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Organic Chemistry Topics that we cover

Ch. 1 - A Review of General Chemistry

Intro to Organic Chemistry
Atomic Structure
Wave Function
Molecular Orbitals
Sigma and Pi Bonds
Octet Rule
Bonding Preferences
Formal Charges
Skeletal Structure
Drawing Correct Bondline Structures
Lewis Structure
Condensed Structural Formula
Empirical Formulas
Degrees of Unsaturation
Isomer
Constitutional Isomers
Intro to Stereoisomers
How to Recognize Cis and Trans Isomers
Drawing Isomers
Resonance Structures
Resonance of Radicals
Resonance Hybrids
Major and Minor Resonance Contributors
Hybridization
Molecular Geometry
Molecular Geometry with Resonance
3D Hybrid Orbital Drawings
The CHM 7
Electronegativity
Polar Vs. Nonpolar
Covalent Bond
Polar Bond
Cumulative General Concepts

Ch. 2 - Molecular Representations

Intermolecular Forces
London Dispersion Force
Van Der Waals
How To Determine Solubility
Hydrophilicity
Functional Groups
Carbonyl
Amine
Amide
Drawing Isomers with Functional Groups

Ch. 3 - Acids and Bases

Organic Chemistry Reactions
Reaction Mechanism
Predicting Chemical Reactivity
Nucleophiles and Electrophiles
Acids and Bases
Acid and Base Conjugates
Give the conjugate acid for each compound below
Equilibrium Constant
Calculating Equilibrium Constants Using pKa
pKa
Acid Base Equilibrium
Ranking Acidity
Element Effect
Resonance Effect
Inductive Effect
Hybridization Effect
Steric Effects
Acid and Base Equilibrium with ARIO
Predicting Protonation Sites
Lewis Acids and Bases
Lewis Acid-Base Reactions
Acid and Base Synthesis

Ch. 4 - Alkanes and Cycloalkanes

IUPAC Naming
Alkyl Groups
Complex Substituent Nomenclature
Alkyl
t-Butyl, sec-Butyl, isobutyl, n-butyl
Naming Cycloalkanes
Naming Bicyclic Compounds
Spiro Bicyclic Nomenclature
Advanced Bicyclic Nomenclature
Naming Alkyl Halides
Naming Alkenes
Alkene Nomenclature
Alkyne Nomenclature
Alkyne Substituent Common Nomenclature
Naming Alcohols
Naming Amines
Cis and Trans Nomenclature
Cis vs Trans
Conformational Isomers
Newman Projections
Drawing Newman Projections
Dihedral Angle
Barrier To Rotation
Newman Projections to Bondline Structures
Newman Projections Explain s-trans Hydrocarbon Bonds
Newman Projections of Rings
Ring Strain
Axial vs Equatorial
Cis vs Trans Conformations
Equatorial Preference
Chair Flip
Calculating Energy Difference Between Chair Conformations
A-Values
Cyclohexane - Newman Projections
Decalin
Catalytic Hydrogenation of Alkenes
Alkane Combustion

Ch. 5 - Chirality

Constitutional Isomers vs. Stereoisomers
Chirality
Test 1: Plane of Symmetry
Test 2: Stereocenter Test
R and S Configuration
Enantiomers vs. Diastereomers
Predicting Chirality
Determining Total Number of Stereoisomers
Atropisomers
Meso Compound
Test 3: Disubstituted Cycloalkanes
What is the Relationship Between Isomers?
Fischer Projection
R and S of Fischer Projections
R and S of Newman Projections
Racemic Mixture
Optical Activity
Enantiomeric Excess
Calculations with Enantiomeric Percentages
Non-Carbon Chiral Centers
Cumulative Chirality Questions
Prochirality
Enantiomeric Separation by Diastereoisomeric Salts
Enantiomeric Separation by Enzymes
Enantiomeric Separation by Chiral Chromatography
Achiral

