ࡱ> G @bjbjَ 1] 4p p p p h p -3P:\v0>2@2@2@2@2@2@2$}4q6d2 d2: :::  >2 &, D >2: :2j.L >2L3_p p  22Chemistry 506: Allied Health Chemistry 2 Chapter 11: Alkenes, Alkynes, and Aromatic Compounds Hydrocarbons with Multiple Bonds Introduction to General, Organic & Biochemistry, 5th Edition by Bettelheim and March: Chapter 11, Pages 353-390 Outline Notes by Dr. Allen D. Hunter, YSU Department of Chemistry, (2000. Outline  TOC \o "1-1" \t "ON Heading 1,1" 11A Section(s) 11.1/2/4 Introduction and Nomenclature of Alkenes  PAGEREF _Toc475716052 \h 3 11B Section(s) 11.3 p-Bonds  PAGEREF _Toc475716053 \h 5 11C Section(s) 11.5 Physical Properties  PAGEREF _Toc475716054 \h 6 11D Section(s) 11.6 Chemical Properties: Addition Reactions  PAGEREF _Toc475716055 \h 7 11E Section(s) 11.7 Addition Polymers  PAGEREF _Toc475716056 \h 9 11F Section(s) 11.8 Alkynes  PAGEREF _Toc475716057 \h 14 11G Section(s) 11.9/10 Aromatic Hydrocarbons  PAGEREF _Toc475716058 \h 18 11H Section(s) 18.2 Amino Acids having Simple Aromatic Side Chains  PAGEREF _Toc475716059 \h 23 11I Section(s) 11.11 Aromatic Reactions  PAGEREF _Toc475716060 \h 24 11J Section(s) 11.12 Fused Ring Aromatics  PAGEREF _Toc475716061 \h 26 11K Section(s) 11.13 Heterocyclics (Not covered in detail)  PAGEREF _Toc475716062 \h 27  11.1/2/4 Introduction and Nomenclature of Alkenes Ethene XE "Ethene"  = (Ethylene XE "Ethylene" ), CH2=CH2 XE "CH2=CH2"  IUPAC Rules XE "IUPAC Rules"  Start numbering from the end that gives the double bond the lowest number. Indicate position of double bond(s) by numbers. Use the ene ending XE "ene ending"  Indicated number of double bonds by prefixes (ene XE "ene" , diene XE "diene" , triene XE "triene" , tetraene XE "tetraene" , etc.) Examples Geometric Isomers XE "Geometric Isomers"  No free rotation XE "free rotation"  (p-bonds XE "p-bonds" ) Experimental observations cis isomers XE "cis isomers"  vs. trans isomers XE "trans isomers"  Examples 11.3 p-Bonds XE "p-Bonds"  Bonding XE "Bonding" : sp2 hybridization XE "sp2 hybridization"  for 3 s-bonds XE "s-bonds"  to the three atoms bonded to each carbon pz XE "pz"  orbital for p-bond XE "p-bond"  Typical C=C bond distance XE "C=C bond distance"  (i.e., 1.34 ( XE "1.34 (" ) shorter than C-C bond distance XE "C-C bond distance"  (i.e., 1.54 ( XE "1.54 (" ) slightly shorter C-H distance XE "C-H distance"  than alkanes XE "alkanes"  11.5 Physical Properties XE "Physical Properties"  Almost identical to Alkanes of same MW Van der Waals forces XE "Van der Waals forces"  Slightly higher Mp XE "Mp"  and Bp XE "Bp"  Smell XE "Smell"  (turpentine like) Density XE "Density"  Solubility XE "Solubility"  11.6 Chemical Properties: Addition Reactions XE "Chemical Properties\: Addition Reactions"  Addition reaction XE "Addition reaction"  (generic) p-bonds weaker than s-bonds XE "p-bonds weaker than s-bonds"  Hydrogenation XE "Hydrogenation" : Addition of H2 XE "H2"  or D2 XE "D2"  (Pt catalyst XE "Pt catalyst" ) Addition of Cl2 XE "Cl2"  or Br2 XE "Br2"  (X2 XE "X2" ) Addition of HX XE "HX"  XE "Addition of HX"  ((HF XE "HF" ) HCl XE "HCl" , HBr XE "HBr"  (HI XE "HI" )) Halide Influences XE "Halide Influences"  Markovnikov Addition XE "Markovnikov Addition"  Addition of Water XE "Addition of Water"  (Hydration XE "Hydration" ) H+ Catalyst XE "H+ Catalyst"  Markovnikov XE "Markovnikov"  11.7 Addition Polymers XE "Addition Polymers"  Definition of Addition Polymers XE "Polymers"  No loss of mass Rapid chain growth XE "chain growth"  p-bond opening XE "p-bond opening"   Generic Synthesis Reaction typical monomers XE "monomers"  are CH2=CH-R XE "CH2=CH-R"  Role of Catalysts XE "Catalysts"  Speed reaction but aren t themselves consumed Highly reactive species Reversibility of Reactions XE "Reversibility of Reactions"  Polymerization XE "Polymerization"  under low temperatures/high pressures i.e., monomer XE "monomer"  (liquids or gasses) -> polymer (solids) Depolymerizations XE "Depolymerizations"  (unraveling) at high temperatures i.e., polymer -> monomer Molecular Weights XE "Molecular Weights"  and Molecular Weight Distributions XE "Molecular Weight Distributions"  High average Molecular Weights Distributions rather than discrete weights Linear Chains XE "Linear Chains"  vs. Branched Chains XE "Branched Chains"  Examples Polyethylene XE "Polyethylene" , PE XE "PE" , Synthesis CH2=CH2 XE "CH2=CH2" , R = H Poly(vinyl chloride) XE "Poly(vinyl chloride)" , PVC XE "PVC" , Synthesis CH2=CH-Cl XE "CH2=CH-Cl" , R = Cl Polypropylene XE "Polypropylene" \t "See" , PP XE "PP" \t "See" , Synthesis CH2=CH-CH3 XE "CH2=CH-CH3" , R = CH3 Polystyrene XE "Polystyrene" , PS XE "PS" , Synthesis CH2=CH-C6H5 XE "CH2=CH-C6H5" , R = C6H5 Poly(methyl methacrylate) XE "Poly(methyl methacrylate)" , PMMA XE "PMMA" , Synthesis CH2=C(CH3)(CO2CH3) XE "CH2=C(CH3)(CO2CH3)"  Teflon XE "Teflon"  Synthesis CF2=CF2 XE "CF2=CF2"  Rubber XE "Rubber"  (Polyisoprene XE "Polyisoprene" ) Synthesis CH2=CH-CH=CH2 XE "CH2=CH-CH=CH2"  11.8 Alkynes XE "Alkynes"  Carbon-Carbon Triple Bonds XE "Carbon-Carbon Triple Bonds"  sp hybridized XE "sp hybridized"  Very Short C(C Bond distance XE "C(C Bond distance"  (i.e., 1.20 ( XE "1.20 ("  ), much shorter than the C=C distance XE "C=C distance"  (i.e., 1.34 ( XE "1.34 (" ) and the C-C distance XE "C-C distance"  (i.e., 1.20 ( XE "1.20 (" ) Bonding XE "Bonding" : 1 s-bond XE "s-bond"  and 2 p-bonds XE "p-bonds"  (px XE "px"  and py XE "py" ) slightly shorter C-H distance XE "C-H distance"  than alkanes or even alkanes Ethyne XE "Ethyne"  = Acetylene XE "Acetylene" , H-C(C-H XE "H-C(C-H"  Physical Properties XE "Physical Properties"  Almost identical to Alkanes/Alkenes of same MW Van der Waals forces XE "Van der Waals forces"  Slightly higher Mp XE "Mp"  and Bp XE "Bp"  Density XE "Density"  Solubility XE "Solubility"  Nomenclature XE "Nomenclature"  yne ending XE "yne ending"  yne > ene XE "ene"  in priority of naming Examples Alkyne Reactions XE "Alkyne Reactions"  Generic Reaction Very like Alkenes XE "Alkenes"  Normally Double Addition XE "Double Addition"  Hydrogenation XE "Hydrogenation" : Addition XE "Addition"  of H2 XE "H2"  or D2 XE "D2"  (Pt catalyst XE "Pt catalyst" ) Addition of X2 XE "X2"  (Cl2 XE "Cl2"  or Br2 XE "Br2" ) Addition of HX XE "HX"  (most commonly HCl XE "HCl"  and HBr XE "HBr" ) Markovnikov Addition XE "Markovnikov Addition"  Addition of H2O XE "H2O"  (H+ catalyst XE "H+ catalyst" ) Markovnikov Addition XE "Markovnikov Addition"  Secondary elimination of water XE "Secondary elimination of water"  from diol XE "diol"  gives carbonyl