What is organic chemistry?

Organic chemistry is the chemistry of the compounds of CARBON, which, in combination with many other elements (in particular H, N, O, S, P and the halogens) form over 5 000 000 compounds. Many of these compounds are of immense importance, as the list below shows:

Fuels Solvents Explosives Detergents Plastics, synthetic fibres Rubber Wool, cotton, natural fibres

Insecticides, pesticides Animal toxins, plant poisons Vitamins, hormones Synthetic pharmaceuticals Antibiotics Dyestuffs Foodstuffs, flavourings and preservatives

Apart from water, living things are largely made up of organic compounds, notably proteins, fats, carbohydrates and nucleic acids. The study of these compounds, and the role they play in all life processes, is a special area of study called BIOCHEMISTRY. Historical note: Wohler and the synthesis of urea.

Structure of organic compounds:

Organic compounds tend to be built according to a general scheme as follows: The carbon atoms form a "skeleton", in this example, shown on the right, a chain of six C atoms. Hydrogen atoms are the most common atoms found linked to carbon atoms. In HYDROCARBONS, the major constituents of petroleum, they are the only atoms found linked to carbon. One or more reactive chemical groups of atoms (known as FUNCTIONAL GROUPS) are attached to the carbon chain (in the case illustrated above, the functional group is O-H). Hydrogen atoms are bound to the carbon skeleton by means of covalent bonds. There are other ways of representing the structure of organic compounds:

represents, in condensed form, the same molecule, without all the bonds being shown.

IMPORTANT NOTICE FOR SOUTH AFRICAN LEARNERS: The marking system used by the Department of Education requires that all the bonds in the molecule be explicitly shown. You will lose marks (unreasonably, we feel) if you write down a structural formula for a molecule in condensed form, as is shown above on the left (as organic chemists do) instead of the way shown on the right. So, play it safe! Sometimes only bonds are shown, or one uses models known as BALL-ANDSTICK or FILLED (the colours black, red and white represent atoms of carbon, oxygen and hydrogen respectively):

The arrangement in space of all the atoms of a molecule is called the STRUCTURE of the molecule. The complexity of the structure will clearly depend on the size of the molecule.

For example, the structure of the particular substance with formula C6H14 might be described in terms of a STRUCTURAL FORMULA such as the one shown on the left (expanded form with all atoms and bonds shown).

or, as shown here on the right, in condensed form.

As shown above, carbon skeletons are immensely varied: they may consist of straight chains of various lengths, branched chains, rings of various sizes and combinations of these.

Why is it that carbon can form stable, extended chains? (Click here for a discussion)

Functional groups:
FUNCTIONAL GROUPS are groups of atoms that have special chemical properties and which define the chemistry of an organic compound. The following are common functional groups: Functional group (none) C=C CC Found in alkanes alkenes alkynes

arenes R is hydrogen or a group of atoms derived from alkanes or other hydrocarbons C-X (X is a halogen atom) C-O-H haloalkanes alkanols aldehydes ketones carboxylic acids esters ethers C-N amines amides

Isomerism:
Have a good look at the two structural formulae shown below. Both of these are structural formulae applying to molecules with molecular formulae C6H14.

These two molecules are said to be ISOMERS. Isomers are compounds which have the same molecular formula, but different structural formulae. In other words, although the atoms, both in number and in type, are the same, they are arranged differently in space. Isomers normally also differ in their chemical and physical properties. (See the condensed structural formulae ) Isomers do not have to belong to the same class of organic compounds. For example, the compounds whose structural formulae are shown below, are isomers. The one on the left is aCARBOXYLIC ACID, while the one on the right is an ESTER:

See the condensed structural formulae ( molecular formula C5H10O2.

) and verify that they both have the

Additional questions

Alkanes:
Alkanes are hydrocarbons (compounds containg only C and H) that have single covalent bonds joining the carbon atoms. The carbon atoms form open chains, which may have branches. The molecular formula of all alkanes fits the expression CnH2n+2, where n is the number of carbon atoms.

Check that the formula is C6H14!

Alkanes are of tremendous importance, as the are the major constituents of petroleum.

Alkenes:
Alkenes are hydrocarbons (compounds containg only C and H) that have one or more C=C double bonds (two C atoms are linked by 4 shared electrons). The general formula is CnH2n, which is twohydrogen atoms less than the corresponding alkane.

