Chemistry Handout 18 REF #: 018

Reactions of Carbon Compounds

Alkanes : General Formula: CnH2n+2

Alkanes are saturated hydrocarbons. Saturated compounds contain only single covalent bonds between carbon atoms.
No more hydrogen atom can be added to the molecule. Straight and branched- chain isomers occur in alkanes with four
or more carbon atoms. Alkanes are colourless volatile compounds. The boiling point of the compounds rises steadily as
the relative molecular mass increases. Because alkanes are saturated, they are relatively unreactive.

1. Combustion
If ignited, alkanes burn in an excess of air (or an excess of oxygen) with clean, blue, non-smoky flames forming carbon
dioxide, water and heat. The reaction is described as a complete combustion reaction and the reaction is highly
exothermic.
Equation: Alkane + Oxygen  Carbon dioxide + Water + Heat
However, if the supply of air or oxygen is insufficient, the alkane molecules are not completely oxidized to carbon
dioxide and water. Other products such as carbon monoxide and carbon and even hydrogen might be formed.

2. Substitution
A substitution reaction is one in which one or more hydrogen atoms in a saturated compound are replaced by some
other atom or group of atoms.
Halogenation
Alkanes undergo substitution reactions with the halogens (especially chlorine) in the presence of bright light, usually
sunlight.
The substitution reaction gives a mixture of organic products and hydrogen chloride gas. The organic products are
known as halogenoalkanes and the number of atoms replaced in the reaction depends on the relative quantities of
alkane and halogen used. No reaction occurs in the dark; in bright light, the reaction is explosive; in diffused light
substitution occurs in stages, one chlorine atom at a time.
Equation: Alkane + Halogen  Halogenoalkane
You can show that substitution is taking place by reacting the HCl (g) produced with concentrated ammonia. Dense
white fumes of ammonium chloride will be formed:
HCl (g) + NH3 (g)  NH4Cl (s)

Uses of Alkanes

1. Alkanes are used mainly as fuels- examples are LPG and natural gas. This is because alkanes produce a lot of heat when
they burn (reactions are highly exothermic) and the flames are clean (do not produce polluting smoke). Other properties
of a good fuel are:
 They ignite easily but not spontaneously under normal  They are inexpensive
conditions  They are safe to use
 They burn well but not explosively  They are easy to store and transport.
 They have low smoke and ash content
2. Halogenoalkanes are used as:
 Solvents- examples are trichloromethane and tetrachloromethane

A. BAKSH
 Chemistry Handout 18 REF #: 018
 Anaesthetics- halothane, for example, is a halogenoalkane which is widely used in hospitals. (It contains fluorine,
bromine and chlorine). Chloromethane is used for local anaesthesia by spraying on the skin.
 Pesticide

Alkenes: General Formula: CnH2n

Alkenes are unsaturated hydrocarbons. Unsaturated compounds contain double and or triple covalent bonds between
two or more carbon atoms. Alkenes have one double bond between one pair of carbon atoms. Straight and branched-
chain isomers occur in alkenes with four or more carbon atoms. Also, the position of the double bond can vary to
produce further isomers. Alkenes are colourless volatile compounds. Alkenes are more reactive than alkanes because
one bond of the double bond is weaker and is easily broken. The double bond allows atoms or group of atoms to add to
the molecule.

1. Combustion
Like Alkanes, Alkenes burn in excess oxygen, producing carbon dioxide and steam.
Equation: Alkene + Oxygen  Carbon dioxide + Water + Heat
When the gas burns in air, there is insufficient oxygen available to in the flame and so complete combustion is not
achieved. The flame is noticeably smoky yellow because it contains particles of unburnt carbon which glows brightly in
the flame (the unburnt carbon is due to the high proportion of carbon in the alkene molecule)

2. Addition
An addition reaction is one in which an unsaturated compound reacts with a given reagent to form a saturated
compound as the only product. The reagent adds across the double bond. Addition reactions happen much more easily
than substitution reactions.
Halogenation
Halogens add across the double bond without displacing any hydrogen atoms. The unsaturated alkene becomes a
saturated alkane.
Equation: Alkene + halogen  halogenoalkane
Hydration
Hydration is the addition of a water molecule across a double bond in an unsaturated molecule. Water adds across the
double bond of the alkane and an alcohol is produced.
Equation: Alkene + Water  Alcohol
Hydration can be achieved both directly and indirectly.
The direct hydration of ethene is used to produce ethanol commercially. Ethene is compressed to about 70 atm, mixed
with water and passed through a furnace. The heated mixture is then passed over a phosphoric acid catalyst at a
temperature of 300 0C. Ethanol is formed and the mixture of gases, ethanol vapour plus uncombined ethene and steam
is then passed through a condenser where ethanol vapour and steam are condensed and drawn off. Unreacted ethene
can then be recycled.

