McMurry 9th Edition - Organic Chemistry Tutoring Videos

ISBN: 978-1305080485
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McMurry (9th) Topics and Chapters that we cover

Ch.1 - Structure and Bonding (Part 1)

Intro to Organic Chemistry
Atomic Structure
Wave Function
Molecular Orbitals
Sigma and Pi Bonds
Octet Rule
Bonding Preferences
Formal Charges
Skeletal Structure

Ch.1 - Structure and Bonding (Part 2)

Lewis Structure
Condensed Structural Formula
Degrees of Unsaturation
Constitutional Isomers
Hybridization
Molecular Geometry

Ch.2 - Polar Colvalent Bonds: Acids and Bases

Electronegativity
Intermolecular Forces
How To Determine Solubility
Resonance Structures
Organic Chemistry Reactions
Reaction Mechanism
Acids and Bases
Equilibrium Constant
pKa
Acid Base Equilibrium
Ranking Acidity

Ch. 3 and 4 - Alkanes, Cycloalkanes and Their Stereochemistry

Functional Groups
IUPAC Naming
Alkyl Groups
Naming Cycloalkanes
Naming Alkyl Halides
Naming Bicyclic Compounds
Conformational Isomers
Newman Projections
Drawing Newman Projections
Barrier To Rotation
Ring Strain
Axial vs Equatorial
Cis vs Trans Conformations
Chair Flip
Equatorial Preference
Calculating Energy Difference Between Chair Conformations
A-Values
Decalin

Ch.5 - Stereochemistry at Tetrahedral Centers

Constitutional Isomers vs. Stereoisomers
Chirality
Test 1: Plane of Symmetry
Test 2: Stereocenter Test
R and S Configuration
Enantiomers vs. Diastereomers
Atropisomers
Meso Compound
Test 3: Disubstituted Cycloalkanes
What is the Relationship Between Isomers?
Fischer Projection
R and S of Fischer Projections
R and S Configuration
Optical Activity
Enantiomeric Excess
Non-Carbon Chiral Centers

Ch.6 - An Overview of Organic Synthesis

Reaction Mechanism
Energy Diagram
Gibbs Free Energy
Enthalpy
Entropy

Ch.7 - Alkenes: Structure and Reactivity

Alkene Stability
Degrees of Unsaturation
Naming Alkenes
Cis vs Trans
Carbocation Stability
Carbocation Intermediate Rearrangements
Hammond Postulate
Addition Reaction
Markovnikov
Hydrohalogenation

Ch.8 - Alkenes: Reactions and Synthesis

Addition Reaction
Markovnikov
Hydrohalogenation
Acid-Catalyzed Hydration
Oxymercuration
Hydroboration
Hydrogenation
Halogenation
Halohydrin
Carbene
Epoxidation
Dihydroxylation
Ozonolysis
Ozonolysis
Oxidative Cleavage
Free Radical Polymerization

Ch.9 - Alkynes: An Introduction to Organic Synthesis

Naming Alcohols
Double Elimination
Acetylide
Hydrogenation of Alkynes
Alkyne Hydrohalogenation
Alkyne Halogenation
Alkyne Hydration
Alkyne Hydroboration
Alkyne Oxidative Cleavage
Oxidation of Alcohols
Oxidative Cleavage
Alkynide Synthesis

Ch.10 - Organohalides

Radical Reaction
Radical Stability
Free Radical Halogenation
Radical Selectivity
Calculating Radical Yields
Allylic Bromination
Radical Synthesis
Leaving Group Conversions - Using HX
Leaving Group Conversions - SOCl2 and PBr3
Leaving Group Conversions - Sulfonyl Chlorides
Leaving Group Conversions Summary
Nucleophilic Addition
Grignard Reaction
Preparation of Organometallics
Oxidizing and Reducing Agents

Ch.11 - Reactions of Alkyl Halides: Nucleophilic Substitution (Part 1)

Nucleophilic Substitution
Good Leaving Groups
SN2 Reaction
SN1 reaction
Substitution Comparison

Ch.11 - Reactions of Alkyl Halides: Eliminations (Part 2)

E2 Mechanism
Beta Hydrogen
E2 - Anti-Coplanar Requirement
E2 - Cumulative Practice
E1 Reaction
Solvents
Leaving Groups
Nucleophiles and Basicity
SN1 SN2 E1 E2 Chart (Big Daddy Flowchart)
Cumulative Substitution/Elimination
Naming Alkenes
Alkene Stability
Zaitsev Rule

