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Organic Chemistry Key Skills: Structured Study Guide (Chem 8A)

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Lewis Structure

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

Skeletal Structure

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

Condensed Structural Formula

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

Formal Charges

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

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

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

Functional Groups

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

Alkyl Groups

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

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

Naming Amines

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

Chirality

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

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

Optical Activity

  • Specific rotation vs. observed rotation.
    05:43

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

Chair Flip

  • The 3 important factors when drawing chairs
    05:12

Equatorial Preference

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

Naming Alkenes

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

Stability of Alkenes

  • Heat of Combustion
    02:55
  • Understanding trends of alkene stability.
    04:28

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

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

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

Acid-Catalyzed Hydration

  • General properties of acid-catalyzed hydration.
    06:32
  • Acid-catalyzed hydration mechanism
    06:34

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

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

E2 Mechanism

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

The E1 Mechanism

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

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