Ch. 6 - Thermodynamics and Kinetics

Energy Diagram
Gibbs Free Energy
Enthalpy
Entropy
Chemical Equilibrium
Kinetics
Hammond Postulate
Hyperconjugation
Carbocation Stability
Rank the following carbocations in order of decreasing stability
Carbocation Intermediate Rearrangements
Carbanion Stability

Ch. 7 - Substitution Reactions

Alkyl Halide
Nucleophilic Substitution
Good Leaving Groups
Physical Properties of RX
SN2 Reaction
SN1 reaction
Ion Pairing Effects
Substitution Comparison

Ch. 8 - Elimination Reactions

E2 Mechanism
Beta Hydrogen
E2 - Anti-Coplanar Requirement
E2 - Anti-Coplanar Requiring Rotation
E2 - Cumulative Practice
E1 Reaction
Solvents
Leaving Groups
Nucleophiles and Basicity
Rate Calculations
Rate Calculations of Competitive Mechanisms
SN1 SN2 E1 E2 Chart (Big Daddy Flowchart)
Cumulative Substitution/Elimination
Substitution/Elimination Retrosynthesis
Intramolecular Substitution/Elimination Practice
The E1cb Mechanism

Ch. 9 - Alkenes and Alkynes

Alkene Stability
Zaitsev Rule
Dehydrohalogenation
Hofmann Elimination of Alkyl Fluorides
Debromination
Double Elimination
Acetylide
Isomerization of Alkynes
Hydrogenation of Alkynes
Dissolving Metal Reduction Mechanism
Hydrogenation Retrosynthesis
Dehydration Reaction
POCl3 Dehydration
Alkynide Synthesis
Alkynide Retrosynthesis
Bredt's Rule

Ch. 10 - Addition Reactions

Addition Reaction
Thermodynamics of Addition-Elimination Equilibria
Markovnikov
Stereospecificity vs. Stereoselectivity
Hydrohalogenation
Sulfonation
Acid-Catalyzed Hydration
Oxymercuration
Oxymercuration-Reduction Full Mechanism
Hydroboration
Hydroboration-Oxidation Full Mechanism
Alkoxymercuation
Hydrogenation
Halogenation
Interhalogenation
Halohydrin
Haloether Formation
Carbene
Simmons-Smith Addition Mechanism
Epoxidation
Epoxide Reactions
Regiospecificity of Acid-Catalyzed Ring Openings
Anti Vicinal Dihydroxylation
Dihydroxylation
Ozonolysis
Ozonolysis Full Mechanism
Ozonolysis Retrosynthesis
Oxidative Cleavage
Alkyne Oxidative Cleavage
Alkyne Hydrohalogenation
Alkyne Halogenation
LiBr and Acetic Acid for Anti Vinyl Dihaldes
Alkyne Hydration
Alkyne Hydroboration
Addition Reagent Facts
Predicting Stereoisomers of Addition Reactions
Addition Missing Reagent
Addition Synthesis
Addition Texas Two-Step
Addition Multi Step
Addition Retrosynthesis
Addition to Concave vs. Convex Rings

Ch. 11 - Radical Reactions

Radical Reaction
Radical Stability
Free Radical Halogenation
Radical Selectivity
Isomers of Radical Halogenation
Calculating Radical Yields
Anti Markovnikov Addition of Br
Radical Hydrohalogenation of Alkynes
Free Radical Polymerization
Allylic Bromination
Alkyl Halide Radical Reduction
Ether Autooxidation
Cyclopropane as a Nucleophile
Radical Disproportionation
Radical Texas Two-Step
Radical Synthesis
Radical Retrosynthesis

Ch. 12 - Alcohols, Ethers, Epoxides and Thiols

Hydroxyl Group
Acidity/Basicity of Alcohols
Active Metals as bases on Alcohols
Alcohol Nomenclature
Naming Ethers
Crown Ether Nomenclature
Cyclic Ether Nomenclature
Naming Epoxides
Naming Thiols
Alcohol Synthesis
Leaving Group Conversions - Using HX
Leaving Group Conversions - SOCl2 and PBr3
Leaving Group Conversions - Sulfonyl Chlorides
Leaving Group Conversions Retrosynthesis
Leaving Group Conversions Summary
Physical Properties of Ethers
Williamson Ether Synthesis
Making Ethers - Alkoxymercuration
Making Ethers - Alcohol Condensation
Making Ethers - Acid-Catalyzed Alkoxylation
Making Ethers - Cumulative Practice
Williamson Ether Retrosynthesis
Synthesis of Phenol Ethers
Ether Cleavage
Cleavage of Phenyl Ethers
Alcohol Protecting Groups
t-Butyl Ether Protecting Groups
Silyl Ether Protecting Groups
Sharpless Epoxidation
Acidity of Thiols
Thiol Reactions
Sulfide Oxidation
Disulfide Reduction

Ch. 13 - Alcohols and Carbonyl Compounds

Oxidizing and Reducing Agents
Calculating Oxidation States
Oxidizing Agent
Swern Oxidation
Dess–Martin Periodinane (DMP) Oxidation
Reducing Agent
Reduction Mechanisms
LiAlH4
Redox Retrosynthesis
Oxidation with Bleach (HOCl)
Glycol Cleavage (Periodic Acid - HIO4)
Ketone and Aldehyde Hydroboration
Alcohol Reduction
Reduction of Epoxides with LAH
Nucleophilic Addition
Preparation of Organometallics
Grignard Reaction
Gilman Reactions
Organometallic Synthesis
Organometallic Retrosynthesis
Protecting Alcohols from Organometallics
Organometallic Cumulative Practice
Organometallic Roadmaps

Ch. 14 - Synthetic Techniques

Synthetic Cheatsheet
Moving Functionality
Alkynide Alkylation
Alkane Halogenation
Retrosynthesis

Ch. 15 - Analytical Techniques: IR, NMR, Mass Spect

Purpose of Analytical Techniques
Infrared Spectroscopy
Infrared Spectroscopy Table
IR Spect: Frequencies Considering Solution Effects
IR Spect: Drawing Spectra
IR Spect: Extra Practice
IR Spect: Structure Determination
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
1H NMR: Proton Exchange
1H NMR: Fast Proton Exchange (D2O)
NMR Practice
Carbon NMR
13C NMR: Cumulative Practice
2D NMR - COSY
Structure Determination without Mass Spect
Mass Spectrometry
Mass Spect: Fragmentation
Mass Spect: McLafferty Rearrangement
Mass Spect: Isotopes
Structure Determination with Mass Spect

Ch. 16 - Conjugated Systems

Diene
Conjugation Chemistry
Stability of Conjugated Intermediates
Allylic Halogenation
Conjugated Hydrohalogenation (1,2 vs 1,4 addition)
Conjugated Halogenation
Diels-Alder Reaction
Diels-Alder Inductive Effects
Diels-Alder Forming Bridged Products
Diels-Alder Regiospecficity
Diels-Alder Asymmetric Induction
Diels-Alder Synthesis
Diels-Alder Retrosynthesis
Molecular Orbital Theory
Drawing Atomic Orbitals
Drawing Molecular Orbitals
HOMO LUMO
Orbital Diagram: 3-atoms- Allylic Ions
Allylic SN1 and SN2
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
Cumulative Orbital Diagram Problems
Pericyclic Reaction
Thermal Cycloaddition Reactions
Photochemical Cycloaddition Reactions
Cumulative Cycloaddition Reactions
Thermal Electrocyclic Reactions
Photochemical Electrocyclic Reactions
Cumulative Electrocyclic Problems
Sigmatropic Rearrangement
Cumulative Sigmatropic Problems
Cope Rearrangement
Claisen Rearrangement
UV-Vis Spect Basics
UV-Vis Spect Beer's Law
Molecular Electronic Transition Therory
Woodward-Fieser Rules

