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Study Guide: Chapters 5–9 – Alkenes, Alkynes, Substitution & Elimination, and Multistep Synthesis

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Carbocation Intermediates – Stability

  • Determining Carbocation Stability
    05:58
  • Predicting the most stable carbocation
    01:21

Markovnikov's Rule

  • Provide the mechanism
    01:26
  • How to add to asymmetrical double bonds.
    03:38

Radical Hydrohalogenation

  • Provide the complete mechanism for the following radical hydrohalogenation.
    02:53
  • How Radical Hydrohalogenation is different from typical Hydrohalogenation.
    07:13
  • Overview of Hydrohalogention.
    01:18

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

Overview of Chemical Reactions

  • Recognizing Substitution Reactions.
    01:34
  • Recognizing Acid-Base Reactions.
    02:43
  • Recognizing Elimination Reactions.
    00:40

General Mechanism – Addition Reaction

  • Provide the mechanism
    01:15
  • Features of Addition Mechanisms.
    05:39

Hydroboration-Oxidation

  • General properties of hydroboration-oxidation.
    06:38
  • Acid-catalyzed hydroboration-oxidation mechanism
    06:14

Hydrohalogenation

  • General properties of hydrohalogenation.
    04:07
  • Provide the mechanism
    02:24

Oxymercuration-Reduction

  • Acid-catalyzed oxymercuration-reduction mechanism
    09:01
  • General properties of oxymercuration-reduction.
    05:

Markovnikov's Rule

  • Provide the mechanism
    01:26
  • How to add to asymmetrical double bonds.
    03:38

Carbocation Intermediate – Rearrangements

  • Alkyl Shift
    03:43
  • Understanding why carbocations shift.
    00:47
  • Hydride Shift
    03:34

Radical Initiators

  • What are Radical Initiators?
    03:49
  • Heterolytic vs. Homolytic Bond Cleavage .
    04:39

Radical Chain Reaction

  • The one reaction that alkanes will actually undergo.
    02:05
  • Explaining the following problem.
    00:34
  • Show the entire chain reaction mechanism.
    04:08

Allylic Halogenation

  • Predict the product(s) of the following reaction.
    04:28
  • Mechanism of Allylic Bromination.
    00:54
  • The products of Allylic Chlorination.
    00:48

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

Radical Selectivity

  • Predict the Product.
    00:48
  • Predict the Product.
    01:02
  • Using the Hammond Postulate to describe radical chlorination.
    03:03