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9.5 Introduction to Addition Reactions of Alkynes

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Chapter 1 – Electrons, Bonding, and Molecular Properties
- 1.1 Lewis Structures
- 1.2 Formal Charges
- 1.3 Valence Bond Theory and Hybridization
- 1.4 Molecular Orbital Theory
- 1.5 Polarity
- 1.6 Intermolecular Forces
Chapter 2 – Molecular Representations and Resonance
- 2.1 Condensed Structures
- 2.2 Bond Line Structures
- 2.3 Functional Groups
- 2.4 Resonance
Chapter 3 – Acids and Bases
- 3.1 Introduction to Acids and Bases
- 3.2 Ranking Acids and Bases
Chapter 4 – Alkanes
- 4.1 Naming Alkanes
- 4.2 Naming Complex Substituents
- 4.3 Naming Bicyclic Compounds
- 4.4 Drawing Constitutional Isomers
- 4.5 Newman Projections
- 4.6 Cycloalkanes and Cyclohexane Chair Conformations
Chapter 5 – Isomers and Stereochemistry
- 5.1 Overview of Isomerism
- 5.2 Absolute Configurations | How to Assign R and S
- 5.3 Molecules with Multiple Chiral Centers
- 5.4 Fischer Projections
- 5.5 Determining the Relationship Between a Pair of Molecules
- 5.6 Amine Inversion and Chiral Molecules Without Chiral Centers
- 5.7 Optical Activity
Chapter 6 – Organic Reactions and Mechanisms
- 6.1 Reaction Enthalpies and Bond Dissociation Energies
- 6.2 Entropy, Gibbs Free Energy, and the Equilibrium Constant
- 6.3 The Kinetics of Organic Reactions
- 6.4 Nucleophiles, Electrophiles, and Intermediates
- 6.5 Reaction Mechanisms and Curved Arrow Pushing
Chapter 7 – Substitution and Elimination Reactions
- 7.1 SN2 Reactions
- 7.2 SN1 Reactions
- 7.3 SN1 vs SN2
- 7.4 Introduction to Elimination Reactions [Zaitsev’s Rule and the Stability of Alkenes]
- 7.5 E2 Reactions
- 7.6 E1 Reactions and E1 vs E2
- 7.7 Distinguishing Between SN1/SN2/E1/E2
Chapter 8 – Alkenes
- 8.0 Naming Alkenes
- 8.1 Introduction to Alkene Addition Reactions
- 8.2 Hydrohalogenation
- 8.3 Hydration of Alkenes
- 8.4 Addition of Alcohols
- 8.5 Catalytic Hydrogenation
- 8.6 Halogenation of Alkenes and Halohydrin Formation
- 8.7 Epoxidation, Anti Dihydroxylation, and Syn Dihydroxylation
- 8.8 Predicting the Products of Alkene Addition Reactions
- 8.9 Oxidative Cleavage Ozonolysis and Permanganate Cleavage
Chapter 9 – Alkynes
- 9.1 Naming Alkynes
- 9.2 Acidity of Alkynes
- 9.3 Synthesis of Alkynes
- 9.4 Reduction of Alkynes
- 9.5 Hydrohalogenation of Alkynes
- 9.6 Halogenation of Alkynes
- 9.7 Hydration of Alkynes
- 9.8 Ozonolysis of Alkynes
- 9.9 Alkylation of Acetylide Ions
Chapter 10 – Radical Reactions
- 10.1 Free Radical Halogenation
- 10.2 The Free Radical Halogenation Mechanism
- 10.3 Allylic and Benzylic Bromination with NBS
- 10.4 Addition of HBr and Peroxide
Chapter 11 – Synthesis
- 11.1 Introduction to Organic Synthesis
- 11.2 Common Patterns in Organic Synthesis (Involving Alkenes)
- 11.3 Common Patterns in Organic Synthesis (involving Alkynes)
Chapter 12 – Alcohols
- 12.1 Properties and Nomenclature of Alcohols
- 12.2 Acidity of Alcohols and Phenols
- 12.3a Synthesis of Alcohols; Reduction of Ketones and Aldehydes
- 12.3b Synthesis of Alcohols; Grignard Addition
- 12.4 Protecting Alcohols
- 12.5a Reaction with HCl, HBr, and HI
- 12.5b Substitution with PBr3 and SOCl2
- 12.5c Formation of Tosylate Esters
- 12.6 Elimination Dehydration
- 12.7 Oxidation with Chromic Acid and PCC
Chapter 13 – Ethers, Epoxides, Thiols, and Sulfides
- 13.1 Introduction to Nomenclature of Ethers
- 13.2 Crown Ethers
- 13.3 Synthesis and Reactions of Ethers
- 13.4 Nomenclature of Epoxides
- 13.5 Synthesis of Epoxides
- 13.6 Ring Opening of Epoxides
- 13.7 Nomenclature, Synthesis, and Reactions of Thiols
- 13.8 Nomenclature, Synthesis, and Reactions of Sulfides
Chapter 14 – IR Spectroscopy and Mass Spectrometry
- 14.1 Introduction to IR Spectroscopy
- 14.2a IR Spectra of Carbonyl Compounds
- 14.2b The Effect of Conjugation on the Carbonyl Stretching Frequency
- 14.3 Interpreting More IR Spectra
