Chapter 15Organic ChemistryWhich of these are “organic”?CarbonSlide 5Slide 6HydrocarbonsSlide 8Single, double, and triple bondsAlkanes, CnH2n+2Single Bonds - sp3 (tetrahedral)Staggered ConformationsSingle bonds - unrestricted rotationStructures & RotationConformationsConstitutional (structural) isomersSlide 17NamingAlkane examplesSlide 20Physical PropertiesSlide 22Ring strain - cyclopropaneConformations of cyclohexaneSlide 25EnantiomersSlide 27Slide 28Slide 29Alkenes, CnH2n - sp2Geometric IsomersSlide 32Slide 33Slide 34Aromatic - Benzene derivativesSlide 36Slide 37Free-Radical Substitution ReactionsFunctional Groups - Reactive SitesSlide 40Important Reactions 1 - SubstitutionImportant Reactions 2 - AdditionImportant Reactions 3 - EliminationOxidation-reductionFunctional Groups with Single BondsSlide 46Alcohol ReactionsHaloalkane ReactionsSlide 49Slide 50Amine ReactionsFunctional Groups with Double BondsAlkenesSlide 54Aromatic - Substitution ReactionsCharge Distribution & ReactivitySlide 57Oxidation of aldehydes to acidsSubstitutionSlide 60Slide 61Slide 62Substitution of —OH by N in aminesSlide 64Functional Groups with Triple BondsSlide 66Slide 67Types of polymersSlide 69Slide 70Biological PolymersSaccharides/CarbohydratesSlide 73Slide 74Glycosidic linkages (dehydration)DisaccharidesPolysaccharidesSlide 78Slide 79Amino acidsSlide 81Amide Linkage (“peptide bond”)Slide 83Levels of Structure 1Slide 85Slide 86Slide 87Slide 88Slide 89Slide 90Slide 91Slide 92Slide 93Slide 94Slide 95Slide 96Slide 97Slide 98Slide 99Slide 100Chapter 15Organic ChemistryOrganic ChemistryOrganic Chemistry““Organic chemistry …is enough to drive one mad. Organic chemistry …is enough to drive one mad. It gives me the impression of a primeval forest, It gives me the impression of a primeval forest, full of the most remarkable things, a monstrous full of the most remarkable things, a monstrous and boundless thicket, with no way of escape, and boundless thicket, with no way of escape, into which one may well dread to enter.”into which one may well dread to enter.”-Friedrich W-Friedrich WöhleröhlerWhich of these are “organic”?CHCH33CHCH22CHCH22OHOHNaCNNaCNCHCH33COOHCOOHCHCH33(CH(CH22))1616COOHCOOHHCHCCHCHCaCOCaCO33CHCH33CH=CHCH=CH22What is special about carbon?Carbon1. Electron configuration, electonegativity, 1. Electron configuration, electonegativity, and covalent bondingand covalent bonding2. Bond properties, catenation, and 2. Bond properties, catenation, and molecular shapemolecular shape3. Molecular stability3. Molecular stabilityHydrocarbons““Aliphatic”Aliphatic”AlkanesAlkanes Alkenes Alkenes Alkynes Alkynes““Aromatic”Aromatic”CHHH HCHHCHCHHHC CHHSingle, double, and triple bondsC HHHHCHHC HHCH C HCH4C2H4C2H2Alkanes, CnH2n+2““Saturated”Saturated”C9H2022_492Csp3sp3sp3sp3H1sH1sH1sH1sSingle Bonds - sp3 (tetrahedral)109.5°22_494(a) (b)Staggered Conformations22_494(a) (b)22_502HHHHHHCCSingle bonds - unrestricted rotationStructures & Rotation22_493CHHCHHH H(a) (b)EthaneC2H6CH3CH322_493CHHCHHH H(a) (b)StaggeredEclipsedConformationsDifferent spatial arrangements generated by Different spatial arrangements generated by rotation around a single bondrotation around a single bond22_495(a)(b)Constitutional (structural) isomersNaming1.1.Longest C-C chain:Longest C-C chain:root nameroot name2.Suffix:2.Suffix:compound typecompound type3.3.Prefix for rings:Prefix for rings: “cyclo” “cyclo” 4.4.Branches:Branches:root + “yl”root + “yl”alphabeticalalphabeticalnumberednumberedAlkane examples© Mc-Graw-Hill Companies, Inc. All rights reserved.22_496CH3 CH2CH2CH2CH3n-Pentane22_496CH3 CH2CH2CH2CH3n-PentanePhysical PropertiesStraight:Straight:lower melting points, higher boiling pointslower melting points, higher boiling pointsBranched:Branched:higher melting points, lower boiling pointshigher melting points, lower boiling points22_499C CC109.560No "head-on"overlap of atomic orbitals(b)(a)Ring strain - cyclopropane22_500Boat(b)These two Hatoms repeleach otherChair(a)Conformations of cyclohexaneEnantiomers22_501H1ssp2sp2sp2sp2H1s2pCCsp2sp2Alkenes, CnH2n - sp2““Unsaturated”Unsaturated”Geometric IsomersLight energy temporarily excites  bond electrons Bond breaks - allows rotation22_5042p2pH1sHsp2p2pCsp2p2p2pCHH1s2pspAlkynes, CnH2n-2 - sp““Unsaturated”Unsaturated”Aromatic - Benzene derivativesDelocalized (conjugated) Delocalized (conjugated)  electron cloud electron cloudFree-Radical Substitution ReactionsAlkanes:Alkanes:HClCCl ClCHCl4hυ23HBrBrCHCH BrCHCH23hυ233HBrCBrCHCH BrCHCHCHCH CH 33hυ23333Functional Groups - Reactive SitesFunctional Groups - Reactive SitesImportant Reactions 1 - SubstitutionC bonded to same number of atomsC bonded to same number of atoms |R— C — X |:Y |R— C — Y |:XImportant Reactions 2 - AdditionTwo Two  bonds from one bonds from one  bond and one bond and one  bond bondR— C — C — R X—Y X Y | |R— C — C — R | |Important Reactions 3 - EliminationElimination of small, stable molecule + entropyElimination of small, stable molecule + entropyR— C — C — R X—Y X Y | |R— C — C — R | |Oxidation-reductionOxidation:Oxidation:–More bonds to OMore bonds to O–Less bonds to HLess bonds to HReduction:Reduction:–Less bonds to OLess bonds to O–More bonds to HMore bonds to H OR— C H | R— C — OH | OR— C OH | R— C —H |Functional Groups with Single BondsAlcohols & EthersAlcohols & EthersHaloalkanesHaloalkanesAminesAminesR—O —H R—X: X = halogen R— N — | R—O —R Alcohol ReactionsEliminationElimination–Elimination of HElimination of H22O in acidO in acidDehydrationDehydration to C=C to C=C–Elimination of 2 H w/ strong ox.agentElimination of 2 H w/ strong ox.agentOxidation Oxidation to C=Oto C=OSubstitutionSubstitution–Single bonded productsSingle bonded products–““Reactive” C bonded to electronegative atomReactive” C bonded to electronegative atomHaloalkane ReactionsElimination Elimination of HX in very strong baseof HX in very strong baseC=C productC=C productSubstitution Substitution in basein base–Single bonded productsSingle bonded