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
Basics of Atomic Structure
Wave Functions
Molecular Orbitals
Properties of Bonds
Octet Rule
Bonding Preferences
Formal Charges
Bondline Structure

Ch.1 - Structure and Bonding (Part 2)

Lewis Structures
Condensed Structures
Index of Hydrogen Deficiency
Constitutional Isomers
Hybrid Orbitals
VSEPR Theory and Molecular Geometry

Ch.2 - Polar Colvalent Bonds: Acids and Bases

Electronegativity and Dipoles
Intermolecular Forces
Solubility
Resonance Structures
Overview of Reactions
Introduction to Mechanisms
Acid and Base Definitions
Equilibrium Constant
Comparing Acidity with pKas
Predicting Acid and Base Equilibrium
Factors Affecting Acidity Overview

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

Functional Groups
Alkane Nomenclature
Common Substituent Nomenclature
Cycloalkane Nomenclature
Fused and Bridged Bicyclic Nomenclature
Sigma Bond Rotation
Conformations of Newman Projections
Drawing Newman Projections
Calculating Energy of Newman Projection Rotation
Stability of Small Rings
Cyclohexane - Axial and Equatorial Positions
Cyclohexane - Cis and Trans
Cyclohexane - Equivalent Chairs
Cyclohexane - Equatorial Preference
Cyclohexane- Calculating Flip Energy
Decalins

Ch.5 - Stereochemistry at Tetrahedral Centers

Constitutional Isomers vs. Stereoisomers
Definition of Chirality
Test 1: Plane of Symmetry
Test 2: Stereocenter Test
The R and S Naming System
Enantiomers vs. Diastereomers
Atropisomers
Meso Compounds
Test 3: Disubstituted Cycloalkanes
What is the Relationship Between Isomers?
Fischer Projections
The R and S Naming System
Optical Activity: Specific vs. Observed Rotation
Non-Carbon Chiral Centers

Ch.6 - An Overview of Organic Synthesis

Introduction to Mechanisms
Free Energy Diagrams
Gibbs Free Energy
Enthalpy
Entropy

Ch.7 - Alkenes: Structure and Reactivity

Stability of Alkenes
Index of Hydrogen Deficiency
Alkene and Alkyne Nomenclature
Cis and Trans, E and Z Nomenclature
Carbocation Intermediate Stability
The Hammond Postulate
Addition General Mechanism
Markovnikov's Rule
Hydrohalogenation

Ch.8 - Alkenes: Reactions and Synthesis

Addition General Mechanism
Markovnikov's Rule
Hydrohalogenation
Acid-Catalyzed Hydration
Oxymercuration-Reduction
Hydroboration-Oxidation
Catalytic Hydrogenation
Halogenation
Halohydrin Formation
Carbenes and Cyclopropation
Epoxidation
Syn Vicinal Dihydroxylation
Ozonolysis
Ozonolysis to Yield Ketones
Strong Oxidative Cleavage
Radical Polymerization

Ch.9 - Alkynes: An Introduction to Organic Synthesis

Double Dehydrohalogenation
Terminal Alkynes and Alkynides
Overview of Alkyne Hydrogenation
Alkyne Additions
Alkyne Cleavage
Carbonyls Via Oxidation
Strong Oxidative Cleavage
Alkynide Multistep Synthesis

Ch.10 - Organohalides

Radical Initiation
Radical Stability
Radical Chain Reaction
Radical Selectivity
Calculating Radical Yields
Allylic Halogenation
Leaving Group Conversions
Nucleophilic Addition
Grignards and Organolithium Reactions
Preparation of Organometallics
Intro to Redox

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

Introduction to Substitution
Leaving Groups
SN2 Mechanism
SN1 Mechanism
Substitution Comparison

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

E2 - Mechanism Introduction
E2 - Recognizing Beta-Hydrogens
The E1 Mechanism
Solvents
Leaving Groups and Nucleophiles
The Big Daddy Flowchart (Determining Mechanisms)
Alkene and Alkyne Nomenclature
Stability of Alkenes
Zaitsev's Rule

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

Purpose of Analytical Techniques
IR Spect: General Features
IR Spect: Frequencies
IR Spect: Drawing Spectra
IR Spect: Extra Practice
Mass Spect: Introduction
Mass Spect: Fragmentation
Mass Spect: Isotopes

Ch. 13 - Structure Determination: Nuclear Magnetic Resonance

1H NMR: General Features
1H NMR: Number of Signals
1H NMR: Chemical Shifts
1H NMR: Spin-Splitting
1H NMR: Integration
13C NMR: General Features
Structure Determination without Mass Spect
1H NMR: Cumulative Practice

Ch. 14 - Conjugated Compounds and UV Spectroscopy

Introduction to Conjugation
Stability of Conjugated Intermediates
Allylic Halogenation
Conjugated Hydrohalogenation
Diels-Alder Reaction