group XE "carbonyl group"  (aldehyde XE "aldehyde"  or ketone XE "ketone" ) 11.9/10 Aromatic Hydrocarbons XE "Aromatic Hydrocarbons"  Sources Coal Tar XE "Coal Tar"  Coke XE "Coke"  production Direct separation Start of industrial chemistry XE "industrial chemistry"  Petroleum XE "Petroleum"  multiple processing steps Uses Octane XE "Octane"  enhancers in gasoline XE "gasoline"  Plastics XE "Plastics"  Pigments XE "Pigments" /Dyes XE "Dyes"  Pharmaceuticals XE "Pharmaceuticals"  Aromatic XE "Aromatic" : Properties XE "Properties" , Reactivity, C/H Ratios XE "C/H Ratios"  (cf. Alkane/Alkenes/Alkynes) Substitution Reactions XE "Substitution Reactions"  not Addition Reactions XE "Addition Reactions"  (i.e., not like alkenes XE "alkenes" ) Bonding XE "Bonding"  / Resonance Stabilization XE "Resonance Stabilization"  Nomenclature XE "Nomenclature"  IUPAC Names XE "IUPAC Names"  Halobenzenes XE "Halobenzenes"  (X = F, Cl, Br, I) Nitrobenzene XE "Nitrobenzene"  (Z = NO2) Alkylbenzenes XE "Alkylbenzenes"  (phenylalkanes XE "phenylalkanes" ) Common Names XE "Common Names"  (IUPAC) Phenol XE "Phenol"  (Z = OH) Aniline XE "Aniline"  (Z = NH2) Toluene XE "Toluene"  (Z = CH3, methylbenzene XE "methylbenzene" ) Benzoic Acid XE "Benzoic Acid"  (Z = CO2H) Multiply Substituted Arenes XE "Arenes"  Numbering Ring Positions XE "Ring Positions"  Ortho XE "Ortho" , Meta XE "Meta" , Para XE "Para" , Ipso XE "Ipso"  As Side Chains (phenyl groups XE "phenyl groups" ) 18.2 Amino Acids having Simple Aromatic Side Chains XE "Amino Acids having Simple Aromatic Side Chains"  Generic AA = H2N-CHR-CO2H Phenyl Alanine XE "Phenyl Alanine"  (non-polar) R = CH2C6H5 PKU XE "PKU"  11.11 Aromatic Reactions XE "Aromatic Reactions"  Substitution Reactions XE "Substitution Reactions"  Require catalyst XE "catalyst"  "Generic" Z+ XE "Z+"  Electrophiles XE "Electrophiles"  Nitration XE "Nitration"  (Z = NO2, HNO3/H2SO4 XE "HNO3/H2SO4" , TNT XE "TNT" ) Sulfonation XE "Sulfonation"  (Z = SO3H, H2SO4/SO3 XE "H2SO4/SO3" ) Halogenation XE "Halogenation"  (X = Cl or Br, Cl2/Fe XE "Cl2/Fe"  or Br2/Fe XE "Br2/Fe" ) 11.12 Fused Ring Aromatics XE "Fused Ring Aromatics"  Polycyclic Aromatic Hydrocarbons XE "Polycyclic Aromatic Hydrocarbons" , PAH XE "PAH" s Toxicity Naphthalene XE "Naphthalene"  (C10H8 XE "C10H8" ) Anthracene XE "Anthracene"  (C14H10 XE "C14H10" ) Phenanthrene XE "Phenanthrene"  (C14H10) 11.13 Heterocyclics XE "Heterocyclics"  (Not covered in detail) Replace C-H by Heteroatom Groups XE "Heteroatom Groups"  such as: N, O, S, etc. Important in Biomolecules XE "Biomolecules"  Pyridine XE "Pyridine"  (C5H5N XE "C5H5N" ) Problems XE "Problems" : All up to 11.50 Index of Topics and Vocabulary  INDEX \e " " \h "A" \c "2"  1 1.20 ( 13 1.34 ( 4, 13 1.54 ( 4 A Acetylene 13 Addition 15 Addition of HX 7 Addition of Water 7 Addition Polymers 8 Addition reaction 6 Addition Reactions 18 aldehyde 16 alkanes 4 alkenes 18 Alkenes 15 Alkylbenzenes 19 Alkyne Reactions 15 Alkynes 13 Amino Acids having Simple Aromatic Side Chains 22 Aniline 20 Anthracene 25 Arenes 21 Aromatic 17 Aromatic Hydrocarbons 17 Aromatic Reactions 23 B Benzoic Acid 20 Biomolecules 26 Bonding 4, 13, 18 Bp 5, 13 Br2 6, 15 Br2/Fe 24 Branched Chains 9 C C(C Bond distance 13 C/H Ratios 17 C=C bond distance 4 C=C