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Nucleophilic Substitution and Elimination Reactions: Mechanisms, Energy Profiles, and Stereochemistry

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Introduction to Substitution

  • Predict the product
    05:55
  • Nucleophiles and Electrophiles can react in Bronsted-Lowry Reactions.
    05:01
  • Nucleophiles and Electrophiles can react in Substitution Reactions.
    01:47

SN1 Reaction

  • Drawing the SN1 Mechanism
    10:49
  • Why highly substituted leaving groups favor SN1.
    01:13
  • Understanding the properties of SN1.
    08:16

The SN2 Mechanism

  • Ranking reactivity toward SN2
    04:03
  • Drawing the SN2 Mechanism
    08:33
  • Understanding the properties of SN2.
    11:57

Reaction Mechanism

  • How to tell if charged molecules will react as nucleophiles or electrophiles.
    02:39
  • Nucleophile or Electrophile
    01:49
  • How to tell if uncharged molecules will react as nucleophiles or electrophiles.
    02:48

Energy Diagram

  • Favorability and rate of Free Energy Diagrams
    01:14
  • Favorability and rate of Free Energy Diagrams
    00:34
  • Favorability and rate of Free Energy Diagrams
    02:18

The E1 Mechanism

  • Understanding the properties of E1.
    03:32
  • Drawing the E1 Mechanism.
    08:09

E2 Mechanism

  • Understanding the properties of E2.
    04:42
  • Drawing the E2 Mechanism.
    09:36
  • Rank reactivity toward E2
    02:03

Barrier To Rotation

  • 4 Values You Should Memorize
    02:54
  • Determining energy cost of eclipsed interaction
    03:00

Newman Projections

  • How to draw a Newman Projection Energy Diagram.
    07:27
  • How sigma bond rotation is visualized
    03:11
  • The energy states of 3 different Newman Projections.
    03:51

Drawing Newman Projections

  • Step 6 to Drawing Newman Projections
    01:31
  • Step 5 to Drawing Newman Projections
    01:51
  • Step 3 to Drawing Newman Projections
    00:28

Alcohol Synthesis

  • Forming alcohols through SN2 reactions.
    01:44
  • Forming alcohols through Acid-Catalyzed Hydration.
    02:02
  • Forming alcohols through Hydroboration-Oxidation.
    01:37

Dehydration Reaction

  • Dehydration of 1° alcohols:The E2 Mechanism
    05:20
  • An extra note of caution with 1° alcohols.
    01:06
  • General features of acid-catalyzed dehydration.
    06:01

POCl3 Dehydration

  • Mechanism of Dehydration with POCl3
    04:52
  • General Reaction of Dehydration with POCl3
    01:23

Epoxide Reactions

  • Base-Catalyzed Epoxide Ring-Opening
    04:44
  • Acid-Catalyzed Epoxide Ring-Opening
    04:34