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
Basics of Atomic Structure
Octet Rule
Bonding Preferences
Formal Charges
Bondline Structure
Lewis Structures

Ch. 1 - Structure Determines Properties (Part 2)

Condensed Structures
Index of Hydrogen Deficiency
Constitutional Isomers
Resonance Structures
Hybrid Orbitals
VSEPR Theory and Molecular Geometry
Electronegativity and Dipoles
Functional Groups
Introduction to Mechanisms
Acid and Base Definitions
Equilibrium Constant
Comparing Acidity with pKas
Predicting Acid and Base Equilibrium
Factors Affecting Acidity Overview

Ch. 2 - Alkanes and Cycloalkanes: Introduction to Hydrocarbons

Wave Functions
Molecular Orbitals
Properties of Bonds
Alkane Nomenclature
Common Substituent Nomenclature
Cycloalkane Nomenclature
Fused and Bridged Bicyclic Nomenclature
Alkyl Halide Nomenclature
Intermolecular Forces
Solubility
Intro to Redox

Ch. 3 - Alkanes and Cycloalkanes: Introduction to Stereochemistry

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
Cyclohexane- Calculating Flip Energy
Decalins

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

Functional Groups
Alkyl Halide Nomenclature
Alcohol Nomenclature
The Hammond Postulate
Carbocation Intermediate Stability
Introduction to Substitution
Leaving Groups
SN2 Mechanism
SN1 Mechanism
Substitution Comparison
Leaving Group Conversions

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

Radical Initiation
Radical Stability
Radical Chain Reaction
Free Energy Diagrams
Gibbs Free Energy
Enthalpy
Entropy
Radical Selectivity
Calculating Radical Yields
Radical Multistep Synthesis

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

Alkene and Alkyne Nomenclature
Cis and Trans, E and Z Nomenclature
E2 - Mechanism Introduction
E2 - Recognizing Beta-Hydrogens
E2: Cumulative Practice
The E1 Mechanism
Stability of Alkenes
Zaitsev's Rule
Dehydrohalogenation
Acid-Catalyzed Dehydration

Ch. 6 - Addition Reactions of Alkenes

Addition General Mechanism
Markovnikov's Rule
Hydrohalogenation
Radical Hydrohalogenation
Acid-Catalyzed Hydration
Oxymercuration-Reduction
Hydroboration-Oxidation
Catalytic Hydrogenation
Halogenation
Halohydrin Formation
Epoxidation
Regiospecificity of Acid-Catalyzed Ring Openings
Ozonolysis
Strong Oxidative Cleavage
Radical Polymerization

Ch.7 - Chirality

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
Optical Activity: Specific vs. Observed Rotation
Non-Carbon Chiral Centers

Ch. 8 - Nucleophilic Substitution

Introduction to Substitution
Leaving Groups
SN2 Mechanism
SN1 Mechanism
Substitution Comparison
Solvents
Leaving Groups and Nucleophiles
The Big Daddy Flowchart (Determining Mechanisms)

Ch. 9 - Alkynes

Alkene and Alkyne Nomenclature
Double Dehydrohalogenation
Terminal Alkynes and Alkynides
Overview of Alkyne Hydrogenation
Alkyne Additions
Alkyne Cleavage
Alkyne Hydration
Strong Oxidative Cleavage
Alkynide Multistep Synthesis

Ch. 10 - Conjugation in Alkadienes and Allylic Systems

Introduction to Conjugation
Stability of Conjugated Intermediates
Basics of MO Theory
Drawing Atomic Orbitals
Drawing Molecular Orbitals
FMOT: Finding HOMO/LUMO
Orbital Diagram: 3-atoms- Allylic Ions
Allylic Halogenation
Orbital Diagram: 4-atoms- 1,3-butadiene
Intro to Pericyclic Reactions
Thermal Cycloaddition Reactions
Conjugated Hydrohalogenation
Diels-Alder Reaction

Ch. 11 - Arenes and Aromaticity

Introduction to Aromaticity
Benzene Nomenclature
Birch Reduction
Side-Chain Halogenation
Side-Chain Oxidation
Four Tests of Aromaticity
Counting Pi Electrons
Aromaticity of Hydrocarbons
Aromaticity of Annulenes
Aromaticity of Heterocycles
Inscribed Polygon Method
Acidity of Aromatic Hydrocarbons
Basicity of Aromatic Heterocycles
Ionization of Aromatics

