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Comprehensive Study Guide: Alkyl Halides, Alkenes, and Alkynes (Chapters 6–9)

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Alkyl Halides

  • How to name alkyl halides
    01:52
  • Name the following alkyl halide
    01:58
  • Name the following alkyl halide
    03:53

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

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

The SN1 Mechanism

  • 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

Carbocation Intermediates – Stability

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

Carbocation Intermediate – Rearrangements

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

Leaving Groups

  • Predict the best leaving group
    00:50
  • Predict the best leaving group
    01:12
  • Predict the best leaving group
    00:36

Leaving Groups

  • The 3 important leaving groups to know.
    07:22

Nucleophiles and Basicity

  • Understanding the difference between basicity and nucleophilicity.
    06:21

Solvents

  • The difference between protic vs. aprotic solvents.
    03:57
  • Identification of polarity in solvents
    01:16
  • Identification of polarity in solvents
    00:39

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

Alkenes, Alkynes and Alcohols

  • Name the following alkene
    02:04
  • How to name alkenes and alkynes
    01:55

Index of Hydrogen Deficiency (Structural)

  • Is the following molecule saturated?
    00:30
  • What is the IHD of the following molecule?
    00:45
  • What index of hydrogen deficiency is.
    01:15

Stability of Alkenes

  • Heat of Combustion
    02:55
  • Understanding trends of alkene stability.
    04:28

Cis vs Trans

  • Why we need to use the E/Z naming system
    02:07
  • What does E and Z stand for?
    00:50
  • How to name different types of double bonds or rings
    04:28

Elimination and Zaitsev's Rule

  • Hofmann product
    02:39
  • Defining Zaitsev’s Rule
    01:18
  • Zaitsev product
    07:01

Dehydrohalogenation

  • The dehydrohalogenation mechanism.
    03:02
  • Dehydrohalogenation mechanism and products
    04:35

Acid-Catalyzed Dehydration

  • 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

General Mechanism – Addition Reaction

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

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

Acid-Catalyzed Hydration

  • General properties of acid-catalyzed hydration.
    06:32
  • Acid-catalyzed hydration mechanism
    06:34

Oxymercuration-Reduction

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

Hydroboration-Oxidation

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

Catalytic Hydrogenation and Wilkinson's Catalyst

  • General properties of catalytic hydrogenation.
    05:21

Halogenation

  • Halogenation Mechanism
    03:45
  • General properties of halogenation.
    02:27

Halohydrin Formation

  • Halohydrin Mechanism
    04:48
  • General properties of halohydrin formation.
    01:44

Cyclopropanation

  • Reaction with a simple carbene.
    01:48
  • Reaction with diazomethane and light or heat.
    03:01
  • Reaction with chloroform (CHCl3) and tert-butoxide.
    03:04

Epoxidation

  • Halohydrins to epoxides via intramolecular SN2.
    02:26
  • General properties of epoxidation.
    02:19
  • The mechanism of how peroxy acids make epoxides.
    03:19

Epoxide Ring Opening

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

Syn Vicinal Dihydroxylation

  • General properties of syn vicinal dihydroxylation.
    03:50
  • Predict the product for the following multi-step reaction.
    04:42

Weak Oxidative Cleavage

  • General properties of ozonolysis.
    06:30

Hydrogenation of Alkynes

  • Using Dissolving Metal Reduction or Lindlar’s Catalyst to turn alkynes to alkenes.
    06:08
  • Using Catalytic hydrogenation or Wilkinson’s Catalyst to turn alkynes to alkanes.
    03:46
  • The definition of hydrogenation.
    00:48

Alkyne Hydration

  • Vinyl alcohols yield tautomers.
    03:51
  • Markovnikov addition of alcohols yields ketones.
    03:29