Ch. 15 - Benzene and Aromaticity

Introduction to Aromaticity
Benzene Nomenclature
Four Tests of Aromaticity
Counting Pi Electrons
Aromaticity of Hydrocarbons
Aromaticity of Heterocycles

Ch. 16 - Chemistry of Benzene: Electrophilic Aromatic Substitution

EAS: Introduction
EAS: Reactions
EAS: Generating Electrophiles
EDGs and EWGs
EAS: Ortho vs. Para Positions
Protection of Aniline Derivatives
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
SNAr Mechanism
Benzyne Pathway
Acidity of Phenols

Ch. 17 - Alcohols and Phenols

Advanced Alcohol Nomenclature
Intro to Redox
Carbonyls Via Oxidation
Reduction
Nucleophilic Addition
Preparation of Organometallics
Grignards and Organolithium Reactions
Alcohol Protecting Groups with Organometallics
Acid-Catalyzed Dehydration
Dehydration with POCl3
Fischer Esterification

Ch. 18 - Ethers, Epoxides; Thiols, Sulfides

Ether Nomenclature
Making Ethers - Williamson Ether Synthesis
Cleavage of Ethers
Claisen Rearrangement
Epoxide Nomenclature
Epoxidation
Epoxide Ring Opening
Thiol and Sulfide Nomenclature
Reactions of Thiols
Oxidation of Sulfides

Ch. 19 - Aldehydes and Ketones: Nucleophilic Addition

Aldehyde Nomenclature
Ketone Nomenclature
Intro to Redox
Oxidation
Ozonolysis to Yield Ketones
Reduction
Aldehydes Via Reduction
Nucleophilic Addition
Cyanohydrins
Organometallics on Ketones
Overview of Nucleophilic Addition of Solvents
Hydrates
Hemiacetals
Acetals
Acetals as Protecting Groups
Thioacetals and Raney Nickel Reduction
Imines and Enamines
Addition of Amine Derivatives
Wolff-Kischner Reduction
The Wittig Reaction
Ketone and Aldehyde Synthesis Reactions
Conjugate Addition (1,2, vs. 1,4 Addition)

Ch. 20 - Carboxylic Acids and Nitriles

Carboxylic Acid Nomenclature
Nitrile Nomenclature
Carbonation of Grignard Reagents
Organometallics on Nitriles

Ch. 21 - Carboxylic Acid Derivatives: Nucleophilic Acyl Substitution

Anhydride Nomenclature
Ester Nomenclature
Amide Nomenclature
Carboxylic Acid Derivatives
Nucleophilic Substitution: The Three Rules
Carboxylic Acids to Acid Halides
Fischer Esterification
Acid-Catalyzed Ester Hydrolysis
Base-Catalyzed Ester Hydrolysis (Saponification)
Base-Catalyzed Transesterification
Grignards and Organolithium Reactions

Ch. 22 - Carbonyl Alpha-Substitution Reactions

Alpha-Carbons and Tautomerization
Tautomers of Dicarbonyl Compounds
Enolates
Electrophilic Alpha-Halogenations
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 Reaction
Claisen Condensation
Intramolecular Condensation
Conjugate Addition (1,2, vs. 1,4 Addition)
Michael Reaction
Robinson Annulation
Enamine Alkylation and Acylation

Ch. 24 - Amines and Heterocycles

Amine Nomenclature
Amines by Reduction
Nitrogenous Nucleophiles
Reductive Amination
Gabriel Synthesis
Curtius Rearrangement
Hofmann Rearrangement
Hofmann Elimination
Protection of Aniline Derivatives
Diazo Replacement Reactions
Diazo Sequence Groups
Diazo: Retrosynthesis

Ch. 25 - Biomolecules: Carbohydrates

Introduction to Carbohydrate Monosaccharides
Monosaccharides - D and L Isomerism
Monosaccharides - Drawing Fischer Projections
Monosaccharides - Common Structures
Monosaccharides - Forming Cyclic Hemiacetals
Monosaccharides - Cyclization
Monosaccharides - Haworth Projections
Monosaccharides - Mutorotation
Monosaccharides - Alkylation
Monosaccharides - Acylation
Monosaccharides - O-Glycosides
Monosaccharides - Reduction (Alditols)
Monosaccharides - Weak Oxidation (Aldonic Acid)
Monosaccharides - Reducing Sugars
Monosaccharides - Strong Oxidation (Aldaric Acid)
Monosaccharides - Kiliani-Fischer Synthesis
Monosaccharides - Wohl Degradation
Condensation into Disaccharides
Polysaccharides

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

Cope Rearrangement

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

Basics of MO Theory
Drawing Atomic Orbitals
Drawing Molecular Orbitals
FMOT: Finding 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
Intro to Pericyclic Reactions
Thermal Electrocyclic Reactions
Photochemical Electrocyclic Reactions
Cumulative Electrocyclic Problems
Thermal Cycloaddition Reactions
Photochemical Cycloaddition Reactions
Intro to Sigmatropic Shifts
Cope Rearrangement
Claisen Rearrangement