Ch. 12 - Structure Determination: Mass Spect and Infrared Spectrometry

Purpose of Analytical Techniques
Infrared Spectroscopy
Infrared Spectroscopy Table
IR Spect: Drawing Spectra
IR Spect: Extra Practice
Mass Spectrometry
Mass Spect: Fragmentation
Mass Spect: Isotopes

Ch. 13 - Structure Determination: Nuclear Magnetic Resonance

NMR Spectroscopy
1H NMR: Number of Signals
1H NMR: Q-Test
1H NMR: E/Z Diastereoisomerism
H NMR Table
1H NMR: Spin-Splitting (N + 1) Rule
1H NMR: Spin-Splitting Simple Tree Diagrams
1H NMR: Spin-Splitting Complex Tree Diagrams
1H NMR: Spin-Splitting Patterns
NMR Integration
Structure Determination without Mass Spect
NMR Practice
Carbon NMR

Ch. 14 - Conjugated Compounds and UV Spectroscopy

Conjugation Chemistry
Stability of Conjugated Intermediates
Allylic Halogenation
Conjugated Hydrohalogenation (1,2 vs 1,4 addition)
Diels-Alder Reaction
Diels-Alder Forming Bridged Products
Diels-Alder Retrosynthesis

Ch. 15 - Benzene and Aromaticity

Aromaticity
Naming Benzene Rings
Huckel's Rule
Pi Electrons
Aromatic Hydrocarbons
Annulene
Aromatic Heterocycles
Acidity of Aromatic Hydrocarbons
Basicity of Aromatic Heterocycles
Ionization of Aromatics

Ch. 16 - Chemistry of Benzene: Electrophilic Aromatic Substitution

Electrophilic Aromatic Substitution
Benzene Reactions
EAS: Halogenation Mechanism
EAS: Nitration Mechanism
EAS: Friedel-Crafts Alkylation Mechanism
EAS: Friedel-Crafts Acylation Mechanism
EAS: Any Carbocation Mechanism
Electron Withdrawing Groups
EAS: Ortho vs. Para Positions
Acylation of Aniline
Limitations of Friedel-Crafts Alkyation
Advantages of Friedel-Crafts Acylation
Blocking Groups - Sulfonic Acid
EAS: Synergistic and Competitive Groups
Side-Chain Halogenation
Side-Chain Oxidation
EAS: Sequence Groups
EAS: Retrosynthesis
EAS: Retrosynthesis
Birch Reduction
Nucleophilic Aromatic Substitution
Benzyne
Phenol Acidity

Ch. 17 - Alcohols and Phenols

Alcohol Nomenclature
Oxidizing and Reducing Agents
Oxidation of Alcohols
Reducing Agent
Nucleophilic Addition
Preparation of Organometallics
Grignard Reaction
Protecting Alcohols from Organometallics
Organometallic Cumulative Practice
Dehydration Reaction
POCl3 Dehydration
Fischer Esterification
Alcohol Protecting Groups
t-Butyl Ether Protecting Groups
Silyl Ether Protecting Groups

Ch. 18 - Ethers, Epoxides; Thiols, Sulfides

Naming Ethers
Williamson Ether Synthesis
Making Ethers - Alcohol Condensation
Making Ethers - Alkoxymercuration
Making Ethers - Acid-Catalyzed Alkoxylation
Making Ethers - Cumulative Practice
Ether Cleavage
Claisen Rearrangement
Naming Epoxides
Epoxidation
Epoxide Reactions
Naming Thiols
Sharpless Epoxidation
Thiol Reactions
Sulfide Oxidation

Ch. 19 - Aldehydes and Ketones: Nucleophilic Addition

Naming Aldehydes
Naming Ketones
Oxidizing and Reducing Agents
Oxidizing Agent
Ozonolysis
Reducing Agent
DIBAL
Alkyne Hydration
Nucleophilic Addition
Cyanohydrin
Organometallics on Ketones
Overview of Nucleophilic Addition of Solvents
Hydrates
Hemiacetal
Acetal
Acetal Protecting Group
Thioacetal
Imine vs Enamine
Addition of Amine Derivatives
Wolff Kishner Reduction
Acid Chloride to Ketone
Wittig Reaction
Ketone and Aldehyde Synthesis Reactions
Conjugate Addition

