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Hydrocarbons Unsaturated hydrocarbons – Double and triple bonds between carbons – Not every carbon has each of its 4 electrons bonded to 4 different atoms – More chemically reactive than saturated compounds, or alkanes – Unsaturated hydrocarbons include alkenes (double bonds) and alkynes (triple bonds) 1 Parent hydrocarbon prefixes # Carbon atoms Example 1 2 3 4 5 6 7 8 9 10 CH4 methane C2H6 ethane C3H8 propane C4H10 butane C5H12 methethpropbutpenthexheptoctnondec- As attached groups: Functional Group group name pentane -CH3 -C2H5 -C3H7 -C4H9 methyl ethyl propyl butyl C6H14 hexane -C5H11 pentyl C7H16 heptane C8H18 octane C9H20 nonane C10H22 decane 2 1. 2. 3. 4. 5. Naming Organic Compounds Name the parent hydrocarbon: Use the LONGEST STRAIGHT chain of carbon atoms. Add the name of the alkyl groups attached to the chain. If more than one group is attached, use the proper numerical prefix to indicate how many groups are attached. (2=di, 3-tri,etc.) Assign numbers to the carbons in the parent chain. Assign so that attached groups are at the lowest number possible. Insert the numbers in front of the proper group. Separate position numbers from names with hyphens. 3 Example: Naming Organic Compounds 1. Name the parent hydrocarbon. CH3 – CH – CH2 – CH – CH – CH3 hexane CH3 CH3 CH3 2. Add the name of the alkyl groups attached to the chain. 3 methyl groups: trimethylhexane 3. Assign numbers to the carbons in the parent chain. 6 5 4 3 2 1 CH3 – CH – CH2 – CH – CH – CH3 CH3 CH3 CH3 4-5. Insert position numbers and add hyphens. 2,3,5-trimethylhexane 4 Name the following compounds 1. CH3 – CH – CH2 – CH2 – CH3 CH3 2. CH3 – CH – CH2 – CH2 – CH – CH3 | | CH3 CH3 3. CH3 – CH – CH2 – CH2 – CH3 CH2 CH2 5 Unsaturated hydrocarbons • • • • Single bond between carbons: -ane Double bond between carbons: -ene Triple bond between carbons: -yne Examples: H H H C C H H H ethane C2H6 H CnH2n+1 CnH2n CnHn H C C H H C C H H ethene C2H4 ethyne C2H2 6 Other Functional Groups Compound Formula Example Alcohol R-OH hydroxyl group 1-propanol Alkyl Halide -X X = any halide 1,2-dibromopropane Ether R-O-R’ one oxygen bonded to 2 hydrocarbon groups diethyl ether CH3-CH2 –O--CH2--CH3 Aldehyde O || R-C-H Carbonyl group attached to end carbon Ethanal Ketone O || R-C-R’ Carbonyl group attached to a middle carbon 2-propanone O || CH3—C-- CH3 Carboxylic Acid O || R-C-OH Carboxyl group Ester O || R-C-O-R’ Carboxyl group without the H O || CH3—C--H ethanoic acid O || CH3—C—OH methyl ethanoate O || CH3—C—O-- CH3 7 Cyclic Compounds • Cycloalkanes – Saturated carbons joined in a ring – Example is cyclohexane, C6H12 – Add cyclo- to beginning of name if the alkane is known to be arranged in a circle (CnH2n). No position number is needed if only one alkyl group is attached. • Aromatic compounds – Unsaturated: Contains 3 double bonds H-C – Example is benzene, C6H6 C-H H-C CH3CH2- C-H -CH3 1-ethyl-4-methylbenzene H-C C-H benzene 8 Addition Reactions • Water adds to ethene: The double bond is broken and an H attaches to one carbon and the OH attaches to the other carbon. H H HH C C + H-OH H-C-C-H H H HH • Ethene can add to itself, breaking double bonds to attach to one molecule after another. • A monomer is a small unit; when additional monomers are attached repeatedly, a long-chain polymer is formed. 9 Addition Polymers • Polyethylene is a polymer made from the monomer ethene. Zip-lock bags are usually made from lowdensity polyethylene. • Common polymer variations replace one of ethene’s hydrogens with another unit, such as a halogen atom (F or Cl), Cyanide (CN), or benzene (C6H6). – Vinyl chloride – Acrylonitrile – Styrene polyvinyl chloride polyacrylnitrile polystyrene • Atoms that compose the monomers determine the properties of the polymer. 10