Carbanion Stability (time in minutes)

  26 Carbanion Hydridization and Stability (0:56)
  27 Carbanion Hydridization and Stability, narrated (1:52)

  Carbonyl Chemistry (time in minutes)

  97 Hydration, Basic Conditions, narrated (1:59)
  98 Hydration, Acid Conditions, narrated (3:19)
  99 Cyanohydrin Formation, HCN Addition (9:21)
 100 Keto-Enol Tautormerization, Base Conditions (0:24)
 101Keto-Enol Tautormerization, Acid Conditions (0:34)
 102 Alpha Halogenation, Acid Conditions (0:50)
 103 Carbonyl and gem-diol Equilibrium, narrated (6:04)

 104 Acetal and Hemiacetal Formation, narrated (6:07)

  Radical Stability (time in minutes)

  24 Radical Substitution, Hyperconjugation (0:50)
  25 Radical Substitution, Hyperconjugation, narrated (1:35)

  Molecules (time in minutes)

 105 Methane (0:20)*
 106 Ethane (0:20)
 107 Ethanes in a Box (0:25)
 108 Propane (0:20)*
 109 Ethene (0:20)
 110 Ethene, with p-orbitals (0:20)*
 111 Ethyne (0:20)
 112 Ethyne, with p-orbitals (0:20)*
 113 Allene (0:20)
 114 Allene, with p-orbitals (0:20)

 115 1,3-Butadiene (0:20)

 116 1,3-Butadiene, with p-orbitals (0:24)
 117 Formaldehyde (0:24)
 118 Formaldehyde, with p-orbitals (0:24)
 119 N,N-Dimethylformamide (0:21)

 120 N,N-Dimethylformamide Rotation and Orbitals (1:29)
 121 Cyclopropane (0:20)

 122 Ethylene Oxide (0:20)

 123 Cyclobutane (0:20)
 124 Cyclobutadiene (0:24)
 125 Cyclopentane (0:20)*
 126 Cyclopentadienyl Anion (0:24)
 127 Benzene (0:20)
 128 Benzene, with p-orbital array (0:21)
 129 Cycloheptatriene (0:22)
 130 Cycloheptatrienyl Cation (0:24)
 131 Cyclooctatetraene (0:30)
 132 tert-Butyl Cation (0:20)
 133 tert-Butyl Radical (0:20)*
 134 Allyl Cation (0:24)
 135 Allyl Radical (0.24)*
 136 Benzyl Cation (0:21)
 137 Cyclopentadienyl Anion (0:24)
 138 Cycloheptatrienyl Cation (0:24)

34 Alkene Stability Part 2

  Reactions of Epoxides (time in minutes)

  67 Nucleophilic Ring Opening (0:31)*
  68  Acid-Catalyzed Ring Opening (0:29)

  Valence Bond Theory (time in minutes)
   1 sp3 hybridization (1:03)
   2 sp3 hybridization, narrated (1:05)*
   3 sp2 hybridization (1:09)
   4 sp2 hybridization, narrated (1:09)*
   5 sp hybridization (1:14)
   6 sp hybridization, narrated (1:14)*

  Benzene Stability and Aromaticity (time in minutes)

  87 Benzene and Stability, narrated (4:03)

  88 Benzene and Huckel, narrated (7:43)

56 SN2 Rxn with R-X, Electron Pushing

  Diene Chemistry (time in minutes)

  76 Diels-Alder 1 Fundamentals, narrated (4:04)

  77 Diels-Alder 2 Diene and Dienophile Substituents, narrated (3:46)

  78 Diels-Alder 3 Stereochemistry, Dienophiles, Endo Rule,

       narrated (3:34)

  79 Diels-Alder I (0:46)*
  80 Diels-Alder II Endo Rule (0:24)

   Aromaticity and Stability (time in minutes)

  13 Benzene and Stability, narrated (4:03)
  14 Benzene and Huckel, narrated (7:43)

  Formation of Epoxides (time in minutes)

  65 Epoxides from Halohydrins (0:27)*
  66 Epoxidation of Alkenes (0:27)

  Alkene Stability (time in minutes)

  33 Alkene Stability Part 1, narrated (5:37)
  34 Alkene Stability Part 2, narrated (5:30)

35 Dienes and Stability, narrated

  Diene Stability (time in minutes)

  35 Dienes and Stability, narrated (6:32)
  36 Butadiene Rotation (1:03)
  37 Butadiene Rotation, narrated (2:59)

42 E1 Rxn with RX

  Elimination Rxns with Alcohols (time in minutes)

  38 E1 Rxn with R-OH (0:48)
  39 E1 Rxn with R-OH, Rxn Coordinate (0:48)
  40 E2 Rxn with R-OH (0:40)

29 Enantiomers, narrated

  Substitution Rxns with Alcohols (time in minutes)

