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Diels–Alder Reactions: Predicting Bridged Products and Stereochemistry

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Diels-Alder Reaction - General Features

  • General Features
    09:48

Aromaticity of Annulene

  • [6]annulene vs. [8]annulene
    04:28
  • Determine annulene aromaticity
    01:13
  • Determine annulene aromaticity
    02:10

Counting Pi Electrons

  • Count the pi electrons present
    00:19
  • Count the pi electrons present
    00:12
  • Counting pi electrons
    01:33

Benzene Nomenclature

  • Benzene Nomenclature
    09:04

Four Tests of Aromaticity

  • Four tests
    10:23

Aromaticity of Hydrocarbons

  • Determine the aromaticity
    00:39
  • Determine the aromaticity
    01:06
  • Determine the aromaticity
    02:58

Aromaticity of Heterocycles

  • Determine heterocycle aromaticity
    03:21
  • Heteroatoms
    03:21
  • Determine heterocycle aromaticity
    00:56

SNAr Addition-Elimination Mechanism

  • The Meisenheimer Complex
    06:23
  • Which ipso-substitution is more favored
    03:30
  • General Mechanism
    06:45

Generating Electrophiles – Friedel-Crafts Alkylation

  • Friedel-Crafts Alkylation
    06:30

EAS – Sequence Groups

  • Sequence Groups
    04:42

Generating Electrophiles – Any Carbocation

  • Any Carbocation
    07:21

EAS-o, p-Major Products

  • Ortho, Para major products
    04:42

Benzyne Pathway – General Mechanism

  • Regiospecificity
    03:20
  • General Mechanism
    06:06
  • Activating and deactivating groups
    03:27

EAS – Monosubstituted Benzene

  • Badass Activity Chart
    11:55
  • Activity and Directing Effects
    04:29

Side-Chain Oxidation

  • Benzylic Oxidation
    03:20
  • Which alkylbenzene would NOT yield benzoic acid, treated with KMnO4
    00:49

Blocking Groups - Sulfonic Acid

  • Forcing Ortho substitution
    04:33
  • Multistep Synthesis
    02:15

Generating Electrophiles – EAS Nitration

  • Reduction of Nitro Groups
    03:23
  • EAS Nitration
    06:09

Limitations of Friedel-Crafts Alkyation

  • Limitations
    10:14