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Organic Chemistry A huge variety of molecules, including most of the building-blocks for living systems, are based on carbon

with just a few other elements e.g. O, H, and N. This is possible because carbon forms 4 covalent bonds, so can be bonded to other atoms in many different configurations.

Formulae Because many different organic molecules can have the same molecular formula, we need different kinds of formulae to tell them apart.
The simplest is the displayed formula, which shows each atom and sticks for the bonds between them. e.g. C2H6O could be:

We can also use structural formulae, which group together the atoms in the molecule, carbon by carbon:

CH3CH2OH
ethanol

CH3OCH3
methoxymethane

Functional Groups Molecules with the same groups of atoms in them have similar chemical properties. We call this group of atoms a functional group. A family of molecules with the same functional group is called a homologous series. Each member of the family will differ from the other members by CH2These are the functional groups you need to know for GCSE Chemistry:

O C

C=C
alkene

-O-H
alcohol

O
ester
O H H H C C C C H H H H

carboxylic acid

Draw a ring around the functional group in each of these molecules, and identify them as alcohols, carboxylic acids, esters or alkenes: [answers at the end]
O H O H H H C C C C H H H H

H H H H C C C H H O H H

H H H C C O H H

H H C C H

O O H

H
H H C C H O H O C H H

H H C O H H

H H

H H C C C H H

O H H C C H O H H

C H C C H H C H H H

More about alcohols Recognise alcohols either by the -ol ending to the name, or the OH functional group in the molecule. first three in the homologous series are: methanol CH3OH ethanol CH3CH2OH propanol CH3CH2CH2OH

alcohols dissolve in water to form solutions with neutral pH


when sodium is added to alcohols, fizzing is seen as bubbles of hydrogen are produced. The sodium dissolves and a salt is formed.

2 CH3OH + 2 Na
methanol sodium

2 CH3ONa

H2
hydrogen

sodium methoxide

alcohols burn readily in air, making good fuels an alcohol + oxygen carbon dioxide + water

e.g.

2 CH3OH + 3 O2 C2H5OH + 3 O2 2 C3H7OH + 9 O2

2 CO2 + 4 H2O 2 CO2 + 3 H2O 6 CO2 + 8 H2O

alcohols are good solvents, lots of different substances will dissolve in alcohols this is one of the main industrial uses for alcohols made by reacting alkenes with steam.

ethanol is the main alcohol in alcoholic drinks, produced from plant sugars by fermentation with yeast.

alcohols can be oxidised to carboxylic acids, either by chemical oxidising agents such as sodium dichromate, or by microbial action.
this is why wine that has left open to the air tastes bad. The ethanol has been oxidised to ethanoic acid (vinegar).

More about carboxylic acids Recognise carboxylic acids either by the -oic acid ending to the name, or the COOH functional group in the molecule. first three in the homologous series are: methanoic acid HCOOH ethanoic acid CH3COOH propanoic acid CH3CH2COOH

carboxylic acids dissolve in water to form acidic solutions with pH less than 7.
carboxylic acids are weak acids because they do not ionise completely - only a few of the acid molecules break up in solution to produce the H+(aq) ions which are responsible for acidic behaviour. This makes them different from strong acids like hydrochloric acid or sulphuric acid which are fully ionised in solution. All the acid molecules split up to produce H+(aq) ions. How can we tell a weak acid from a strong acid ? When we compare two acids with the same concentration using Universal Indicator (or a pH probe), the strong acid will have a lower (more acidic) pH because the concentration of H+ ions will be greater.

When reactive metals such as magnesium react with a strong acid the fizzing will be more rapid and the metal will dissolve more quickly than when the metal reacts with a weak acid of the same concentration.

carboxylic acids react with carbonates. Carbon dioxide gas is given off.
The shells of eggs are mainly made of calcium carbonate. This can react with acids, e.g. we can dissolve the shell off an egg by soaking it in vinegar (ethanoic acid). Carboxylic acids react with hydrogencarbonates in the same way. Solid citric acid and solid sodium hydrogencarbonate can be mixed, and will react together when water is added. This causes the fizz in AlkaSeltzer.

More about esters Recognise esters either by the -yl -anoate form of the name, or the COO- functional group in the molecule. e.g. ethyl ethanoate CH3COOCH2CH3

H O H

H H H H

H C C O C C H
Esters are volatile compounds with distinctive smells and are used as flavourings and perfumes. Many fruits and flowers are natural sources of esters. Esters are formed by reacting a carboxylic acid with an alcohol in the presence of an acid catalyst. For example, ethyl ethanoate is the ester produced by reacting ethanoic acid with ethanol: ethanol + ethanoic acid ethyl ethanoate + water

Answers to identifying the functional groups:


O H O H H H C C C C H H H H

H H H H C C C H H O H H

O H H H C C O H H

H H H C C C C H H H H

H H C C H

O O H

carboxylic acid

alcohol

ester

carboxylic acid

H
H H C O H H

H H

H H C C C H H

H H C C H

O H O C H H

O H H C C H O H H

C H C C H H C H H H

alcohol

alkene

ester

alcohol

alkene