Reactions of Alcohols

• Nomenclature of Alcohols: Naming Alcohols based on IUPAC Rules with Practice Problems
• Preparation of Alcohols via Substitution or Addition Reactions
• Reaction of Alcohols with HCl, HBr and HI Acids
• Mesylates and Tosylates as Good Leaving Groups
• SOCl₂ and PBr₃ for Conversion of Alcohols to Alkyl Halides
• The Williamson Ether Synthesis
• POCl₃ for Dehydration of AlcoholsAlcohols in Substitution Reactions with Tons of Practice Problems
• Dehydration of Alcohols by E1 and E2 Elimination
• LiAlH4 and NaBH4 Carbonyl Reduction Mechanism
• Alcohols from Carbonyl Reductions – Practice Problems
• Grignard Reaction in Preparing Alcohols with Practice Problems
• Grignard Reaction in Organic Synthesis with Practice Problems
• Protecting Groups For Alcohols and Their Use in Organic Synthesis
• Oxidation of Alcohols: PCC, PDC, CrO3, DMP, Swern and All of That
• NaIO4 Oxidative Cleavage of Diols

Epoxides

• Preparation of Epoxides
• Reactions of Epoxides Practice Problems

Conjugated Systems

• Resonance and Conjugated Dienes
• Allylic Carbocations
• 1,2 and 1,4 Electrophilic Addition to Dienes
• Kinetic vs Thermodynamic Control of Electrophilic Addition to Dienes

The Diels-Alder Reaction

• Diels Alder Reaction: Dienes and Dienophiles
• Predict the Products of the Diels-Alder Reaction with Practice Problems
• Endo and Exo products of Diels-Alder Reaction with Practice Problems
• Regioselectivity of the Diels–Alder Reaction with Practice Problems
• Identify the Diene and Dienophile of the Diels–Alder Reaction with Practice Problems
• Diels Alder Reaction in Organic Synthesis Practice Problems

Aromatic Compounds

• Naming Aromatic Compounds
• Introduction to Aromatic Compounds
• Benzene – Aromatic Structure and Stability
• Aromaticity and Huckel’s Rule
• Identify Aromatic, Antiaromatic, or Nonaromatic Compounds

Electrophilic Aromatic Substitution

• Electrophilic Aromatic Substitution – The Mechanism
• Friedel-Crafts Alkylation with Practice Problems
• Friedel-Crafts Acylation with Practice Problems
• The Alkylation of Benzene by Acylation-Reduction
• Ortho Para Meta Directors in Electrophilic Aromatic Substitution with Practice Problems
• Ortho Para and Meta in Disubstituted Benzenes
• Why Are Halogens Ortho-, Para- Directors yet Deactivators ?
• Limitations on Electrophilic Aromatic Substitution Reactions
• Orientation in Benzene Rings With More Than One Substituent
• Synthesis of Aromatic Compounds From Benzene
• Electrophilic Aromatic Substitution with Arenediazonium Salts
• Reactions at the Benzylic Position
• Nucleophilic Aromatic Substitution

Aldehydes and Ketones

• Nomenclature of Aldehydes and Ketones
• How to Name a Compound with Multiple Functional Groups
• Preparation of Aldehydes and Ketones
• Nucleophilic Addition to Carbonyl Groups
• The Addition-Elimination Mechanism
• Reduction of Carbonyl Compounds by Hydride Ion
• Reactions of Aldehydes and Ketones with Water
• Reactions of Aldehydes and Ketones with Alcohols: Acetals and Hemiacetals
• Acetals as Protecting Groups for Aldehydes and Ketones
• Imines from Aldehydes and Ketones with Primary Amines
• Enamines from Aldehydes and Ketones with Secondary Amines
• Reactions of Aldehydes and Ketones with Amines-Practice Problems
• Acetal Hydrolysis Mechanism
• Imine and Enamine Hydrolysis Mechanism
• The reaction of Aldehydes and Ketones with CN Cyanohydrin Formation
• Hydrolysis of Acetals, Imines and Enamines-Practice Problems
• The Wittig Reaction: Examples and Mechanism
• The Wittig Reaction-Practice Problems