Hydrogenation
Hydrogen adds to alkenes in the presence of finely divided nickel, which serves as a catalyst.
The reaction results in the formation of the corresponding alkane.
Equation: Alkene + Hydrogen  Alkane

Uses of Alkenes
A. BAKSH
 Chemistry Handout 18 REF #: 018
Alkenes are used in the manufacture of many other chemicals owing to their readiness to undergo addition reactions.
Eg. To manufacture ethanol and other alcohols, vinylcholride (chloroethene), polychloroethene (polyvinylchloride, PVC),
polythene, benzene, ethane-1,2-diol (antifreeze), phenylethene (styrene), polyphenylethene (polystyrene).

Cracking
- Can be done in the presence of heat alone
- Or in the presence of heat and a catalyst
- Heat makes the hydrocarbon molecules vibrate to such an extent that the carbon-carbon bonds break at certain points.

Reforming

- Straight chain hydrocarbons are broken up and then reassembled into branched hydrocarbons. Eg: the conversion of low
grade gasoline to high grade gasoline

Gasoline with a high proportion of straight chain alkanes has a ‘low octane’ rating because it causes knocking in the
engine. Knocking occurs when the fuel in the engine’s cylinders explodes too early. Knocking results in the overheating
of the engine and a loss of power and as well causing the ‘knocking noise’ and possibly damaging parts of the engine.

The Differences between Alkanes and Alkenes

The differences between alkanes and alkenes are based on the fact that:

1. Alkanes are saturated compounds, so they undergo substitution reactions. (Substitution reaction is the
characteristic equation for alkanes)
2. Alkenes are unsaturated compounds, so they undergo addition reactions. (Addition reaction is the characteristic
equation for alkenes)

Alkenes can therefore be told apart from alkanes by testing for the presence of unsaturation.

Test Observations Equation

Alkane Alkene
Add bromine vapour Slow Rapid decolourisation of bromine in dark or
decolourisation light- rapid addition occurs
of bromine in
light- slow
substitution
occurs
Add a solution of No colour Rapid decolourisation of bromine solution
bromine in water or change- no (rapid addition occurs)
tetrachloromethane reaction occurs
Add acidified No colour Rapid decolourisation of acidified potassium
potassium (VII) change- no manganite (VII) solution (rapid addition
manganite solution reaction occurs occurs)- Note that two hydroxyl groups are
added across the double bond, forming a di-
alcohol. The reaction is rapid and there is an
obvious colour change from deep purple to
a very pale pink.

A. BAKSH
 Chemistry Handout 18 REF #: 018
Alcohols, Alkanoic Acids and Esters
Alcohols (Alkanols) : General Formula: CnH2n+1OH or R-OH, where R represents an alkyl group and the hydroxyl (-
OH) group is the functional group.

The properties of alcohols are determined by the hydroxyl (-OH) group. Owing to the presence of this group, alcohols
(especially the smaller ones) are soluble in water. As the size of the hydrocarbon chain increases, the solubility of the
alcohol in water decreases. Alcohols are also less volatile (have higher boiling points) than their corresponding alkanes.
At room temperature C1 to C12 are liquids, the rest are solids. As the length of the carbon chain increases, volatility also
decreases.

Straight and branched-chain isomers occur in alcohols with four or more carbon atoms. Also the position of the
functional group can vary to produce further isomers.

Reactions of Alcohols/ Ethanol- Alcohols are chemically reactive. Ethanol and other alcohols undergo a number of
reactions based on the presence of the hydroxyl (-OH) functional group.

1. Combustion
Ethanol burns with a clean blue flame forming carbon dioxide, water and heat (the reaction is highly exothermic). The
alcohol mole contains some of the necessary oxygen so the flame contains no unreacted carbon. The reaction is described
as the complete combustion of alcohol.
Equation: Alcohol + Oxygen  Carbon Dioxide + Water + Heat

2. Reaction with sodium

The reaction of ethanol with sodium metal yields a salt of the metal (alkoxide) called sodium ethoxide and hydrogen gas.
Reaction: Alcohol + Metal  Alkoxide + Hydrogen gas

3. Dehydration
Ethanol is dehydrated to ethene by heating it to about 1700C in the presence of concentrated sulphuric acid, or by passing
ethanol vapour over activated aluminium oxide heated to 4500C. The reaction is described as a dehydration. The water is
lost across two adjacent carbon atoms in the alcohol. This results in the formation of a double bond between the two
carbon atoms.
Equation: Alcohol  Alkene + Water conc. H2SO4 1700C.

4. Oxidation
Ethanol is oxidized to ethanoic acid by heating with powerful oxidizing agents such as acidified potassium dichromate (VI)
or acidified potassium manganite (VII). In the reaction, an intermediate, ethanal (an aldehyde) is formed.
During the reaction, the mixture changes colour from purple to colourless if potassium manganite is used and from
orange to green if potassium dichromate is used.
Reaction: Alcohol + [O]  carboxylic acid

5. Conversion to Ester
Ethanol reacts with carboxylic acids to form an ester and water. The reaction is reversible
Equation: Alcohol + Carboxylic Acid ↔Ester + Water

A. BAKSH