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Organic Chemistry II (CHE251) Final Exam Review Topics – Structured Study Notes

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What is Organic Chemistry?

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

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

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

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

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

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

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

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

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

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

Alkene Stability

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

Zaitsev 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

Alcohol Nomenclature

  • Provide the correct common and IUPAC name.
    01:49
  • How to name polyols.
    01:47
  • Provide the correct common and IUPAC name.
    00:59

Oxidizing and Reducing Agents

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

Alkane Halogenation

  • Functionalizing Alkanes
    02:47

Radical Reaction

  • 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

Free Radical Halogenation

  • The one reaction that alkanes will actually undergo.
    02:05
  • Explaining the following problem.
    00:34
  • Show the entire chain reaction mechanism.
    04:08

Radical Selectivity

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

Allylic Bromination

  • Predict the product(s) of the following reaction.
    04:28
  • Mechanism of Allylic Bromination.
    00:54
  • The products of Allylic Chlorination.
    00:48

Anti Markovnikov Addition of Br

  • 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

Conjugation Chemistry

  • 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

Diels-Alder Reaction

  • General Features
    09:48

Electrophilic Aromatic Substitution

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

Benzene Reactions

  • EAS Reactions Overview
    11:50

EAS:Halogenation Mechanism

  • EAS Halogenation
    06:26

EAS:Nitration Mechanism

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

EAS:Friedel-Crafts Alkylation Mechanism

  • Friedel-Crafts Alkylation
    06:30

EAS:Friedel-Crafts Acylation Mechanism

  • Friedel-Crafts Acylation
    05:20

EAS:Any Carbocation Mechanism

  • Any Carbocation
    07:21

Electron Withdrawing Groups

  • Badass Activity Chart
    11:55
  • Activity and Directing Effects
    04:29

EAS:Ortho vs. Para Positions

  • Ortho, Para major products
    04:42

Limitations of Friedel-Crafts Alkyation

  • Limitations
    10:14

Advantages of Friedel-Crafts Acylation

  • Advantages
    06:05

Side-Chain Halogenation

  • Side-Chain Halogenations
    06:14

Side-Chain Oxidation

  • Benzylic Oxidation
    03:20
  • Which alkylbenzene would NOT yield benzoic acid, treated with KMnO4
    00:49

Reactions at Benzylic Positions

  • Guided course
    Reactions at Benzylic Positions Example 3
    1:12
  • Guided course
    Reactions at Benzylic Positions Example 2
    2:03
  • Guided course
    Reactions at Benzylic Positions Concept 1
    1:01

Nucleophilic Aromatic Substitution

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

Oxidation of Phenols to Quinones

  • Guided course
    Oxidation of Phenols to Quinones Concept 2
    1:57
  • Guided course
    Oxidation of Phenols to Quinones Concept 1
    1:47
  • Guided course
    Oxidation of Phenols to Quinones Example 1
    3:00

Cleavage of Phenyl Ethers

  • Guided course
    Cleavage of Phenyl Ethers Concept 1
    1:45
  • Guided course
    Cleavage of Phenyl Ethers Example 1
    1:57

Reactions of Pyrrole, Furan, and Thiophene

  • Guided course
    Reactions of Pyrrole, Furan, and Thiophene Concept 2
    3:45
  • Guided course
    Reactions of Pyrrole, Furan, and Thiophene Example 2
    1:31
  • Guided course
    Reactions of Pyrrole, Furan, and Thiophene Concept 1
    2:36

Directing Effects in Substituted Pyrroles, Furans, and Thiophenes

  • Guided course
    Directing Effects in Substituted Pyrroles, Furans, and Thiophenes Concept 2
    3:26
  • Guided course
    Directing Effects in Substituted Pyrroles, Furans, and Thiophenes Example 1
    1:20
  • Guided course
    Directing Effects in Substituted Pyrroles, Furans, and Thiophenes Concept 1
    2:02

Addition Reactions of Furan

  • Guided course
    Addition Reactions of Furan Example 1
    2:01
  • Guided course
    Addition Reactions of Furan Concept 1
    1:42
  • Guided course
    Addition Reactions of Furan Concept 2
    2:35

EAS Reactions of Pyridine

  • Guided course
    EAS Reactions of Pyridine Concept 3
    3:22
  • Guided course
    EAS Reactions of Pyridine Example 1
    1:18
  • Guided course
    EAS Reactions of Pyridine Concept 2
    2:53

SNAr Reactions of Pyridine

  • Guided course
    SNAr Reactions of Pyridine Concept 2
    1:07
  • Guided course
    SNAr Reactions of Pyridine Example 2
    1:04
  • Guided course
    SNAr Reactions of Pyridine Example 1
    3:57

Side-Chain Reactions of Substituted Pyridines

  • Guided course
    Side-Chain Reactions of Substituted Pyridines Concept 1
    2:36
  • Guided course
    Side-Chain Reactions of Substituted Pyridines Example 1
    1:32
  • Guided course
    Side-Chain Reactions of Substituted Pyridines Example 3
    1:57