  49 SN1 Rxn with R-OH (0:35)
  50 SN1 Rxn with R-OH, Rxn Coordinate (0:31)
  51 SN2 Rxn with R-OH (0:50)
  52 SN2 Rxn with R-OH, Rxn Coordinate (0:45)

  Free Radical Halogenation (time in minutes)

  69 Radical Chlorination of Methane, narrated (4:49)

  Benzene Reactions (time in minutes)

  89 Benzene Bromination (0:37)*
  90 Benzene Bromination, Rxn Coordinate (0:33)*
  91 Benzene Sulfonation (0:44)
  92 Benzene Sulfonation, Rxn Coordinate (0:35)
  93 Benzene Nitration (0:44)
  94 Benzene Nitration, Rxn Coordinate (0:44)
  95 Friedel-Crafts Alkylation (0:40)
  96 Friedel-Crafts Acylation (0:36)

  Stereochemistry (time in minutes)

  28 Enantiomers (1:05)
 29 Enantiomers, narrated (2:27)*
  30 Diastereomers, narrated (3:33)
  31 Meso Molecules, narrated (4:33)

  32 cis trans Alkenes are Diasteromers, narrated

33 Alkene Stability Part 1

  Reactions of Alkynes: Alkene Formation (time in minutes)

  85 Trans Alkenes from Alkynes (0:40)
  86 Trans Alkenes from Alkynes, narrated (1:49)*

23 Carbocation  Substitution, Hyperconjugation,

   Induction, narrated

  Cyclohexane Conformational Analysis (time in minutes)

  15 Drawing Cyclohexane's Chair Conformation (4:35)

  16  Cyclohexane Conformations (0:21)
  17 Cyclohexane Conformations, narrated (1:21)
  18  Cyclohexane Energy Diagram (0:40)
  19 Cyclohexane Energy Diagram, narrated (1:13)
  20 Methylcyclohexane (0:44)

  21 Methylcyclohexane, narrated (3:14)

  Alkane Conformational Analysis (time in minutes)
    7 Chemical Representations (1:28)*
    8 Chemical Representations, narrated (1:24)
    9 Ethane Rotation (0:44)*
  10 Ethane Rotation, narrated (1:17)
  11 Butane Rotation (0:21)
  12 Butane Rotation, narrated (1:23)*

  Alkene Reactions (time in minutes)

  70 Hydrogenation (0:48)*
  71 Bromination (0:35)*
  72 Br-OH Addition, Halohydrin Formation (0:46)
  73  H-X Addition (0:29)
  74  Epoxidation (0:27)
  75 Hydroboration-Oxidation, narrated (7:44)

  Elimination Rxns with Alkyl Halides (time in minutes)

  41 E1 Reaction with R-X, electron pushing, narrated (3:59)
  42 E1 Rxn with R-X (1:09)
  43 E1 Rxn with R-X, Rxn Coordinate (0:46)
  44 E2 Rxn with R-X, electron pushing, narrated (5:05)*
  45 E2 Rxn with R-X (0:41)*
  46 E2 Rxn with R-X, Rxn Coordinate (0:48)*
  47 E2 Rxn with R-X, Regiochemistry 1, narrated (3:59)
  48 E2 Rxn with R-X, Regiochemistry 2, narrated (4:00)

  Alkynyl Chemistry (time in minutes)

  81 Alkyne Alkylation (0:24)*
  82 Hydridization and Stability (0:56)
  83 Hydridization and Stability, narrated (1:52)
  84 Cis Alkenes from Alkynes (0:44)

  Carbocation Stability (time in minutes)

  22 Carbocation  Substitution, Hyperconjugation, Induction (1:00)
  23 Carbocation  Substitution, Hyperconjugation, Induction, 

       narrated (1:57)*

  Substitution Rxns with Alkyl Halides (time in minutes)

  53 SN1 Rxn with R-X, narrated (3:33)
  54 SN1 Rxn with R-X (0:31)
  55 SN1 Rxn with R-X, Rxn Coordinate (0:34)
  56 SN2 Rxn with R-X, Electron Pushing (2:53)*
  57 SN2 Rxn with R-X, Hydroxide Nucleophile (0:21)

  58 SN2 Rxn with R-X, Hydroxide Nucleophile, Rxn Coord. (0:21)

  59 SN2 Rxn with R-X, Methylsulfide Nucleophile (0:35)
  60 SN2 Rxn with R-X, Methylsulfide Nucleophile, Rxn Coord. (0:35)

  61 SN2 Rxn with R-X, Hydroxide Nucleophile, legacy ed. (0:26)*
  62 SN2 Rxn with R-X, Rxn Coordinate, legacy ed. (0:22)*
  63 SN2 Rxn with R-X, Stereochemistry (0:27)*
  64 SN2 Rxn with R-X, Molecular Orbitals (0:25)