Organic ChemistrySlide 2Slide 3Slide 4Slide 5Slide 6Slide 7Slide 8Slide 9Slide 10Slide 11Slide 12Slide 13Slide 14Slide 15Slide 16Slide 17Slide 18Slide 19Slide 20Slide 21Slide 22Slide 23Slide 24Slide 25Slide 26Slide 27Slide 28Slide 29Slide 30Slide 31Slide 32Slide 33Slide 34Slide 35Organic ChemistryChapter 24Copyright © The McGraw-Hill Companies, Inc. Permission required for reproduction or display.24.1Common Elements in Organic Compounds24.1Classification of Hydrocarbons24.2AlkanesAlkanes have the general formula CnH2n+2 where n = 1,2,3,…• only single covalent bonds• saturated hydrocarbons because they contain the maximum number of hydrogen atoms that can bond with the number of carbon atoms in the moleculeCH4C2H6C3H8methane ethane propane24.2Structural isomers are molecules that have the same molecular formula but different structuresHow many structural isomers does pentane, C5H12, have?C C C CCH H H H HHHHHHHHC C CCH CH3H HHHHHHHC CCH CH3HHHHHCH3n-pentane2-methylbutane2,2-dimethylpropane24.224.2Alkane Nomenclature1. The parent name of the hydrocarbon is that given to the longest continuous chain of carbon atoms in the molecule.CH3CH2CH2CH CH2CH2CH3CH31 2 3 4 5 6 74-methylheptane2. An alkane less one hydrogen atom is an alkyl group.CH4CH3methanemethyl24.2Alkane Nomenclature24.2Alkane Nomenclature3. When one or more hydrogen atoms are replaced by other groups, the name of the compound must indicate the locations of carbon atoms where replacements are made. Number in the direction that gives the smaller numbers for the locations of the branches.CH3CH CH2CH2CH3CH31 2 3 4 52-methylpentaneCH3CH2CH2CH CH3CH31 2 3 4 54-methylpentane24.2Alkane Nomenclature4. Use prefixes di-, tri-, tetra-, when there is more than one alkyl branch of the same kind.CH3CH CH CH2CH2CH3CH31 2 3 4 5 6CH32,3-dimethylhexaneCH3CH C CH2CH2CH3CH31 234 5 6CH33,3-dimethylhexane24.2Alkane Nomenclature5. Use previous rules for other types of substituents.CH3CH CH CH3Br1 2 3 4NO22-bromo-3-nitrobutaneCH2CH2CH CH3Br1 2 3 4NO21-bromo-3-nitrobutaneWhat is the IUPAC name of the following compound?24.21 2 3 4 5 6 78CH3CH CH2CH CH2CH2CH3C2H5CH2CH32-methyl-4-ethyloctaneWhat is the structure of 2-propyl-4-methylhexane?1 2 3 4 5 6CH3CH CH2CH CH2CH3CH3C2H524.2Alkane ReactionsCH4 (g) + 2O2 (g) CO2 (g) + 2H2O (l) H0 = -890.4 kJCombustionHalogenationCH4 (g) + Cl2 (g) CH3Cl (g) + HCl (g)lightCl2 + energy Cl• + Cl•Cl• +C HHHHC HHH• + HClCHHH•+ Cl Cl C ClHHH+ Cl•24.2achiral chiral24.2CycloalkanesAlkanes whose carbon atoms are joined in rings are called cycloalkanes. They have the general formula CnH2n where n = 3,4,…Cycloalkanes24.224.2AlkenesAlkenes have the general formula CnH2n where n = 2,3,…• contain at least one carbon-carbon double bond• also called olefinsCH2CH CH2CH31-buteneCH3CH CH CH32-buteneC CCl ClH HC CCl HH Clcis-dichloroethylene trans-dichloroethyleneCis-Trans Isomerization in the Vision Process24.224.2Alkene ReactionsCrackingAddition ReactionsCH2 CH2 (g) + HBr (g) CH3 CH2Br (g)CH2 CH2 (g) + Br2 (g) CH2Br CH2Br (g)C2H6 (g) CH2 CH2 (g) + H2 (g)Ptcatalyst24.2AlkynesAlkynes have the general formula CnH2n-2 where n = 2,3,4,…• contain at least one carbon-carbon triple bond1-butyne 2-butyneCHC CH2CH3CH3C C CH3Production of acetyleneCaC2 (s) + 2H2O (l) C2H2 (g) + Ca(OH)2 (aq)24.2Alkyne ReactionsAddition ReactionsHydrogenationCH CH (g) + H2 (g) CH2 CH2 (g)CH CH (g) + HBr (g) CH2 CHBr (g)CH CH (g) + Br2 (g) CHBr CHBr (g)CH CH (g) + 2Br2 (g) CHBr2 CHBr2 (g)Chemistry In Action: Ice That Burns24.3Aromatic HydrocarbonsCCCCCCHHHHHHCCCCCCHHHHHH24.3Aromatic Compound NomenclatureCH2CH3ethylbenzeneClchlorobenzeneNH2aminobenzeneNO2nitrobenzene123456BrBr1,2-dibromobenzeneBrBr1,3-dibromobenzene24.3Aromatic Compound ReactionsHHHHHHBrHHHHH+ HBr+ Br2FeBr3catalystHHHHHHCH2CH3HHHHH+ HCl+ CH3CH2ClAlCl3catalystSubstitution reaction24.3Polycyclic Aromatic Hydrocarbons24.4Functional Group ChemistryAlcohols contain the hydroxyl functional group and have the general formula R-OH.C6H12O6 (aq) 2CH3CH2OH (aq) + 2CO2 (g)enzymeCH2 CH2 (g) + H2O (g) CH3CH2OH (g)H2SO4Biological production of ethanolCommercial production of ethanolMetabolic oxidation of ethanolCH3CH2OH CH3CHO + H2alcohol dehydrogenase24.424.4Functional Group ChemistryEthers have the general formula R-O-R’.CH3OH + HOCH3 CH3OCH3 + H2OH2SO4catalystCondensation Reaction24.4Functional Group ChemistryAldehydes and ketones contain the carbonyl ( ) functional group.OCR C HO• aldehydes have the general formulaR C R’O• ketones have the general formula H C HOH COCH3COCH3H3Cformaldehyde acetaldehyde acetone24.4Functional Group ChemistryCarboxylic acids contain the carboxyl ( -COOH ) functional group.24.4Functional Group ChemistryEsters have the general formula R’COOR, where R is a hydrocarbon group.CH3COOH + HOCH2CH3 CH3 C O CH2CH3 + H2OOethyl acetate24.4Functional Group ChemistryAmines are organic bases with the general formula R3N.CH3NH2 + H2O RNH3+ + OH-CH3CH2NH2 + HCl CH3CH2NH3+Cl-24.4Chemistry In Action: The Petroleum IndustryCrude