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Foundations of Organic Chemistry: Atomic Structure, Bonding, and Molecular Geometry

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Atomic Structure

  • Three rules about orbitals you need to know.
    02:54
  • Understanding the hydrogen isotopes.
    03:06
  • The difference between atomic numbers and atomic mass.
    01:44

Wave Function

  • Constructive vs. destructive interference.
    03:18
  • The probability of finding electrons in a given place.
    05:41

Molecular Orbital Theory

  • Sigma bond vs. pi bond, which is stronger?
    03:25
  • What’s the difference between sigma and pi bonds?
    02:19
  • What’s the difference between atomic and molecular orbitals?
    11:25

Sigma and Pi Bonds

  • Single bonds, double bonds, and triple bonds.
    06:00
  • Sigma bonds and pi bonds
    01:05
  • Sigma bonds and pi bonds
    00:59

Octet Rule

  • LCAO model proves why Noble gases are so stable.
    03:48
  • The most important parts of the periodic table for organic chemistry
    02:24
  • How Noble gases are related to the octet rule.
    01:05

Bonding Preferences

  • What is the difference between valence and octet electrons?
    02:04
  • Understanding the hydrogen isotopes.
    08:32
  • What is a valence electron?
    02:14

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

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

Overview of Chemical Reactions

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

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

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

Energy Diagram

  • Favorability and rate of Free Energy Diagrams
    01:14
  • Favorability and rate of Free Energy Diagrams
    00:34
  • Favorability and rate of Free Energy Diagrams
    02:18

Gibbs Free Energy

  • Intermediates vs. Transition States
    06:55
  • Breaking down the different terms of the Gibbs Free Energy equation.
    05:02

Hammond Postulate

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

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

Naming Cycloalkanes

  • Name the following alkane
    00:53
  • Determining Root Name
    00:18
  • Determining Root Name
    00:34

Constitutional Isomers

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

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

Skeletal Structure

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

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

Conformational Isomers

  • Understanding what a conformer is.
    03:29

Newman Projections

  • 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

Drawing Newman Projections

  • Step 6 to Drawing Newman Projections
    01:31
  • Step 5 to Drawing Newman Projections
    01:51
  • Step 3 to Drawing Newman Projections
    00:28

Barrier To Rotation

  • 4 Values You Should Memorize
    02:54
  • Determining energy cost of eclipsed interaction
    03:00

Ring Strain

  • Understanding Heat of Combustion
    01:11
  • What is torsional strain?
    02:00
  • Lowest Heat of Combustion
    02:34

Axial vs Equatorial

  • What is a chair conformation?
    01:05
  • How chairs flip from one conformation to another
    02:22
  • How chairs flip from one conformation to another
    04:26

Cis vs Trans Conformations

  • Is the following cyclohexane cis or trans?
    00:44
  • How to draw chairs.
    01:18
  • Is the following cyclohexane cis or trans?
    00:27

Equatorial Preference

  • Equatorial Preference
    04:02
  • Draw the following chair in the most stable conformation.
    03:17

Chair Flip

  • The 3 important factors when drawing chairs
    05:12

Calculating Energy Difference Between Chair Conformations

  • Explaining how A-Values are related to cyclohexane flip energy
    09:55

A-Values

  • Calculating Chair Equilibrium
    06:27

Decalin

  • How to determine the stability of a decalin.
    03:52
  • Draw the following decalin as a chair conformation in the most stable conformation.
    03:14

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

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 Reaction

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

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

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

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

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