group attached to the benzene
ring
Numbering the ring
Any group already attached to the ring is given the number 1 position. Where you
draw it on the ring (at the top or in any other position) doesn't matter - that's just
a question of rotating the molecule a bit. It's much easier, though, to get in the
habit of drawing your main group at the top.
The other ring positions are then numbered from 2 to 6. You can number them
either clockwise or anti-clockwise. As with chain compounds, you number the
ring so that the name you end up with has the smallest possible numbers in it.
Examples will make this clear.
Some simple examples
Substituting chlorine atoms on the ring

Look at these compounds:

All of these are based on methylbenzene and so the methyl group is given the
number 1 position on the ring.
Why is it 2-chloromethylbenzene rather than 6-chloromethylbenzene? The ring is
numbered clockwise in this case because that produces a 2- in the name rather
than a 6-. 2 is smaller than 6.

Warning! You will find all sorts of variations on this depending on

the age of the book you look it up in, and where it was published.
What I have described above isn't in strict accordance with the
most modern interpretation of the IUPAC recommendations for
naming organic compounds.
The names should actually be 1-chloro-2-methylbenzene, 1chloro-3-methylbenzene, and so on. The substituted groups are
named in alphabetical order, and the "1" position is assigned to
the first of these - rather than to the more logical methyl group.
This produces some silly inconsistencies. For example, if you had
the exactly equivalent compounds containing nitro groups in place
of the chlorines, the names would change completely, to 1-methyl2-nitrobenzene, 1-methyl-3-nitrobenzene, etc. In this case, the
normal practice of naming the hydrocarbon first, and then
attaching other things to it has been completely wrecked.
Do you need to worry about this? NO! It is extremely unlikely that
you would ever be asked to name these in an exam, and it is
always easy to write a structure from one of these names however illogical it may be! There is a simple rule for exam
purposes. Unless you are specifically asked for the name of
anything remotely complicated, don't give it. As long as you have
got the structure right, that's all that matters.

2-hydroxybenzoic acid

This might also be called 2-hydroxybenzenecarboxylic acid. There is a -COOH

group attached to the ring and, because the name is based on benzoic acid, that
group is assigned the number 1 position. Next door to it in the 2 position is a
hydroxy group, -OH.

benzene-1,4-dicarboxylic acid
The di shows that there are two carboxylic acid groups, -COOH, one of them in
the 1 position and the other opposite it in the 4 position.

2,4,6-trichlorophenol
This is based on phenol - with an -OH group attached in the number 1 position
on the ring. There are 3 chlorine atoms substituted onto the ring in the 2, 4 and 6
positions.

methyl 3-nitrobenzoate
This is a name you might come across as a part of a practical exercise in
nitrating benzene rings. It's included partly for that reason, and partly because it
is a relatively complicated name to finish with!
The structure of the name shows that it is an ester. You can tell that from
the oate ending, and the methyl group floating separately from the rest of the
name at the beginning.
The ester is based on the acid, 3-nitrobenzoic acid - so start with that.
There will be a benzene ring with a -COOH group in the number 1 position and a
nitro group, NO2, in the 3 position. The -COOH group is modified to make an

ester by replacing the hydrogen of the -COOH group by a methyl group.

Methyl 3-nitrobenzoate is therefore: