Carey 8th Edition - Organic Chemistry Tutoring Videos

ISBN: 978-0077354770
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Carey (8th) Topics and Chapters that we cover

Ch. 1 - Structure Determines Properties (Part 1)

Intro to Organic Chemistry
Atomic Structure
Octet Rule
Bonding Preferences
Formal Charges
Skeletal Structure
Lewis Structure

Ch. 1 - Structure Determines Properties (Part 2)

Condensed Structural Formula
Degrees of Unsaturation
Constitutional Isomers
Resonance Structures
Hybridization
Molecular Geometry
Electronegativity
Functional Groups
Reaction Mechanism
Acids and Bases
Equilibrium Constant
pKa
Acid Base Equilibrium
Ranking Acidity

Ch. 2 - Alkanes and Cycloalkanes: Introduction to Hydrocarbons

Wave Function
Molecular Orbitals
Sigma and Pi Bonds
IUPAC Naming
Alkyl Groups
Naming Cycloalkanes
Naming Bicyclic Compounds
Naming Alkyl Halides
Intermolecular Forces
How To Determine Solubility
Oxidizing and Reducing Agents

Ch. 3 - Alkanes and Cycloalkanes: Introduction to Stereochemistry

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
Calculating Energy Difference Between Chair Conformations
A-Values
Decalin

Ch. 4 - Alcohols and Alkyl Halides (Part.1)

Functional Groups
Naming Alkyl Halides
Naming Alcohols
Hammond Postulate
Carbocation Stability
Carbocation Intermediate Rearrangements
Nucleophilic Substitution
Good Leaving Groups
SN2 Reaction
SN1 reaction
Substitution Comparison
Leaving Group Conversions - Using HX
Leaving Group Conversions - SOCl2 and PBr3
Leaving Group Conversions - Sulfonyl Chlorides
Leaving Group Conversions Summary

Ch. 4 - Alcohols and Alkyl Halides (Part.2)

Radical Reaction
Radical Stability
Free Radical Halogenation
Energy Diagram
Gibbs Free Energy
Enthalpy
Entropy
Radical Selectivity
Calculating Radical Yields
Radical Synthesis

Ch. 5 - Structure and Preparation of Alkenes: Elimination Reactions

Naming Alkenes
Cis vs Trans
E2 Mechanism
Beta Hydrogen
E2 - Anti-Coplanar Requirement
E2 - Cumulative Practice
E1 Reaction
Alkene Stability
Zaitsev Rule
Dehydrohalogenation
Dehydration Reaction

Ch. 6 - Addition Reactions of Alkenes

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

Ch.7 - Chirality

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
Optical Activity
Enantiomeric Excess
Calculations with Enantiomeric Percentages
Non-Carbon Chiral Centers

Ch. 8 - Nucleophilic Substitution

Nucleophilic Substitution
Good Leaving Groups
SN2 Reaction
SN1 reaction
Substitution Comparison
Solvents
Leaving Groups
Nucleophiles and Basicity
SN1 SN2 E1 E2 Chart (Big Daddy Flowchart)
Cumulative Substitution/Elimination

Ch. 9 - Alkynes

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

Ch. 10 - Conjugation in Alkadienes and Allylic Systems

Conjugation Chemistry
Stability of Conjugated Intermediates
Molecular Orbital Theory
Drawing Atomic Orbitals
Drawing Molecular Orbitals
HOMO LUMO
Orbital Diagram: 3-atoms- Allylic Ions
Allylic Halogenation
Orbital Diagram: 4-atoms- 1,3-butadiene
Pericyclic Reaction
Thermal Cycloaddition Reactions
Conjugated Hydrohalogenation (1,2 vs 1,4 addition)
Diels-Alder Reaction
Diels-Alder Forming Bridged Products
Diels-Alder Retrosynthesis

Ch. 11 - Arenes and Aromaticity

Aromaticity
Naming Benzene Rings
Birch Reduction
Side-Chain Halogenation
Side-Chain Oxidation
Huckel's Rule
Pi Electrons
Aromatic Hydrocarbons
Annulene
Aromatic Heterocycles
Frost Circle
Acidity of Aromatic Hydrocarbons
Basicity of Aromatic Heterocycles
Ionization of Aromatics

Ch. 12 - Reactions of Aromatic Compounds

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
Limitations of Friedel-Crafts Alkyation
Advantages of Friedel-Crafts Acylation
Wolff Kishner Reduction
Blocking Groups - Sulfonic Acid
EAS: Synergistic and Competitive Groups
EAS: Sequence Groups
EAS: Retrosynthesis
Side-Chain Halogenation
Side-Chain Oxidation
Birch Reduction
EAS: Sequence Groups
EAS: Retrosynthesis
Nucleophilic Aromatic Substitution
Benzyne

Ch. 13 - Spectroscopy

Purpose of Analytical Techniques
Infrared Spectroscopy
Infrared Spectroscopy Table
IR Spect: Drawing Spectra
IR Spect: Extra Practice
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
NMR Practice
Carbon NMR
Structure Determination without Mass Spect
Mass Spectrometry
Mass Spect: Fragmentation
Mass Spect: Isotopes