Ch. 17 - Aromaticity

Aromaticity
Physical Properties of Arenes
Resonance Model of Benzene
Huckel's Rule
Pi Electrons
Aromatic Hydrocarbons
Annulene
Aromatic Heterocycles
Cumulative Aromaticity Problems
Frost Circle
Naming Benzene Rings
Polycyclic Aromatic Hydrocarbon Nomenclature
Acidity of Aromatic Hydrocarbons
Basicity of Aromatic Heterocycles
Ionization of Aromatics

Ch. 18 - Reactions of Aromatics: EAS and Beyond

Electrophilic Aromatic Substitution
Benzene Reactions
EAS: Halogenation Mechanism
EAS: Nitration Mechanism
EAS: Sulfonation Mechanism
EAS: Friedel-Crafts Alkylation Mechanism
EAS: Friedel-Crafts Acylation Mechanism
EAS: Gatterman–Koch Reaction
EAS: Any Carbocation Mechanism
EAS: Total Benzene Isomers
EAS: Polycyclic Aromatic Hydrocarbons
Electron Withdrawing Groups
EAS: Directing Effects
Resonance Theory of EAS Directing Effects
EAS: Badass Activity Chart
EAS: Ortho vs. Para Positions
Activated Benzene and Polysubstitutions
Acylation of Aniline
Limitations of Friedel-Crafts Alkyation
Advantages of Friedel-Crafts Acylation
Clemmensen Reduction
Blocking Groups - Sulfonic Acid
EAS: Synergistic and Competitive Groups
EAS: Dueling Benzenes
Side-Chain Halogenation
Side-Chain Oxidation
Hydrogenation of Benzene
Birch Reduction
EAS: Sequence Groups
EAS: Missing Reagent
EAS: Synthesis
EAS: Retrosynthesis
Diazonization of Aniline
Diazo Replacement Reactions
Diazo Coupling Reactions
Diazo Sequence Groups
Diazo Retrosynthesis
Nucleophilic Aromatic Substitution
Benzyne
SNAr vs. Benzyne
Aromatic Missing Reagent
Aromatic Synthesis
Aromatic Retrosynthesis
EAS on 5-membered Heterocycles

Ch. 19 - Aldehydes and Ketones: Nucleophilic Addition

Physical Properties of Ketones and Aldehydes
Naming Aldehydes
Naming Ketones
Multi-Functionalized Carbonyl Nomenclauture
Oxidizing and Reducing Agents
Oxidation of Alcohols
Ozonolysis
Catalytic Reduction of Carbonyls
DIBAL
Tollens’s Test
Fehling’s Test 
Alkyne Hydration
Alkyne Hydroboration to Yield Aldehydes
Nucleophilic Addition
Nucleophilic Addition Reactivity
Cyanohydrin
Strecker Synthesis
Organometallics on Ketones
Overview of Nucleophilic Addition of Solvents
Hydrates
Hemiacetal
Acetal
Acetal and Hemiacetal
Acetal Protecting Group
Synthesis Involving Acetals
Thioacetal
Imine vs Enamine
Addition of Amine Derivatives
Wolff Kishner Reduction
Reduction of Carbonyls to Alkanes
Clemmensen vs Wolff-Kischner
Baeyer-Villiger Oxidation
Baeyer-Villiger Oxidation Synthesis
Acid Chloride to Ketone
Weinreb Ketone Synthesis
Nitrile to Ketone
Wittig Reaction
Wittig Retrosynthesis
Horner–Wadsworth–Emmons Reaction
Ketone and Aldehyde Synthesis Reactions
Carbonyl Missing Reagent
Carbonyl Hydrolysis
Carbonyl Synthesis
Carbonyl Retrosynthesis
Reactions of Ketenes
Ketene Synthesis

