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Comprehensive Study Guide: Advanced Organic Chemistry Concepts and Mechanisms

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1H Nuclear Magnetic Resonance - General Features

  • General NMR Features
    10:06

1H NMR - Total Number of Signals

  • General Assumption for 1H NMR Signals
    04:35
  • Identifying Proton Signals
    02:02
  • Identifying Proton Signals
    01:55

1H NMR - Spin-Splitting without J-Values

  • Splitting without J-values
    12:21
  • Proton Splitting
    03:

1H NMR - Integration

  • 1H NMR Integration
    06:46
  • Draw Complete NMR Spectrum
    04:29

13C NMR - General Features

  • 13C NMR General Features
    04:00
  • 1H and 13C Joint Problem
    01:10
  • Identifying 13C Signals
    02:12

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

Functional Groups

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

Introduction to Conjugation

  • Conjugated states
    03:27
  • Definition of Conjugation
    05:29
  • Review of Common Resonance Structures
    04:50

Stability of Conjugated Intermediates

  • Stability of Conjugated Intermediates
    04:31

Frontier Molecular Orbital Theory - Finding HOMO/LUMO

  • HOMO vs. LUMO
    02:35

Allylic Halogenation

  • Specific Reactions - Allylic Chlorination
    03:
  • Allylic Halogentation - General Mechanism
    07:50
  • Specific Reactions - Allylic Bromination
    03:20

Diels-Alder Reaction - General Features

  • General Features
    09:48

Aromaticity - Introduction

  • Intro to Aromaticity
    08:19

Four Tests of Aromaticity

  • Four tests
    10:23

Electrophilic Aromatic Substitution – General Mechanism

  • EAS General Mechanism
    06:52
  • EAS Review
    03:07

Electrophilic Aromatic Substitution – Reactions

  • EAS Reactions Overview
    11:50

Generating Electrophiles – EAS Halogenation

  • EAS Halogenation
    06:26

Generating Electrophiles – EAS Nitration

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

Generating Electrophiles – Friedel-Crafts Alkylation

  • Friedel-Crafts Alkylation
    06:30

Generating Electrophiles – Friedel-Crafts Acylation

  • Friedel-Crafts Acylation
    05:20

EAS-o, p-Major Products

  • Ortho, Para major products
    04:42

SNAr Addition-Elimination Mechanism

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

Aldehyde Nomenclature

  • Name the aldehyde
    01:34
  • Name the aldehyde
    03:17
  • Nomenclature
    03:11

Ketone Nomenclature

  • Name the ketone
    01:58
  • Nomenclature
    03:05
  • Name the ketone
    02:27

Intro to Redox

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

Oxidation

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

Weak Oxidative Cleavage

  • General properties of ozonolysis.
    06:30

Alkyne Hydration

  • Alkyne Hydration
    09:11

Nucleophilic Addition

  • Nucleophilic Addition
    08:27

Reactions of Organometallics

  • Reactions of Organometallics
    13:40

Hydrates

  • Show the mechanism, predict the equilibrium
    01:57
  • Mechanism
    04:10

Hemiacetals

  • Acid-Catalzed Mechanism
    04:08
  • Base-Catalyzed Mechanism
    01:59
  • General Features
    03:34

Acetals

  • General Mechanism
    06:41

Acetals as Protecting Groups

  • Protecting Groups
    02:44
  • Acetal Protecting Group
    04:29

Imines and Enamines

  • Imine Mechanism
    06:23
  • Enamine Mechanism
    06:25
  • General Reactions
    02:27

Cyanohydrins

  • Nitrile Reduction
    02:36
  • Nitrile Hydrolysis
    02:22
  • Addition of Cyanide
    03:53

Wittig Reaction

  • Box-Out Method and Full-Mechanism
    15:39

COOH Derivatives and Nucleophilic Acyl Substitution

  • Intro to Nucleophilic Acyl Substituion
    04:06
  • Intro to Carboxylic Acid Derivatives
    03:50

Carboxylic Acid Nomenclature

  • Give the IUPAC name
    02:03
  • Carboxylic Acids Nomenclature
    04:20

Ester Nomenclature

  • Draw the molecule
    01:28
  • Name the structure
    01:10
  • Ester Nomenclature
    02:39

Nitrile Nomenclature

  • Name the structure
    00:50
  • Nitrile Nomenclature
    01:01
  • Draw the molecule
    00:28

Acid Chloride Nomenclature

  • Acid Chloride Nomenclature
    03:13
  • Provide the IUPAC name for the molecule
    01:44
  • Draw the Acid-Chloride
    00:37

Anhydride Nomenclature

  • Draw the molecule
    00:40
  • Anhydride Nomenclature
    03:35
  • Provide the IUPAC name for the molecule
    02:47

