24.1 Petroleum Refining and the Hydrocarbons24.2 Functional Groups and Organic Synthesis24.3 Pesticides and PharmaceuticalsIRIR Tutor and Infrared SpectroscopyTutor and Infrared SpectroscopyChapter 24From Petroleum toPharmaceuticalsHydrocarbonsHydrocarbonsAromaticAromaticAliphaticAliphaticHydrocarbonsHydrocarbonsAromaticAromaticAliphaticAliphaticAlkanesAlkanesAlkynesAlkynesAlkenesAlkenesHydrocarbonsHydrocarbonsAliphaticAliphaticAlkanesAlkanesAlkanes Alkanes arearehydrocarbons in whichhydrocarbons in whichall of the bonds areall of the bonds aresinglesingle bonds. bonds.CCCCHHHHHHHHHHHHHydrocarbonsHydrocarbonsAliphaticAliphaticAlkenesAlkenesAlkenes areAlkenes arehydrocarbons thathydrocarbons thatcontain a carbon-contain a carbon-carbon carbon doubledouble bond. bond.CCCCHHHHHHHHHydrocarbonsHydrocarbonsAliphaticAliphaticAlkynesAlkynesAlkynes areAlkynes arehydrocarbons thathydrocarbons thatcontain a carbon-contain a carbon-carbon carbon tripletriple bond. bond.HCHCCHCHHydrocarbonsHydrocarbonsAromaticAromaticThe most commonThe most commonaromatic hydrocarbonsaromatic hydrocarbonsare those that containare those that containa benzene ring.a benzene ring. HHHHHHHHHHHHReactive Sites in HydrocarbonsReactive Sites in HydrocarbonsThe Functional GroupThe Functional GroupConceptConceptFunctional GroupFunctional Groupa structural unit in a molecule responsible for itsa structural unit in a molecule responsible for itscharacteristic chemical behavior and itscharacteristic chemical behavior and itsIR spectroscopic characteristicsIR spectroscopic characteristicsAlkanesAlkanesfunctional group is a hydrogen atomfunctional group is a hydrogen atomthe reaction that takes place is the reaction that takes place is termed a substitutiontermed a substitutionone of theone of the hydrogens hydrogens is substitutedis substitutedby some other atom or group, Xby some other atom or group, XRR——HHRR——XXAlkanesAlkanesfunctional group is a hydrogenfunctional group is a hydrogenthe reaction that takes place is substitutionthe reaction that takes place is substitutionone of theone of the hydrogens hydrogens is substitutedis substitutedby some other atom or groupby some other atom or groupRR——HHRR——XX+ + ClCl22CCCCHHHHHHHHHHHH++ HHClClCCCCHHClClHHHHHHHHFunctional Groups in HydrocarbonsFunctional Groups in HydrocarbonsalkanesalkanesRHRHalkenesalkenes RH, double bond RH, double bondalkynesalkynes RH, triple bond RH, triple bondaromaticsaromaticsArHArH, double bond, double bondSome Key Functional GroupsSome Key Functional GroupsFamilies of organic compounds and Families of organic compounds and their functional groupstheir functional groupsAlcoholsAlcoholsROHROHAlkyl halidesAlkyl halidesRX (X = F,RX (X = F, Cl Cl, Br, I), Br, I)AminesAminesprimary amine: RNHprimary amine: RNH22 secondary amine: Rsecondary amine: R22NHNH tertiary amine: Rtertiary amine: R33NNEthersEthersRORRORMany classes of organic compounds Many classes of organic compounds contain a carbonyl groupcontain a carbonyl group OOCCCarbonyl groupCarbonyl group OOCCAcyl Acyl groupgroupRRMany classes of organic compounds Many classes of organic compounds contain a carbonyl groupcontain a carbonyl group OOCCCarbonyl groupCarbonyl group