Ch. 20 - Carboxylic Acid Derivatives: NAS

Carboxylic Acid
Carboxylic Acid Derivatives
Nucleophilic Acyl Substitution Mechanism
Nucleophilic Acyl Substitution Reactivity
Acidity of Carboxylic Acids
Chemoselective Carboxylic Acid Reduction
Naming Carboxylic Acids
Diacid Nomenclature
Ester
Naming Esters
Naming Nitriles
Acid Chloride Nomenclature
Naming Anhydrides
Naming Amides
Carboxylic Acid Derivative Nomenclature
Multi-Functionalized COOH Nomenclauture
Nucleophilic Acyl Substitution
Carboxylic Acid to Acid Chloride
DCC Coupling Agent to Promote Amide Formation
Dehydration of Amide
Hydrolysis of Nitrile
Esters via SN2 Reactions
Methyl Esters Via Diazomethane
Fischer Esterification
Acid-Catalyzed Ester Hydrolysis
Saponification
Transesterification
Lactones, Lactams and Cyclization Reactions
Organometallics on Esters
Organometallics on Carboxylates
Carboxylation
Decarboxylation Mechanism
Carboxylic Acid Missing Reagent
Carboxylic Acid Synthesis
Carboxylic Acid Retrosynthesis

Ch. 21 - Enolate Chemistry: Reactions at the Alpha-Carbon

Tautomerization
Tautomers of Dicarbonyl Compounds
Tautomers of Heteroatomic Compounds
Enolate
Alpha-Carbon Racemization
Acid-Catalyzed Alpha-Halogentation
Base-Catalyzed Alpha-Halogentation
Haloform Reaction
Hell-Volhard-Zelinski Reaction
Amino-Acids via HVZ
Overview of Alpha-Alkylations and Acylations
Enolate Alkylation and Acylation
Enolate Alkylation Synthesis
Carboxylate Alkylation
Enamine Alkylation and Acylation
Enamine Retrosynthesis
Beta-Dicarbonyl Synthesis Pathway
Acetoacetic Ester Synthesis
Malonic Ester Synthesis
Beta-Dicarbonyl Retrosynthesis
Activated Methylenes
Alpha-Carbon Texas Two-Step
Alpha-Carbon Cumulative Retrosynthesis
Dithianes

Ch. 22 - Condensation Chemistry

Condensation Reactions
Aldol Condensation
Directed Condensations
Crossed Aldol Condensation
Claisen-Schmidt Condensation
Aldol Retrosynthesis
Claisen Condensation
Claisen Retrosynthesis
Intramolecular Aldol Condensation
Intramolecular Condensation Retrosynthesis
Knoevenagel Reaction
Mixed Condensations
Conjugate Addition
Michael Addition
Acid-Catalyzed Michael Reaction
Michael Addition Retrosynthesis
Alpha and Beta Alkylation
Robinson Annulation
Robinson Annulation Retrosynthesis
Mannich Reaction
Cannizzaro Reaction
Hydrolysis
Condensation Texas Two-Step
Cumulative Condensation Reactions

Ch. 23 - Amines

Physical Properties of Amines
Chirality of Amines
Amine Basicity
Amine Acidity
Amine Alkylation
Gabriel Synthesis
Amines by Reduction
Nitrogenous Nucleophiles
Reductive Amination
Curtius Rearrangement
Hofmann Rearrangement
Isocyanate Reactions
Hofmann Elimination
Cope Elimination
Nitrosation of Secondary Amines
Amine Synthesis
Amine Retrosynthesis

Ch. 24 - Carbohydrates

Monosaccharide
Monosaccharides - D and L Isomerism
R and S of Sugars
Monosaccharides - Drawing Fischer Projections
Monosaccharides - Erythro and Threo Isomerism
Monosaccharides - Common Structures
Monosaccharides - Common Ketoses
Monosaccharides - Forming Cyclic Hemiacetals
Monosaccharides - Cyclization
Monosaccharides - Pyranose-Furanose Isomerization
Monosaccharides - Haworth Projections
Mutarotation
Epimerization
Monosaccharides - Aldose-Ketose Rearrangement
Monosaccharides - Overview of Reactions
Monosaccharides - Alkylation
Monosaccharides - Acylation
Monosaccharides - Cyclic Acetals
Glycoside
Monosaccharides - O-Glycoside Hydrolysis
Monosaccharides - N-Glycosides
Monosaccharides - Reduction (Alditols)
Monosaccharides - Weak Oxidation (Aldonic Acid)
Reducing Sugars
Monosaccharides - Strong Oxidation (Aldaric Acid)
Monosaccharides - Oxidative Cleavage
Monosaccharides - Osazones
Monosaccharides - Kiliani-Fischer
Monosaccharides - Wohl Degradation
Monosaccharides - Ruff Degradation
Disaccharide
Polysaccharide

Ch. 25 - Phenols

Phenol Nomenclature
Phenol Acidity

Ch. 26 - Amino Acids, Peptides, and Proteins

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

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Brown
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Latest Organic Chemistry Questions

please answer this question with the mechanism.
@aditig5 • about 6 hours ago • Organic Chemistry
Write the structure of the major organic products of the following reactions in the zig-zag form (respect bond angles). Draw all bonds except C-H bonds, all lone pairs and all formal charges (where necessary). Do not use 'C' to label the carbons. Do not consider rearrangements. Identify each reaction as SN1, SN2, or neither and write your answers in the dashed boxes.
@alissak4 • about 21 hours ago • Organic Chemistry → Leaving Group Conversions - Using HX
Identify the rate law for the following reaction
@alicek12 • 1 day ago • Organic Chemistry → Rate Calculations
Identify the be most water-soluble alcohol.
@alicek12 • 1 day ago • Organic Chemistry → Solubility of Alcohols
Identify the major organic product in the following reaction
@alicek12 • 1 day ago • Organic Chemistry → Substitution Comparison
Identify the major organic product in the following reaction
@alicek12 • 1 day ago • Organic Chemistry
Write the structure of the major organic products of the following reactions in the zig-zag form (respect bond angles). Draw all bonds except C-H bonds, all lone pairs and all formal charges (where necessary). Do not use 'C' to label the carbons. Do not consider rearrangements. Identify each reaction as SN1, SN2, or neither and write your answers in the dashed boxes.
@alicek12 • 1 day ago • Organic Chemistry → Cumulative Substitution/Elimination
Write the structure of the major organic products of the following reactions in the zig-zag form (respect bond angles). Draw all bonds except C-H bonds, all lone pairs and all formal charges (where necessary). Do not use 'C' to label the carbons. Do not consider rearrangements. Identify each reaction as SN1, SN2, or neither and write your answers in the dashed boxes.
Write the structure of the major organic products of the following reactions in the zig-zag form (respect bond angles). Draw all bonds except C-H bonds, all lone pairs and all formal charges (where necessary). Do not use 'C' to label the carbons. Do not consider rearrangements. Identify each reaction as SN1, SN2, or neither and write your answers in the dashed boxes. solve (b) please help me
Write the structure of the major organic products of the following reactions in the zig-zag form (respect bond angles). Draw all bonds except C-H bonds, all lone pairs and all formal charges (where necessary). Do not use 'C' to label the carbons. Do not consider rearrangements. Identify each reaction as E1 or E2 and write your answers in the dashed boxes.
@alicek12 • 1 day ago • Organic Chemistry → E2 - Cumulative Practice

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Popular Organic Chemistry Practice Problems

Draw 2-methylpentanoic acid. Include all the hydrogen atoms in your structural formula.

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Consider the following pair of reactions. Predict the type of substitution mechanism, predict which reaction of the pair will occur at the faster rate, and draw the correct organic product.

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Consider the following pair of reactions. Predict the type of substitution mechanism, predict which reaction of the pair will occur at the faster rate, and draw the correct organic product.

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Draw the structure of the cycloalkane 1,4-dimethylcyclohexane. Include hydrogen atoms.

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Label the highlighted functional groups in this molecule.

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