Alkenes are said to be UNSATURATED, (since they do not have their full complement of hydrogen atoms).

Alkynes:
These are hydrocarbons (compounds containg only C and H) that have one or more CC triple bonds (two C atoms are joined by 6 shared electrons). The molecular formula fits the formula CnH2n-2and has therefore four hydrogen atoms less than the corresponding alkane.

Alkynes are said to be UNSATURATED, (since they do not have their full complement of hydrogen atoms). The simplest alkyne, HCCH, is commonly known as acetylene.

Arenes:

Arenes are hydrocarbons that are built on the carbon skeleton of BENZENE, C6H6, a hydrocarbon whose structure is shown above in three different representations. The two structures on the right are simplified structural formulae, the one on the extreme right being the one that is most commonly used nowadays ( ). Arenes all contain what is known as the BENZENE RING and are also known as AROMATIC HYDROCARBONS. They encompass a huge variety of organic compounds, some of which are shown below.

In turn, arenes provide us with a huge variety of carbon skeletons that can carry functional groups.

Haloalkanes:
If one or more hydrogen atoms of an alkane is replaced by a halogen atom (F, Cl, Br or I, chemists use the term SUBSTITUTION for this process), the compound is a HALOALKANE.

Alkanols:
These compounds arise when one or more hydrogen atoms of an alkane are substituted by the -O-H (HYDROXYL) functional group.

Alkanols are classified into primary, secondary, and tertiary alkanols, depending on the number of hydrogen atoms that are bonded to the carbon atom that is attached to the hydroxyl (-OH) functional group (see the examples in the table below): Alkanol class Structural formula ethanol Primary alkanol methanol Name

Secondary alkanol

propan-2-ol

Tertiary alkanol

2-methyl-propan-2-ol

Looking at the table above, we see that

Primary alkanols have the hydroxyl group attached to a carbon atom that is itself attached to only one other carbon atom. The simplest of all alkanols, methanol, is an exception in that it has three hydrogen atoms attached to the carbon atom that bears the hydroxyl group. Secondary alkanols have the hydroxyl group attached to a carbon atom that is itself attached to two other carbon atoms. Tertiary alkanols have the hydroxyl group attached to a carbon atom that is itself attached to three other carbon atoms.

Carboxylic acids:
These are compounds that have the carboxyl -COOH functional group, whose structure contains a C=O bond:

Esters:
Esters are compounds that have the CO-O-C functional group. This group, derived from the carboxyl group, also contains a C=O double bond:

Ethers:
Ethers are compounds where an oxygen atom is joined to two carbon atoms by single bonds. They are isomeric with alkanols with the same number of carbon atoms.

Ketones and aldehydes

Both ketones and aldehydes have the >C=O (carbonyl) group. In ketones, that group is "sandwiched" between two carbon atoms. This means that the simplest ketone must have 3 carbon atoms. In aldehydes, the >CO group is attached to one carbon atom and one hydrogen atom. The exception is formaldehyde, HCOH, where the carbonyl group is attached to two hydrogen atoms. The examples shown below should make this clear.

Amines:

AMINES are compounds that are derived from ammonia. They all have at least one carbon atom attached to the nitrogen atom. This carbon atom is not bound to oxygen (see under amides, below). If only one carbon atom is attached to the nitrogen atom, the amine is said to be PRIMARY. If the nitrogen atom is attached to two carbon atoms, it is a SECONDARY amine, and with three carbon atoms, it is a TERTIARY amine.

Amines can be considered to be hydrocarbon derivatives of ammonia. As such, they behave as bases.

Amides:
AMIDES are compounds that are derived from ammonia or amines AND a carboxylic acid. They all have the >C=O (carbonyl) group of the acid linked to the nitrogen atom. Amides are classified as primary amides, secondary amides, and tertiary amides, depending on the number of hydrogen atoms bonded to the nitrogen atom (see the examples in the table below): Amide class Primary amide Structural formula ethanamide Name

Secondary amide

N-methylethanamide

Tertiary amide

NN-dimethylethanamide

Looking at the table above, we see that

Primary amides have 2 hydrogen atoms bonded to the nitrogen atom. Secondary amides have 1 hydrogen atom bonded to the nitrogen atom. Tertiary amides do not have a hydrogen atom bonded to the nitrogen atom.