OOCCAldehydeAldehydeRRHHMany classes of organic compounds Many classes of organic compounds contain a carbonyl groupcontain a carbonyl group OOCCCarbonyl groupCarbonyl group OOCCKetoneKetoneRRR'R'Many classes of organic compounds Many classes of organic compounds contain a carbonyl groupcontain a carbonyl group OOCCCarbonyl groupCarbonyl group OOCCCarboxylic acidCarboxylic acidRROHOHMany classes of organic compounds Many classes of organic compounds contain a carbonyl groupcontain a carbonyl group OOCCCarbonyl groupCarbonyl group OOCCEsterEsterRROR'OR'Many classes of organic compounds Many classes of organic compounds contain a carbonyl groupcontain a carbonyl group OOCCCarbonyl groupCarbonyl group OOCCAmideAmideRRNHNH22Introduction toIntroduction to Alkanes Alkanes: : Methane, CHMethane, CH44 Ethane, C Ethane, C22HH66Propane, CPropane, C33HH88CCnnHH22nn+2+2General formula for an General formula for an alkanealkaneThe simplestThe simplest alkanes alkanes Methane (CHMethane (CH44) ) CHCH44 Ethane (CEthane (C22HH66))CHCH33CHCH33Propane (CPropane (C33HH88))CHCH33CHCH22CHCH33bp bp -160°C-160°Cbp bp -89°C-89°Cbp bp -42°C-42°CNo isomers possible for C1, C2, CNo isomers possible for C1, C2, C33 hydrocarbons hydrocarbonsIsomericIsomeric Alkanes Alkanes: : The ButanesThe ButanesCC44HH1010General formula for any butaneGeneral formula for any butanenn-Butane-Butane Isobutane Isobutane CHCH33CHCH22CHCH22CHCH33 (CH(CH33))33CHCHbp bp -0.4°C-0.4°Cbp bp -10.2°C-10.2°CCC44HH1010Higher Higher nn--Alkanes Alkanes Pentane (CPentane (C55HH1212) and Beyond) and BeyondCCnnHH22nn+2+2n > 4n > 4CHCH33CHCH22CHCH22CHCH22CHCH22CHCH33nn-Pentane-Pentanenn-Hexane-HexaneCHCH33CHCH22CHCH22CHCH22CHCH33CHCH33CHCH22CHCH22CHCH22CHCH22CHCH22CHCH33nn--HeptaneHeptaneCCnnHH22nn+2+2n > 4n > 4The CThe C55HH1212 Isomers Isomersnn-Pentane-PentaneCHCH33CHCH22CHCH22CHCH22CHCH33IsopentaneIsopentane(CH(CH33))22CHCHCHCH22CHCH33 NeopentaneNeopentane(CH(CH33))44CC CC55HH1212The number of isomericThe number of isomeric alkanes alkanes increasesincreasesas the number of carbons increase.as the number of carbons increase.There is no simple way to predict how manyThere is no simple way to predict how manyisomers there are for a particular molecularisomers there are for a particular molecularformula.formula.How many isomers?How many isomers?Table 2.3 Table 2.3 Number of Constitutionally IsomericNumber of Constitutionally Isomeric Alkanes AlkanesCHCH4411CC22HH6611CC33HH8811CC44HH101022CC55HH121233CC66HH141455CC77HH161699Table 2.3 Table 2.3 Number of Constitutionally IsomericNumber of Constitutionally Isomeric Alkanes AlkanesCHCH4411 C C88HH18181818CC22HH6611 C C99HH20203535CC33HH8811 C C1010HH22227575CC44HH101022 C C1515HH32324,3474,347CC55HH121233 C C2020HH4242366,319366,319CC66HH141455 C C4040HH828262,491,178,805,83162,491,178,805,831CC77HH161699C6H6 IsomersHow many isomers with thecompositionC6H6 can you draw?C6H6 Isomers: How many isomers with thecompositionC6H6 can you draw?Structure and Bonding in Structure and Bonding in AlkenesAlkenesStructure of EthyleneStructure of Ethylenebond angles: bond angles: H-C-H = 117°H-C-H = 117°H-C-C = 121°H-C-C = 121°bond distances: bond distances: CC——H = 110 pmH = 110 pmC=C =