Amide Nomenclature

  • Amide Nomenclature
    01:33
  • Name the molecule
    02:46
  • Draw the amide
    01:28

Nucleophilic Acyl Substitution – The Three Rules

  • NAS - The Three Rules
    09:32

Specific Carboxylic Acid Conversions

  • Synthesis of Acid Chlorides
    01:36
  • Hydrolysis of Nitriles
    01:11
  • Synthesis of Amides
    02:32

Fischer Esterification – Mechanism

  • General Mechanism
    04:08
  • General Reaction
    01:08

Acid-Catalyzed Ester Hydrolysis – Mechanism

  • General Mechanism
    02:38
  • General Reaction
    01:31

Base-Catalyzed Ester Hydrolysis – Mechanism

  • Mechanism
    03:27

Base-Catalyzed Transesterificaation – Mechanism

  • General Mechanism
    02:27
  • General Reaction
    02:49

Lactones, Lactams and Cyclization Reactions

  • Lactones and Lactams
    05:19
  • Cyclic Anhydrides and Imides
    03:35
  • Cyclization Reaction
    01:33

Carbonation of Grignard Reagents

  • Carbonation of Grignard Reagents
    02:12

Decarboxylation

  • Predict the correct structure
    02:32
  • General Mechanism
    04:32

Alpha Carbons and Tautomerization

  • Tautomerization Mechanisms
    05:11
  • Unusual Acidity of the Alpha Carbon
    01:51

Tautomers of Dicarbonyl Compounds

  • Tautomers of Dicarbonyls
    04:48
  • Acidic Ketones
    02:07

Enolates

  • General Reactions
    02:28
  • Formation of Enolates
    02:26

Acid-Catalyzed Alpha-Halogenation

  • Acid Catalyzed
    03:09

Base-Catalyzed Alpha-Halogenation

  • Base Catalyzed
    01:57

Haloform Reaction

  • Haloform Reaction
    03:50

Hell-Volhard-Zelinski Reaction

    Overview of α-Carbon Alkylations and Acylations

    • Overview
      06:12

    Enolate Alkylation and Acylation

    • Alkylation of Esters
      03:05
    • General Reaction
      01:11
    • Directed Reactions
      04:35

    Enamine Alkylation and Acylation

    • General Reaction
      03:36
    • Predict the Products
      02:50
    • Predict the Products
      03:13

    Beta-Dicarbonyl Synthesis Pathway

    • General Mechanism
      07:29

    Acetoacetic Ester Synthesis

    • Predict the products
      05:16
    • General Reactions
      05:04

    Malonic Ester Synthesis

    • General Reactions
      01:25
    • Predict the Products
      04:09

    Condensation Reactions

    • Condensation Reactions
      05:53

    Aldol Condensation

    • General Features
      11:07

    Crossed Aldol Condensation

    • Crossed Aldol
      09:51

    Claisen-Schmidt Reaction

    • Predict the Major Product
      02:28
    • Claisen-Schmidt Reaction
      02:10

    Claisen Condensation

    • Claisen Condensation
      08:28

    Intramolecular Condensation

    • Diesters (Dieckmann Condensation)
      03:27
    • Diketones
      05:52

    Conjugate Addition of Enones

    • 1,2 vs 1,4 Addition
      09:23

    The Michael Reaction

    • General Mechanism
      03:27
    • General Reaction
      02:34

    Robinson Annulation

    • Predict the Major Product
      05:00
    • Robinson Annulation
      04:12

    Naming Amines

    • Naming Primary Amines
      06:50
    • Primary Amines as Substituents
      02:58
    • Naming Secondary and Tertiary Amines
      01:57

    Amine Alkylation

    • General Reaction
      03:51
    • Propose a Synthesis
      03:46
    • Mechanism
      03:54

    Gabriel Synthesis

    • Mechanism
      05:42
    • General Reaction
      04:53

    Amines by Reduction

    • The Primary Amines Flowchart
      09:12
    • Making Amine Precursors
      03:22

    Nitrogenous Nucleophiles

    • Four Ways to Make a Primary Amine Precursor
      07:11
    • Provide the Major Product
      01:30

    Reductive Amination

    • Reductive Amination
      07:12
    • Provide the Major Product
      03:07

    Curtius Rearrangement

    • Propose a Synthesis
      04:46
    • General Mechanism
      10:14

    Hofmann Rearrangement

    • Mechanism
      07:18
    • General Reaction
      02:51

    Diazonium Compounds – Replacements Reactions

    • Replacement Reactions
      06:59

    Diazo Compounds – Sequence Groups

    • Sequence Groups
      05:04

    Diazonium Compounds – Proposing Aromatic Synthesis

    • Synthesize the target molecule
      04:14
    • Synthesize the target molecule
      07:55
    • Proposing Aromatic Synthesis
      00:43