Grade 10 Introduction to Organic Chemistry Organic Chemistry is that branch of Chemistry that deals with carbon compounds (except for CO2, CO and CO32- compounds, which are considered to be Inorganic compounds). While all Organic compounds contain carbon, hydrogen is usually found as well, with oxygen, nitrogen, sulphur and halogens in many cases. With its four valence electrons, carbon has unique bonding abilities. Each carbon atom can form 4 covalent bonds with other atoms. These include other carbon atoms, hydrogen, oxygen, halogens, sulphur, etc.. The molecules (always covalently bonded) often consist of long carbon chains, and branches often occur. The atoms attached to carbon sometimes lie in the same plane, but generally the molecules are three dimensional. We will, however, depict them as two dimensional structures, using Couper diagrams, while bearing in mind that the diagrams actually represent three dimensional structures. C E.g.: C C C C C C C C C (The H atoms have not been shown here, but usually they must be shown.) The Aliphatic Compounds These are hydrocarbons with mainly open chain structures. They appear in three main ‘families’, the properties of which are determined to a large extent by the type of bond (called a functional group) found between carbon atoms: Functional group Single bonds: ALKANES C C Double bonds: ALKENES C C Triple bonds: ALKYNES C C 2 The Alkanes The alkanes form a homologous series with the general formula CnH2n+2 where n is the number of C atoms in a molecule. The name of each member of the series has the suffix –ane, while the prefix is determined by the number of C atoms: n 1 2 3 4 5 6 7 8 9 10 Formula CH4 C2H6 C3H8 C4H10 C5H12 C6H14 C7H16 C8H18 C9H20 C10H22 Name Methane Ethane Propane Butane Pentane Hexane Heptane Octane Nonane Decane Phase at room temp. Gas Gas Gas Gas Liquid Liquid Liquid Liquid Liquid Liquid Alkanes with 17 or more C atoms are waxy solids at room temperature. Note that only single covalent bonds appear in the alkanes. Such molecules are called saturated, which means that the maximum number of atoms are bonded to each C atom. Alkanes with branched chain structures Branches consist of alkyl groups, which are alkanes with one fewer H atom than usual: CH3 C2H5 C3H7 methyl ethyl propyl etc. To name the alkane according to the IUPAC naming system, follow the steps outlined below: 1. Choose the longest continuous C chain. 2. Number the chain so that the first branch appears at the C atom with the lowest number. 3. The total number of C atoms in the longest chain determines the name of the alkane. 4. The branches are named in alphabetical order (e.g. ethyl before methyl), with the number of its position in the chain given before the alkyl name, e.g. 2-methylbutane. There must be no gap between the alkyl and alkane names. If two of the same alkyl group appear, the prefix di- is used, e.g. dimethyl. For 3, use tri-, and for 4 use tetra-. 3 Examples: C 1. C C C C C 2-methylpentane C 2. C C C 2,2-dimethylbutane C C C 3. C C C C 2,3-dimethylbutane C The examples above are called structural isomers. This means that they are molecules that have the same molecular formula (C6H14 in each case), but different structural formulae. Isomers have different physical properties, like boiling points and melting points. Write structural formulae for the isomers of pentane, and name each one: 4 The Alkenes This series of compounds is unsatutated, since double covalent bonds appear between two C atoms. The general formula is CnH2n. The suffix –ene is added to the same prefixes as we use for the alkanes: n 2 3 4 5 6 7 Formula C2H4 C3H6 C4H8 C5H10 C6H12 C7H14 Name Ethene Propene Butene Pentene Hexene Heptene Phase at room temp. Gas Gas Gas Liquid Liquid Liquid IUPAC names The same procedure is followed as for the alkanes, but the longest chain must contain the double bond and be numbered from the end closest to the double bond. The position of the double bond is shown by the lower number of its two C atoms. E.g.: C C C C C C C but-1-ene but-2-ene C C C C C C C 3-methylpent-2-ene C C 3,4-dimethylpent-2-ene C C C C C 5 The Alkynes The alkynes are also unsaturated, with a triple covalent bond between two C atoms. The general formula is CnH2n-2. Naming a molecule follows the same route as that for alkenes, with the suffix –yne used. E.g.: C ethyne C propyne C C C C C C C but-1-yne C C C C but-2-yne