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Organic Chemistry Study Notes: Structure, Bonding, Acids/Bases, Functional Groups, and Stereochemistry

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Formal Charges

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

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

pKa Values

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

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

Factors Affecting Acidity

  • Which of the oxides is the most basic?
    00:30
  • The 3 factors that determine the strength of inductive effects.
    03:09
  • Using Inductive Effect to determine acidity
    01:54

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

Molecular Geometry

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

Electronegativity

  • Differences between ionic, polar and covalent bonds
    11:33

Intermolecular Forces

  • How dipole-dipole forces work.
    01:46
  • How IMFs are related to melting and boiling points.
    03:08
  • How Van der Waals forces work.
    03:01

Functional Groups

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

Alkane Nomenclature

  • Naming the root chain
    01:02
  • Provide the IUPAC name for the following alkane
    07:08
  • The different parts of an IUPAC name
    03:43

Alkyl Groups

  • Name the following alkane
    02:33
  • Understanding Non-IUPAC Substituents
    06:42
  • Name the following alkane
    03:56

Skeletal Structure

  • How bondline is different from Lewis Structures.
    04:03
  • Conversion of ethanol from electron dot to bondline
    01:50

Lewis Structure

  • Drawing the Lewis Structure for N2H4.
    04:12
  • How to use Organic Chemistry to make Lewis Structures easier.
    03:49

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

Radical Initiators

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

Radical Stability

  • The radical stability trend.
    03:43
  • Determine which of the following radicals is the most stable.
    03:25

Radical Selectivity

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

Hammond Postulate

  • Defining the Hammond Postulate.
    01:30
  • Bromination explains the Hammond Postulate.
    02:58
  • Chlorination explains the Hammond Postulate.
    05:23

Constitutional Isomers

  • Isomeric Relationships
    03:28
  • Using the flowchart to determine isometric relationships.
    05:02
  • Isomeric Relationships
    02:56

Types of Isomers

  • Determining when molecules are conformers.
    01:39
  • Determining when molecules are different.
    03:51
  • Determining when molecules are constitutional isomers.
    01:33

Chirality

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

Chirality Test 1 - Internal Line of Symmetry

  • Determining Chirality with Plane of Symmetry
    00:25
  • Determining Chirality with Plane of Symmetry
    01:10
  • How and when to use the internal line of symmetry test.
    01:25

Chirality Test 2 - Stereocenters

  • Determining Chirality using Stereocenter
    02:25
  • Determining Chirality using Stereocenter
    00:36
  • The difference between chiral and trigonal centers.
    02:38

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

Meso Compounds

  • Defining meso compounds.
    01:40
  • The 3 rules of meso compounds.
    04:10
  • Which of the following molecules are meso?
    03:44

Chirality Test 3 - Disubstituted Cycloalkanes Shortcuts

  • Is the following disubstituted cyclobutane chiral?
    00:35
  • Three types of disubstituted cycloalkanes
    03:52
  • Is the following disubstituted cyclopropane chiral?
    00:22

Isometric Relationships

  • Same atoms, same connectivity, 1 chiral center.
    01:40
  • Same atoms, same connectivity, 1 or more trigonal centers.
    02:05
  • Different atoms or different connectivity.
    01:41

Fischer Projection

  • Introduction to different projections.
    01:15
  • How to convert Fischer projections into bondline structures
    05:45
  • Convert the following Fischer projection into bondline structure.
    03:38

Fischer Configurations

  • R and S rule for Fischer Projections.
    02:32
  • Determining Absolute Configurations
    05:25

Optical Activity

  • Specific rotation vs. observed rotation.
    05:43

Enantiomeric Excess

  • Calculating Enantiomeric Excess and Observed Rotation
    00:50
  • How to calculate enantiomeric excess.
    04:21
  • Calculating Enantiomeric Excess and Observed Rotation
    03:59

Calculations with Enantiomeric Percentages

  • Calculating EE, percent of each enantiomer, and sketching mixture
    03:08
  • How to solve for the percentage of each enantiomer.
    03:23

Naming Alkyl Halides

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

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

Leaving Groups

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

The SN2 Mechanism

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

SN1 Mechanism

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

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

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

Nucleophiles and Basicity

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

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

Substitution Comparison

  • How do we predict if the mechanism is SN1 or SN2?
    03:32

Naming Alkenes

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

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

E2 Mechanism

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

Recognizing Different β-Hydrogens

  • Identify the number of unique products
    02:08
  • Identify the number of unique products
    03:19
  • Identify the number of unique products
    02:02

The Anti-Coplanar Requirement

  • The Anti-Coplanar Requirement
    03:19
  • Identify the completion of E2 mechanisms
    03:39
  • Identify the completion of E2 mechanisms
    01:09

E2 - Cumulative Practice

  • E2 Cumulative Intro
    00:27

The E1 Mechanism

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

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

Cumulative Substitution/Elimination

  • Intro to Substitution/Elimination Problems
    00:38

Stability of Alkenes

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

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

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

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

Ozonolysis Full Mechanism

  • Predict the products and show the mechanism:
    12:11
  • General Mechanism:
    07:48
  • Reductive Workup Mechanism:
    03:16

Oxidative Cleavage

  • General properties of strong oxidative cleavage.
    06:00

Radical Polymerization

  • General features of Radical Polymerization.
    02:44
  • The mechanism of Radical Polymerization.
    03:28
  • Use the polymerization mechanism to draw the polymer formula for the following compound.
    02:20

Alkene Metathesis

  • Guided course
    Alkene Metathesis Example 1
    1:47
  • Guided course
    Alkene Metathesis Example 4
    1:41
  • Guided course
    Alkene Metathesis Example 2
    3:04

Double Dehydrohalogenation (Alkyne Synthesis)

  • General features of double dehydrohalogenation.
    02:20
  • Supply the mechanism and product for the following reaction.
    02:26
  • The double dehydrohalogenation mechanism.
    04:03

NMR Spectroscopy

  • General NMR Features
    10:06

1H NMR: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 (N + 1) Rule

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

NMR Integration

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

Carbon NMR

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