Alkohol

Alkohol

USES OF ALCOHOLS
Uses of ethanol
Drinks
The "alcohol" in alcoholic drinks is simply ethanol.
Industrial methylated spirits (meths)
Ethanol is usually sold as industrial methylated spirits which is
ethanol with a small quantity of methanol added and possibly
some colour. Methanol is poisonous, and so the industrial
methylated spirits is unfit to drink.
As a fuel
Ethanol burns to give carbon dioxide and water and can be used as
a fuel in its own right, or in mixtures with petrol (gasoline).
"Gasohol" is a petrol / ethanol mixture containing about 10 20% ethanol.
As a solvent
Ethanol is widely used as a solvent. It is relatively safe, and can be
used to dissolve many organic compounds which are insoluble
in water. It is used, for example, in many perfumes and
cosmetics.

ALKOHOL
Uses of methanol
As a fuel
As an industrial feedstock
Most methanol is used to make other things - for example, methanal
(formaldehyde), ethanoic acid, and methyl esters of various
acids. In most cases, these are in turn converted into further
products.
Uses of propan-2-ol
Propan-2-ol is widely used in an amazing number of different
situations as a solvent.

INTRODUCING ALKANES AND CYCLOALKANES

Physical Properties
Boiling Points

The facts
The boiling points shown are all for the "straight chain" isomers where there are more than one.
Notice that the first four alkanes are gases at room temperature. Solids don't start to appear
until about C17H36. You can't be more precise than that because each isomer has a different
melting and boiling point. By the time you get 17 carbons into an alkane, there are
unbelievable numbers of isomers! Cycloalkanes have boiling points which are about 10 - 20
K higher than the corresponding straight chain alkane.

Explanations

There isn't much electronegativity difference between carbon and hydrogen, so there is hardly
any bond polarity. The molecules themselves also have very little polarity. A totally
symmetrical molecule like methane is completely non-polar. This means that the only
attractions between one molecule and its neighbours will be Van der Waals dispersion
forces. These will be very small for a molecule like methane, but will increase as the
molecules get bigger. That's why the boiling points of the alkanes increase with molecular
size.

INTRODUCING ALKANES AND CYCLOALKANES

Where you have isomers, the more branched the chain, the lower the boiling point
tends
to be. Van der Waals dispersion forces are smaller for shorter molecules, and only
operate over very short distances between one molecule and its neighbours. It is
more
difficult for short fat molecules (with lots of branching) to lie as close together as
long thin
ones.
For example, the boiling points of the three isomers of C 5H12 are: boiling point (K)
of pentane, 309.22; methylbutane, 301.02; 2-dimethylpropane, 282.6. The
slightly higher boiling points for the cycloalkanes are presumably because the
molecules can get closer together because the ring structure makes them
tidier and less "wriggly"!

Solubility
Solubility
The facts
What follows applies equally to alkanes and cycloalkanes. Alkanes are virtually
insoluble in water, but dissolve in organic solvents. The liquid alkanes are
good solvents for many other covalent compounds.
Explanations
Solubility in water
When a molecular substance dissolves in water, you have to
break the intermolecular forces within the substance. In the case of the

alkanes, these are Van der Waals dispersion forces.

break the intermolecular forces in the water so that the substance can fit

between the water molecules. In water the main intermolecular attractions are
hydrogen bonds.
Breaking either of these attractions costs energy, although the amount of energy
to break the Van der Waals dispersion forces in something like methane is
pretty negligible. That isn't true of the hydrogen bonds in water, though.
As something of a simplification, a substance will dissolve if there is enough
energy released when new bonds are made between the substance and the
water to make up for what is used in breaking the original attractions.
The only new attractions between the alkane and water molecules are Van der
Waals. These don't release anything like enough energy to compensate for
what you need to break the hydrogen bonds in water. The alkane doesn't
dissolve.

Solubility
Solubility in organic solvents
In most organic solvents, the main forces of attraction between the solvent molecules
are Van der Waals - either dispersion forces or dipole-dipole attractions.
That means that when an alkane dissolves in an organic solvent, you are breaking Van
der Waals forces and replacing them by new Van der Waals forces. The two
processes more or less cancel each other out energetically - so there isn't any
barrier to solubility.

Chemical Reactivity
Alkanes
Alkanes contain strong carbon-carbon single bonds and strong carbon-hydrogen
bonds. The carbon-hydrogen bonds are only very slightly polar and so there aren't
any bits of the molecules which carry any significant amount of positive or
negative charge which other things might be attracted to.
The net effect is that alkanes have a fairly restricted set of reactions.
You can
burn them - destroying the whole molecule;

react them with some of the halogens, breaking carbon-hydrogen bonds;

crack them, breaking carbon-carbon bonds.

These reactions are all covered on separate pages if you go to the alkanes menu (see
below).
Cycloalkanes
Cycloalkanes are very similar to the alkanes in reactivity, except for the very small
ones - especially cyclopropane. Cyclopropane is much more reactive than you
would expect.
The reason has to do with the bond angles in the ring. Normally, when carbon forms
four single bonds, the bond angles are about 109.5. In cyclopropane, they are 60.
With the electron pairs this close together, there is a lot of repulsion between the
bonding pairs joining the carbon atoms. That makes the bonds easier to break.

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,
3). 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 atoms
You will need to remember the codes for the number of carbon
atoms in a chain up to 6 carbons. There is no easy way around
this - you have got to learn them. If you don't do this properly,
you won't be able to name anything!
codeno of carbons; meth, 1;eth, 2; prop, 3; but, 4; pent, 5; hex, 6

THE NAMES OF AROMATIC COMPOUNDS

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.
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

the name is based on benzene

(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.

the name is based on phenyl

phenylamine

Phenylamine is a primary amine and contains the -NH 2 group attached to a benzene
ring. The old name for phenylamine is aniline, and you could also reasonably call it
aminobenzene.

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 one ending 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.

phenol

Phenol has an -OH group attached to a benzene ring and so has a formula C 6H5OH.

Aromatic compounds with more

than one group attached to the
benzene
Substituting chlorine
atomsring
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.

Aromatic compounds with more

than one group attached to the
benzene ring
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. 2,4,6trichlorophenol is the familiar antiseptic TCP.

methyl 3-nitrobenzoate

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, NO 2, 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.