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HYDROCARBONS • Hydrocarbons are composed, as their name suggests mainly of carbon and hydrogen atoms, though some types have oxygen, nitrogen or sulphur atoms. • Hydrocarbons are divided into two groups, Aliphatics or Aromatics. Most hydrocarbons are aliphatics. Representing Hydrocarbon • There are four ways in which hydrocarbons can be represented. • 1. Chemical Formula We are used to using chemical formulas to represent compounds. Unfortunately, chemical formulas are not useful when dealing with organic molecules because the arrangement of the atoms within the molecule is important. This can be seen with the sugars glucose and fructose. Comparison of glucose and fructose • 2. Structural formulas are very useful and important in organic chemistry. A structural formula shows both the type and arrangement of the elements and all bonds. • 3. Condensed formulas show major bonds but normal C to H bonds are not drawn. • CH3CH2CH2CH2CH3 • 4. Line diagrams represent the molecule using lines. The end of a line means CH3 while a corner is CH2 ALKANES • Alkanes area class of HYDROCARBONS which contain only carbon and hydrogen. Two other terms which describe alkanes are saturated and paraffins. • Alkanes are SATURATED which means that each carbon is bonded to four other atoms through single covalent bonds. Hydrogen atoms usually occupy all available bonding positions after the carbons have bonded to each other. • PARAFFINS which is derived from a Latin word meaning "little activity", and means that the compounds are very unreactive. • The general structure is CnH2n+2 Two common alkanes Properties Physical Properties • Boiling points depend on chain length. The longer the chain the higher the boiling temperature • Non polar • Insoluble in water Chemical Reactivity • No functional groups, saturated, and class name of paraffins which means Unreactive to other chemicals. • All compounds: Combustion Reaction ROOT ALKANE NAMES • Root names give the number of carbons in the longest continuous chain. Root names are used with various "endings" to indicate branches, type of bonds between carbons, and functional groups. • The following list gives the most basic root the with normal hydrocarbon alkane endings for the number of carbons in the longest continuous chain. Memorize this list. • Example: root = "eth" + alkane ending = "ane" = ethane No. of Root Name Carbons Formula CnH2n+2 Structure 1 methane CH4 CH4 2 ethane C2H6 CH3CH3 3 propane C3H8 CH3CH2CH3 4 butane C4H10 CH3CH2CH2CH3 5 pentane C5H12 CH3CH2CH2CH2CH3 No. of Formula Root Name Carbons CnH2n+2 Structure 6 hexane C6H14 CH3CH2CH2CH2CH2CH3 7 heptane C7H16 CH3CH2CH2CH2CH2CH2CH3 8 octane C8H18 CH3CH2CH2CH2CH2CH2CH2CH3 9 nonane C9H20 CH3CH2CH2CH2CH2CH2CH2CH2CH3 10 decane C10H22 CH3CH2CH2CH2CH2CH2CH2CH2CH2CH3 Cycloalkanes • Cycloalkanes contain a carbon chain that is in the form of a ring. Each cycloalkane has a formula that is 2H less than the corresponding alkane. For example, propane is C3H8 whereas cyclopropane is C3H6. Butane is C4H10 and cyclobutane is C4H8. The names of the cyclic structures use the prefix cyclo in from of the alkane name for the carbon chain. Timberlake LecturePLUS 1999 13 Cycloalkanes Cyclopropane CH2 CH2 CH2 Cyclobutane Timberlake LecturePLUS 1999 CH2 CH2 CH2 CH2 14 More Cycloalkanes Cyclopentane CH2 CH2 CH2 CH2 CH2 Cyclohexane CH2 CH2 CH2 CH2 CH2 CH2 Timberlake LecturePLUS 1999 15 Naming Cycloalkanes with Side Groups Number of side groups One Two Naming Side group name goes in front of the cycloalkane name. Number the ring in the direction that gives the lowest numbers to the side groups and add the number to the name. Timberlake LecturePLUS 1999 16 Cycloalkanes with Side Groups CH3 methylcyclopentane CH3 CH3 1,2-dimethylcyclopentane CH3 CH3 1,2,4-trimethylcyclohexane CH3 Timberlake LecturePLUS 1999 17 ISOMERS • Isomers are compounds which have the same formula but have different forms. Some isomers are known as Structural Isomers because they have a completely different atomic arrangement, while others are called Geometric Isomers because of the spacial arrangement. Isomers of C4H10 Butane 2-Methylpropane Reaction of Alkanes • Alkanes are very unreactive in most cases. The exceptions are Combustion and Halogenation. • Alkanes readily react with oxygen in combustion reactions to form carbon dioxide and water. The shorter chain alkanes are the ones which we normally think of as fuel such as Methane (natural gas), propane for bbqs, butane for lighters and octane for the car. • Halogenation involves the reaction of the alkane with a halogen such as F2, Cl2, Br2, or I2. • The product is an alkyl halide in which a H is replaced by a halogen atom. If the halogen is in excess the reaction contiunes until all H are replaced. • CH4 + F2 → CH3F + HF Fluromethane • CH3F + F2 → CH2F2 + HF Difluoromethane • CH2F2 + F2 → CHF3 + HF Trifluoromethane • CHF3 + F2 → CF4 + HF carbon tetrafluoride