distance 13 C10H8 25 C14H10 25 C5H5N 26 Carbon-Carbon Triple Bonds 13 carbonyl group 16 catalyst 23 Catalysts 8 C-C distance 13 CF2=CF2 12 C-H distance 4, 13 CH2=C(CH3)(CO2CH3) 11 CH2=CH2 2, 10 CH2=CH-C6H5 11 CH2=CH-CH=CH2 12 CH2=CH-CH3 11 CH2=CH-Cl 10 CH2=CH-R 8 chain growth 8 Chemical Properties: Addition Reactions 6 cis isomers 3 Cl2 6, 15 Cl2/Fe 24 Coal Tar 17 Coke 17 Common Names 20 D D2 6, 15 Density 5, 13 Depolymerizations 9 diene 2 diol 16 Double Addition 15 Dyes 17 E Electrophiles 23 ene 2, 14 ene ending 2 Ethene 2 Ethylene 2 Ethyne 13 F free rotation 3 Fused Ring Aromatics 25 G gasoline 17 Geometric Isomers 3 H H+ catalyst 16 H+ Catalyst 7 H2 6, 15 H2O 16 H2SO4/SO3 24 Halide Influences 7 Halobenzenes 19 Halogenation 24 HBr 7, 16 H-C(C-H 13 HCl 7, 16 Heteroatom Groups 26 Heterocyclics 26 HF 7 HI 7 HNO3/H2SO4 23 HX 7, 16 Hydration 7 Hydrogenation 6, 15 I industrial chemistry 17 Ipso 21 IUPAC Names 19 IUPAC Rules 2 K ketone 16 L Linear Chains 9 M Markovnikov 7 Markovnikov Addition 7, 16 Meta 21 methylbenzene 20 Molecular Weight Distributions 9 Molecular Weights 9 monomer 9 monomers 8 Mp 5, 13 N Naphthalene 25 Nitration 23 Nitrobenzene 19 Nomenclature 14, 19 O Octane 17 Ortho 21 P PAH 25 Para 21 PE 10 Petroleum 17 Pharmaceuticals 17 Phenanthrene 25 Phenol 20 Phenyl Alanine 22 phenyl groups 21 phenylalkanes 19 Physical Properties 5, 13 Pigments 17 PKU 22 Plastics 17 PMMA 11 Poly(methyl methacrylate) 11 Poly(vinyl chloride) 10 Polycyclic Aromatic Hydrocarbons 25 Polyethylene 10 Polyisoprene 12 Polymerization 9 Polymers 8 Polypropylene 10 Polystyrene 11 PP 10 Problems 26 Properties 17 PS 11 Pt catalyst 6, 15 PVC 10 px 13 py 13 Pyridine 26 pz 4 R Resonance Stabilization 18 Reversibility of Reactions 9 Ring Positions 21 Rubber 12 S Secondary elimination of water 16 Smell 5 Solubility 5, 13 sp hybridized 13 sp2 hybridization 4 Substitution Reactions 18, 23 Sulfonation 24 T Teflon 12 tetraene 2 TNT 23 Toluene 20 trans isomers 3 triene 2 V Van der Waals forces 5, 13 X X2 6, 15 Y yne ending 14 Z Z+ 23 C-C C-C bond distance 4 p p-bond 4 p-bond opening 8 p-bonds 3, 13 p-Bonds 4 p-bonds weaker than s-bonds 6 s s-bond 13 s-bonds 4  Chemistry 506 Dr. Hunter s Class Chapter 11. PAGE 1 (2000, Dr. Allen D. 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HunterF:\TEACHING\506\ccc Winter 2000, Chem 506\Chemistry 506 Outline Notes for Overhead\Chem 506.Outline Notes.Chapter 11.Win2000.011.docAllen D. HunterF:\TEACHING\506\ccc Winter 2000, Chem 506\Chemistry 506 Outline Notes for Overhead\Chem 506.Outline Notes.Chapter 11.Win2000.011.docAllen D. HunterF:\TEACHING\506\ccc Winter 2000, Chem 506\Chemistry 506 Outline Notes for Overhead\Chem 506.Outline Notes.Chapter 11.Win2000.013.docAllen D. Hunter+H:\public_html\Teaching\Chem506\notes11.doc22l 6 ) [ zx M!t6? Hk uDJ2xD %?E fFH yL !O LVLppI[葂c#n *nllgo KG0w 7>x @|  0 Chapter .0.p0.@ 0)0()0()0()0()P0() hhOJQJo( hhOJQJo( hhOJQJo( hhOJQJo( hhOJQJo( hhOJQJo( hhOJQJo(@ 11 Section(s)  hhOJQJo( hhOJQJo( hhOJQJo( hhOJQJo( hhOJQJo( `o( `o(.`o(..`o(... `o( .... o( ..... o( ...... ppo(.......  ( o(........ `o(`o(.`o(..`o(... `o( .... `o( ..... `o( ...... `o(....... o(........ hhOJQJo( vvo(0o(.0o(..88o(... `o( .... o( ..... o( ...... ppo(.......  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