Ch. 14 - Organometallic Compounds

Nucleophilic Addition
Preparation of Organometallics
Grignard Reaction
Protecting Alcohols from Organometallics
Organometallic Cumulative Practice
Carbene

Ch. 15 - Alcohol, Diols, and Thiols

Alcohol Synthesis
Oxidizing and Reducing Agents
Reducing Agent
Oxidizing Agent
Dihydroxylation
Epoxide Reactions
Fischer Esterification (Simplified)
Naming Thiols
Thiol Reactions

Ch. 16 - Ethers, Epoxides, and Sulfides

Alcohol Nomenclature
Naming Ethers
Naming Epoxides
Naming Thiols
Making Ethers - Alkoxymercuration
Williamson Ether Synthesis
Making Ethers - Alcohol Condensation
Making Ethers - Alkoxymercuration
Making Ethers - Acid-Catalyzed Alkoxylation
Making Ethers - Cumulative Practice
Alcohol Protecting Groups
t-Butyl Ether Protecting Groups
Silyl Ether Protecting Groups
Making Ethers - Alcohol Condensation
Making Ethers - Alkoxymercuration
Making Ethers - Acid-Catalyzed Alkoxylation
Ether Cleavage
Epoxidation
Epoxide Reactions
Sharpless Epoxidation
Sulfide Oxidation

Ch. 17 - Aldehydes and Ketones: Nucleophilic Addition to the Carbonyl Group

Naming Aldehydes
Naming Ketones
Oxidizing and Reducing Agents
Oxidation of Alcohols
Ozonolysis
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
Wittig Reaction
Ketone and Aldehyde Synthesis Reactions

Ch. 18 - Carboxylic Acids

Naming Carboxylic Acids
Diacid Nomenclature
Carboxylation
Fischer Esterification (Simplified)
Decarboxylation Mechanism

Ch. 19 - Carboxylic Acids Derivatives

Naming Esters
Acid Chloride Nomenclature
Naming Anhydrides
Naming Nitriles
Naming Amides
Carboxylic Acid Derivatives
Nucleophilic Acyl Substitution
Carboxylic Acid to Acid Chloride
Fischer Esterification
Acid-Catalyzed Ester Hydrolysis
Saponification
Transesterification
Lactones, Lactams and Cyclization Reactions
Nitrile to Ketone

Ch. 20 - Enols and Enolates

Tautomerization
Enolate
Overview of Alpha-Alkylations and Acylations
Enolate Alkylation and Acylation
Enamine Alkylation and Acylation
Tautomers of Dicarbonyl Compounds
Beta-Dicarbonyl Synthesis Pathway
Acetoacetic Ester Synthesis
Malonic Ester Synthesis
Acid-Catalyzed Alpha-Halogentation
Base-Catalyzed Alpha-Halogentation
Haloform Reaction
Hell-Volhard-Zelinski Reaction
Condensation Reactions
Aldol Condensation
Directed Condensations
Crossed Aldol Condensation
Claisen-Schmidt Condensation
Claisen Condensation
Intramolecular Aldol Condensation
Conjugate Addition
Michael Addition
Robinson Annulation

Ch. 21 - Amines

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

Ch. 22 - Phenols

Phenol Acidity
Cope Rearrangement
Claisen Rearrangement

Ch. 23 - 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 - Aldose-Ketose Rearrangement
Monosaccharides - Acylation
Glycoside
Monosaccharides - N-Glycosides
Monosaccharides - Reduction (Alditols)
Monosaccharides - Weak Oxidation (Aldonic Acid)
Reducing Sugars
Monosaccharides - Strong Oxidation (Aldaric Acid)
Monosaccharides - Oxidative Cleavage
Monosaccharides - Kiliani-Fischer
Monosaccharides - Wohl Degradation
Disaccharide
Polysaccharide

Ch. 25 - 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

Carey 8th Edition Solutions

Convert each of the following to a Newman Projection along the C2-C3 bond

Watch Solution

Sabinene and Δ3-carene are isomeric natural products with the molecular formula C10H16. (b) Ozonolysis of Δ3-carene gives compound B. What is the structure of Δ 3-carene?

Watch Solution

Sabinene and Δ3-carene are isomeric natural products with the molecular formula C10H16. (a) Ozonolysis of sabinene followed by hydrolysis in the presence of zinc gives compound A. What is the structure of sabinene? What other compound is formed on ozonolysis?

Watch Solution

East Indian sandalwood oil contains a hydrocarbon given the name santene (C9H14). Ozonolysis of santene gives compound A. What is the structure of santene?

Watch Solution

Compound A (C7H13Br) is a tertiary bromide. On treatment with sodium ethoxide in ethanol, A is converted into B (C7H12). Ozonolysis of B gives C as the only product. Deduce the structures of A and B. What is the symbol for the reaction mechanism by which A is converted to B under the reaction conditions?

Watch Solution

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