Discuss the properties and reaction of aromatic compounds
Properties of methyl benzene
Properties Density Methyl benzene relative density (water = 1) 0. 87 = less than in water the relative density (Air = 1) 3.14 = denser in air do not dissolve in water, but dissolve in organic solvent -95° C 111° C High flammable 4.89kPa 7
Solubility Melting point Boiling point Flammability Vapor pressure ph value
Properties of methyl benzene.
y It is immiscible with water y It burns in oxygen
C6H5CH3 + 9O2
7CO2 + 4H2O
As seen from the equation, a lot of oxygen is required. In air the combustion tends to be incomplete and results in a Smokey flame.
y Very slow reaction with bromine water - it
resists addition reactions.
Since methyl benzene doesn't react with bromine it cannot contain any C=C double bonds.
y It is transparent colorless liquid
Reactions for the methyl benzene
Reaction of methyl benzene
y Like any other hydrocarbons, benzene and
methylbenzene burn in a plentiful supply of oxygen to give carbon dioxide and water. y example:of methylbenzene
y However, for these hydrocarbons, combustion is
hardly ever complete, especially if they are burnt in air.
y As a general rule, the hydrogen in a
hydrocarbon tends to get what oxygen is available first, leaving the carbon to form carbon itself, or carbon monoxide, if there isn't enough oxygen to go round.
y Hydrogenation is an addition reaction in
which hydrogen atoms are added all the way around the benzene ring. A cycloalkane is formed. y For example:
y These reactions destroy the electron
delocalisation in the original benzene ring, because those electrons are being used to form bonds with the new hydrogen atoms. y The reactions are done using the same finely divided nickel catalyst that is used in hydrogenating alkenes and at similar temperatures (around 150°C), but the pressures used tend to be higher.
y With hot acidic KMnO4 :
y With acidic manganese or chromyl chloride (Etards
y All alkyl benzenes on oxidation with hot acidic
KMnO4 or Na2Cr2O7 form benzoic acid. The length of the side chain does not matter.
y Sulphonation involves replacing one of the
hydrogens on a benzene ring by the sulphonic acid group, -SO3H.
y Methylbenzene is more reactive than benzene
because of the tendency of the methyl group to "push" electrons towards the ring.
The main reaction are:
y The effect of this greater reactivity is that
methylbenzene will react with fuming sulphuric acid at 0°C, and with concentrated sulphuric acid if they are heated under reflux for about 5 minutes.
y As well as the effect on the rate of reaction,
with methylbenzene you also have to think about where the sulphonic acid group ends up on the ring relative to the methyl group.
y Methyl groups have a tendency to "direct" new
groups into the 2- and 4- positions on the ring (assuming the methyl group is in the 1- position). Methyl groups are said to be 2,4-directing. The origin of this directing effect is also beyond UK A level. y So you get a mixture which mainly consists of two isomers. Only about 5 - 10% of the 3- isomer is formed.
In the case of sulphonation, the exact proportion of the isomers formed depends on the temperature of the reaction. As the temperature increases, you get increasing proportions of the 4- isomer and less of the 2- isomer.
y This is because sulphonation is reversible.
The sulphonic acid group can fall off the ring again, and reattach somewhere else. y This tends to favour the formation of the most thermodynamically stable isomer. This interchange happens more at higher temperatures.
y The 4- isomer is more stable because
there is no cluttering in the molecule as there would be if the methyl group and sulphonic acid group were next door to each other.
Substitution of bromine