Ch. 12 - Reactions of Aromatic Compounds

EAS: Introduction
EAS: Reactions
EAS: Generating Electrophiles
EDGs and EWGs
EAS: Ortho vs. Para Positions
Limitations of Friedel-Crafts Alkyation
Advantages of Friedel-Crafts Acylation
Wolff-Kischner 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
SNAr Mechanism
Benzyne Pathway

Ch. 13 - Spectroscopy

Purpose of Analytical Techniques
IR Spect: General Features
IR Spect: Frequencies
IR Spect: Drawing Spectra
IR Spect: Extra Practice
1H NMR: General Features
1H NMR: Number of Signals
1H NMR: Chemical Shifts
1H NMR: Spin-Splitting
1H NMR: Integration
1H NMR: Cumulative Practice
13C NMR: General Features
Structure Determination without Mass Spect
Mass Spect: Introduction
Mass Spect: Fragmentation
Mass Spect: Isotopes

Ch. 14 - Organometallic Compounds

Nucleophilic Addition
Preparation of Organometallics
Grignards and Organolithium Reactions
Alcohol Protecting Groups with Organometallics
Organometallic Cumulative Practice
Carbenes and Cyclopropation

Ch. 15 - Alcohol, Diols, and Thiols

Review of Alcohol Synthesis
Intro to Redox
Reduction
Redox Retrosynthesis
Oxidation
Syn Vicinal Dihydroxylation
Epoxide Ring Opening
Fischer Esterification (Simplified)
Thiol and Sulfide Nomenclature
Reactions of Thiols

Ch. 16 - Ethers, Epoxides, and Sulfides

Advanced Alcohol Nomenclature
Ether Nomenclature
Epoxide Nomenclature
Thiol and Sulfide Nomenclature
Making Ethers - Williamson Ether Synthesis
Alcohol Protecting Groups
Cleavage of Ethers
Epoxidation
Epoxide Ring Opening
Sharpless Epoxidation
Oxidation of Sulfides

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

Aldehyde Nomenclature
Ketone Nomenclature
Intro to Redox
Carbonyls Via Oxidation
Ozonolysis to Yield Ketones
Aldehydes Via Reduction
Alkyne Hydration to Yield Ketones
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
The Wittig Reaction
Ketone and Aldehyde Synthesis Reactions

Ch. 18 - Carboxylic Acids

Carboxylic Acid Nomenclature
Carbonation of Grignard Reagents
Fischer Esterification (Simplified)
Decarboxylation

Ch. 19 - Carboxylic Acids Derivatives

Ester Nomenclature
Acid Chloride Nomenclature
Anhydride Nomenclature
Nitrile 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
Lactones, Lactams and Cyclization Reactions
Organometallics on Nitriles

Ch. 20 - Enols and Enolates

Alpha-Carbons and Tautomerization
Enolates
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
Electrophilic Alpha-Halogenations
Condensation Reactions
Aldol Condensation
Directed Condensations
Crossed Aldol Condensation
Claisen-Schmidt Reaction
Claisen Condensation
Intramolecular Condensation
Conjugate Addition (1,2, vs. 1,4 Addition)
Michael Reaction
Robinson Annulation

Ch. 21 - Amines

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

Ch. 22 - Phenols

Acidity of Phenols
Cope Rearrangement
Claisen Rearrangement

Ch. 23 - 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 - Epimerization
Monosaccharides - Aldose-Ketose Rearrangement
Monosaccharides - Acylation
Monosaccharides - O-Glycosides
Monosaccharides - N-Glycosides
Monosaccharides - Reduction (Alditols)
Monosaccharides - Weak Oxidation (Aldonic Acid)
Monosaccharides - Reducing Sugars
Monosaccharides - Strong Oxidation (Aldaric Acid)
Monosaccharides - Oxidative Cleavage
Monosaccharides - Kiliani-Fischer Synthesis
Monosaccharides - Wohl Degradation
Condensation into Disaccharides
Polysaccharides

Carey 8th Edition Solutions

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

Dehydration of 2,2,3,4,4-pentamethyl-3-pentanol gave two alkenes A and B. Ozonolysis of the lower boiling alkene A gave formaldehyde (H2C=O) and 2,2,4,4-tetramethyl-3-pentanone. Ozonolysis of B gave formaldehyde and 3,3,4,4-tetramethyl-2-pentanone. Identify A and B, and suggest an explanation for the formation of B in the dehydration reaction.

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