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Comprehensive Study Guide: Alcohols, Ethers, and Epoxides (Chapters 10 & 11) and Key Organic Chemistry Concepts

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Functional Groups

  • Assigning Degrees to Alkyl Halides
    01:30
  • Why we need functional groups.
    01:49
  • The difference between aldehydes and ketones.
    03:08

Formal Charges

  • Calculate the formal charges of ALL atoms.
    02:21
  • Calculating formal and net charge.
    01:34

Resonance Structures

  • How to draw a resonance hybrid.
    03:24
  • The rules you need for resonance:
    03:34
  • How to determine which structure is most stable.
    01:32

Hybridization

  • How carbon creates 4 partially-filled orbitals.
    02:53
  • Bond sites, hybridization, and intermediate orbitals
    04:58
  • Introduction to the reactive intermediates.
    02:47

Newman Projections – Conformational Energy

  • 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

Chair Flip

  • The 3 important factors when drawing chairs
    05:12

Chirality

  • Drawing Mirror Images and Determining Chirality
    03:24
  • What is chirality?
    05:10
  • Drawing Mirror Images and Determining Chirality
    03:44

Cahn-Ingold-Prelog Nomenclature

  • R and S Naming- Step 4
    03:07
  • Why stereoisomers need their own naming system.
    01:48
  • Determining Priorities
    01:19

Types of Stereoisomers

  • Determine total number of stereoisomers
    00:49
  • How to predict the total number of stereoisomers.
    01:03
  • Draw stereoisomers and determine relationship
    07:41

Molecular Geometry

  • Predict the hybridization and molecular geometry
    01:54
  • Molecular Geometry Explained.
    07:44

pKa Values

  • Identifying pKa values
    07:45
  • The 12 pKa values you want to memorize (because they are important!).
    09:36

Acid and Base Definitions

  • Lewis vs. Bronsted-Lowry Definition
    07:46
  • The Bronsted-Lowry definition of acids and bases.
    00:54
  • Equilibrium constant and conjugates.
    02:11

Acid Base Equilibrium

  • The 3 steps for determining the direction of acid and base equilibrium.
    05:11
  • Determining Acid/Base Equilibrium
    04:00
  • Determining Acid/Base Equilibrium
    02:34

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

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

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

Hydrohalogenation

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

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

Intro to Redox

  • Distinguishing between Oxidation and Reduction
    00:54
  • Distinguishing between Oxidation and Reduction
    01:18
  • Distinguishing between Oxidation and Reduction
    00:54

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

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

Solvents

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

Leaving Groups

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

Nucleophiles and Basicity

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

SN1 SN2 E1 E2 Chart (Big Daddy Flowchart)

  • How to predict SN2 and E2 mechanisms.
    09:52
  • How to predict SN1 and E1 mechanisms.
    06:30
  • Overview of the flowchart.
    02:27

Elimination and Zaitsev's Rule

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

Alcohol Nomenclature

  • Provide the correct common and IUPAC name.
    01:49
  • How to name polyols.
    01:47
  • Provide the correct common and IUPAC name.
    00:59

Synthesis of Alcohols Overview

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

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

Oxidization

  • Reagents
    01:52
  • Strong oxidizing agents
    05:53
  • Strong oxidizing agents
    03:40

Alkyl Halides

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

Williamson Ether Synthesis

  • The Mechanism of Williamson Ether Synthesis.
    03:50

Cleavage of Ethers

  • How to predict the products of Ether Cleavage.
    04:22
  • Predict the product of the following reaction.
    03:44

Alcohol Protecting Groups

  • General features of Alcohol Protecting Groups.
    03:01

Silyl Ether Protecting Groups

  • Mechanism of Silyl Ether Protecting Groups.
    07:16
  • Predict the product of the following reaction.
    03:37

Epoxide Nomenclature

  • How to name cyclic ethers using the cycloalkane convention.
    03:23
  • How to name epoxides using the epoxy convention.
    01:20
  • Defining what an epoxide (oxirane) is.
    01:09

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