Ch. 20 - Carboxylic Acids and Nitriles

Naming Carboxylic Acids
Diacid Nomenclature
Naming Nitriles
Carboxylation
Nitrile to Ketone

Ch. 21 - Carboxylic Acid Derivatives: Nucleophilic Acyl Substitution

Acid Chloride Nomenclature
Naming Anhydrides
Naming Esters
Naming Amides
Carboxylic Acid Derivatives
Nucleophilic Acyl Substitution
Carboxylic Acid to Acid Chloride
Fischer Esterification
Acid-Catalyzed Ester Hydrolysis
Saponification
Transesterification
Grignard Reaction
Lactones, Lactams and Cyclization Reactions
Decarboxylation Mechanism

Ch. 22 - Carbonyl Alpha-Substitution Reactions

Tautomerization
Tautomers of Dicarbonyl Compounds
Enolate
Acid-Catalyzed Alpha-Halogentation
Base-Catalyzed Alpha-Halogentation
Haloform Reaction
Hell-Volhard-Zelinski Reaction
Overview of Alpha-Alkylations and Acylations
Enolate Alkylation and Acylation
Beta-Dicarbonyl Synthesis Pathway
Acetoacetic Ester Synthesis
Malonic Ester Synthesis

Ch. 23 - Carbonyl Condensations

Condensation Reactions
Aldol Condensation
Crossed Aldol Condensation
Claisen-Schmidt Condensation
Claisen Condensation
Intramolecular Aldol Condensation
Conjugate Addition
Michael Addition
Enamine Alkylation and Acylation
Robinson Annulation

Ch. 24 - Amines and Heterocycles

Naming Amines
Amine Alkylation
Amines by Reduction
Nitrogenous Nucleophiles
Reductive Amination
Gabriel Synthesis
Curtius Rearrangement
Hofmann Rearrangement
Hofmann Elimination
Diazo Replacement Reactions
Acylation of Aniline
Diazo Sequence Groups
Diazo Retrosynthesis

Ch. 25 - Biomolecules: Carbohydrates

Monosaccharide
Monosaccharides - D and L Isomerism
Monosaccharides - Drawing Fischer Projections
Monosaccharides - Common Structures
Monosaccharides - Forming Cyclic Hemiacetals
Monosaccharides - Cyclization
Monosaccharides - Haworth Projections
Mutarotation
Epimerization
Monosaccharides - Alkylation
Monosaccharides - Acylation
Glycoside
Monosaccharides - Reduction (Alditols)
Monosaccharides - Weak Oxidation (Aldonic Acid)
Reducing Sugars
Monosaccharides - Strong Oxidation (Aldaric Acid)
Monosaccharides - Osazones
Monosaccharides - Kiliani-Fischer
Monosaccharides - Wohl Degradation
Disaccharide
Polysaccharide

Ch. 26 - Biomolecules: Amino Acids, Peptides, and Proteins

Proteins and Amino Acids
L and D Amino Acids
Polar Amino Acids
Amino Acid Chart
Acid-Base Properties of Amino Acids
Isoelectric Point

Ch. 27 - Biomolecules: Lipids

Claisen Rearrangement

Ch. 28 - Biomolecules: Nucleic Acids

Claisen Rearrangement

Ch. 29 - The Organic Chemistry of Metabolic Pathways

Claisen Rearrangement

Ch. 30 - Orbitals and Organic Chemistry: Pericyclic Reactions

Molecular Orbital Theory
Drawing Atomic Orbitals
Drawing Molecular Orbitals
HOMO LUMO
Orbital Diagram: 3-atoms- Allylic Ions
Orbital Diagram: 4-atoms- 1,3-butadiene
Orbital Diagram: 5-atoms- Allylic Ions
Orbital Diagram: 6-atoms- 1,3,5-hexatriene
Orbital Diagram: Excited States
Pericyclic Reaction
Thermal Electrocyclic Reactions
Photochemical Electrocyclic Reactions
Cumulative Electrocyclic Problems
Thermal Cycloaddition Reactions
Photochemical Cycloaddition Reactions
Sigmatropic Rearrangement
Cope Rearrangement
Claisen Rearrangement