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Organic Chemistry: Structure, Bonding, and Reactivity – Study Notes (Chapters 1–9)

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What is Organic Chemistry?

  • Organic molecules in your everyday life.
    02:08
  • Identifying organic molecules
    02:17

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

Formal Charges

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

Lewis Structure

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

Condensed Structural Formula

  • How to draw condensed mixed structures.
    05:21
  • How to interpret condensed structures.
    06:06

Constitutional Isomers

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

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

Functional Groups

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

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

Equilibrium Constant and pKa

  • The pH scale vs. the pKa scale.
    02:15
  • The relationship between equilibrium constant and pKa.
    02:19
  • Why we use pKa instead of pH.
    01:46

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

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

Naming Bicyclic Compounds

  • How to name a bridged bicyclic
    04:39
  • The two types of bicyclic molecules
    01:55
  • How to name a fused bicyclic
    03:27

Naming Alkyl Halides

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

Naming Alcohols

  • How to name alcohols
    01:01
  • Name the following compound
    03:59
  • Old school vs. new school naming
    03:03

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
    09:00

A-Values

  • Calculating Chair Equilibrium
    06:27

Intro to Redox

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

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

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

Overview of Chemical Reactions

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

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

Enthalpy

  • How to calculate enthalpy using bond dissociation energies.
    04:09
  • Calculating Enthalpies
    04:38

Entropy

  • 3 ways to increase entropy.
    07:11
  • Explaining what entropy is.
    02:46

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

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

Hammond Postulate

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

Substitution Comparison

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

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

Functional Groups

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

Functional Groups

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

Functional Groups

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

Functional Groups

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

Nucleophilic Acyl Substitution

  • NAS - The Three Rules
    09:32

Acid-Base Properties of Amino Acids

  • Why Amino Acids Exist as Zwitterions
    04:41
  • Determining Predominant Forms
    07:57
  • Predicting Predominant Form of Lysine
    03:57

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

Equilibrium Constant and pKa

  • The pH scale vs. the pKa scale.
    02:15
  • The relationship between equilibrium constant and pKa.
    02:19
  • Why we use pKa instead of pH.
    01:46

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