Carboxylic Acids and Their Derivatives-Nucleophilic Acyl Substitution

• Preparation of Carboxylic Acids
• Fischer Esterification
• Ester Hydrolysis by Acid and Base-Catalyzed Hydrolysis
• What is Transesterification?
• Esters Reaction with Amines – The Aminolysis Mechanism
• Ester Reactions Summary and Practice Problems
• Preparation of Acyl (Acid) Chlorides (ROCl)
• Reactions of Acid Chlorides (ROCl) with Nucleophiles
• Reaction of Acyl Chlorides with Grignard and Gilman (Organocuprate) Reagents
• Reduction of Acyl Chlorides by LiAlH4, NaBH4, and LiAl(OtBu)3H
• Preparation and Reaction Mechanism of Carboxylic Anhydrides
• Amides – Structure and Reactivity
• Amides Hydrolysis: Acid and Base-Catalyzed Mechanism
• Amide Dehydration Mechanism by SOCl2, POCl3, and P2O5
• Amide Reduction Mechanism by LiAlH4
• Amides Preparation and Reactions Summary
• Amides from Carboxylic Acids-DCC and EDC Coupling
• The Mechanism of Nitrile Hydrolysis To Carboxylic Acid
• Nitrile Reduction Mechanism with LiAlH4 and DIBAL to Amine or Aldehyde
• The Mechanism of Grignard and Organolithium Reactions with Nitriles
• Carboxylic Acids and Their Derivatives Practice Problems

Alpha Carbon Chemistry: Enols and Enolates

• Alpha Halogenation of Enols and Enolates
• The Haloform and Iodoform Reactions
• Alpha Halogenation of Carboxylic Acids
• Alpha Halogenation of Enols and Enolates Practice Problems
• Aldol Reaction – Principles and Mechanism
• Aldol Condensation – Dehydration of Aldol Addition Product
• Intramolecular Aldol Reactions
• Aldol Addition and Condensation Reactions – Practice Problems
• Crossed Aldol And Directed Aldol Reactions
• Crossed Aldol Condensation Practice Problems
• Alkylation of Enolates Alpha Position
• Enolate Alkylation Practice Problems
• Acetoacetic Ester Synthesis
• Acetoacetic Ester Enolates Practice Problems
• Malonic Ester Synthesis
• Michael Reaction: The Conjugate Addition of Enolates
• Robinson Annulation, Shortcut, and Retrosynthesis
• Claisen Condensation
• Dieckmann condensation – An Intramolecular Claisen Reaction
• Crossed Claisen and Claisen Variation Reactions
• Claisen Condensation Practice Problems
• Stork Enamine Synthesis
• Enolates in Organic Synthesis – a Comprehensive Practice Problem

Amines

• Preparation of Amines
• The Gabriel Synthesis of Primary Amines
• The Hofmann Elimination of Amines and Alkyl Fluorides
• Imines from Aldehydes and Ketones with Primary Amines
• Enamines from Aldehydes and Ketones with Secondary Amines
• The Reaction of Amines with Nitrous Acid
• Reactions of Amines Practice Problems

Organic Synthesis Problems

• Organic Chemistry Multistep Synthesis Practice Problems
• Acetals as Protecting Groups for Aldehydes and Ketones
• How to Choose Molecules for Doing SN2 and SN1 Synthesis-Practice Problems
• Alkene Reactions Practice Problems
• Changing the Position of a Double Bond
• Changing the Position of a Leaving Group
• Alkenes Multi-Step Synthesis Practice Problems
• Alkyne Synthesis Reactions Practice Problems
• Radical Halogenation in Organic Synthesis
• Grignard Reaction in Organic Synthesis with Practice Problems
• Ortho Para Meta Directors in Electrophilic Aromatic Substitution with Practice Problems
• Orientation in Benzene Rings With More Than One Substituent

Carbohydrates

• Carbohydrates – Structure and Classification
• Erythro and Threo
• R and S Configuration on Fischer Projections
• D and L Sugars
• Aldoses and Ketoses: Classification and Stereochemistry
• Epimers and Anomers
• Converting Fischer, Haworth, and Chair forms of Carbohydrates
• Mutarotation
• Glycosides
• Isomerization of Carbohydrates
• Ether and Ester Derivatives of Carbohydrates
• Oxidation of Monosaccharides
• Reduction of Monosaccharides
• Kiliani–Fischer Synthesis
• Wohl Degradation