- 14.4 Introduction to Mass Spectrometry
- 14.5 Isotope Effects in Mass Spectrometry
- 14.6a Fragmentation Patterns of Alkanes, Alkenes, and Aromatic Compounds
- 14.6b Fragmentation Patterns of Alkyl Halides, Alcohols, and Amines
- 14.6c Fragmentation Patterns of Ketones and Aldehydes
Chapter 15 – NMR Spectroscopy
- 15.1 Introduction to NMR
- 15.2 The Number of Signals in C 13 NMR
- 15.3 The Number of Signals in Proton NMR
- 15.4 Homotopic vs Enantiotopic vs Diastereotopic
- 15.5a The Chemical Shift in C 13 and Proton NMR
- 15.5b The Integration or Area Under a Signal in Proton NMR
- 15.5c The Splitting or Multiplicity in Proton NMR
- 15.6a Interpreting NMR Example 1
- 15.6b Interpreting NMR Example 2
- 15.6c Interpreting NMR Example 3
- 15.6d Structural Determination From All Spectra Example 4
- 15.6e Structural Determination From All Spectra Example 5
- 15.7 Complex Splitting
Chapter 16 – Conjugated Pi Systems
- 16.1 Introduction to Conjugated Systems and Heats of Hydrogenation
- 16.2a Introduction to Pi Molecular Orbitals Ethylene
- 16.2b Pi Molecular Orbitals 1,3 Butadiene
- 16.2c Pi Molecular Orbitals the Allyl System
- 16.2d Pi Molecular Orbitals 1,3,5 Hexatriene
- 16.3 UV Vis Spectroscopy
- 16.4 Addition Reactions to Conjugated Dienes
- 16.5a Introduction to Diels Alder Reactions
- 16.5b Stereoselectivity and Regioselectivity in Diels Alder Reactions
- 16.5c Diels Alder Reactions with Cyclic Dienes
- 16.5d Conservation of Orbital Symmetry in Diels Alder Reactions
- 16.6 Cycloaddition Reactions
- 16.7 Electrocyclic Reactions
- 16.8 Sigmatropic Rearrangements
Chapter 17 – Aromatic Compounds
- 17.1 Nomenclature of Benzenes
- 17.2a Criteria for Aromatic Compounds
- 17.2b Aromatic vs Nonaromatic vs Antiaromatic
- 17.3 The Effects of Aromaticity on SN1 Reactions and Acidity Basicity
- 17.4 Aromaticity and Molecular Orbital Theory
Chapter 18 – Reactions of Aromatic Compounds
- 18.1 Introduction to Aromatic Substitution Reactions
- 18.2a EAS Bromination and Chlorination
- 18.2b EAS Sulfonation and Desulfonation
- 18.2c EAS Nitration
- 18.2d EAS Friedel Crafts Alkylation and Acylation
- 18.2e EAS Activating and Deactivating Groups and Ortho Para and Meta Directors
- 18.2f EAS Predicting the Products of EAS Reactions
- 18.3 Catalytic Hydrogenation and the Birch Reduction
- 18.4a Side Chain Oxidation with Permanganate or Chromic Acid
- 18.4b Benzylic Bromination with NBS
- 18.4c The Clemmensen and Wolff Kishner Reductions
- 18.4d Side Chain General Reduction
- 18.5 Nucleophilic Aromatic Substitution
Chapter 19 – Ketones and Aldehydes
- 19.1 Nomenclature of Ketones and Aldehydes
- 19.2 Synthesis of Ketones and Aldehydes
- 19.3 Introduction to Nucleophilic Addition Reactions
- 19.4 Hydration Addition of Water
- 19.5a Addition of Alcohols
- 19.5b Cyclic Acetals as Protecting Groups
- 19.6a Addition of Primary Amines Imine Formation
- 19.6b Addition of Secondary Amines Enamine Formation
- 19.6c Mechanism for the Wolff Kishner Reduction
- 19.7 Reduction via Thioacetals
- 19.8 Hydride Reduction Reactions
- 19.9a Addition of Acetylide Ions and Grignard Reagents
- 19.9b Addition of HCN Cyanohydrin Formation
- 19.9c The Wittig Reaction
- 19.10 Baeyer Villiger Oxidation
Chapter 20 – Carboxylic Acids and Acid Derivatives
- 20.1 Introduction to and Physical Properties of Carboyxylic Acids and Acid Derivatives
- 20.2a Nomenclature of Carboxylic Acids
- 20.2b Nomenclature of Acid Halides
- 20.2c Nomenclature of Acid Anhydrides
- 20.2d Nomenclature of Esters
- 20.2e Nomenclature of Amides
- 20.2f Nomenclature of Nitriles
- 20.3 Introduction to Nucleophilic Acyl Substitution
- 20.4 Reaction with Organometallic Reagents
- 20.5 Hydride Reduction
- 20.6 Interconversion of Carboxylic Acids and Derivatives
- 20.7 The Mechanisms of Nucleophilic Acyl Substitution
- 20.8a Synthesis of Acid Halides
- 20.8b Reactions of Acid Halides
- 20.9 Synthesis and Reactions of Acid Anhydrides
- 20.10a Synthesis of Esters
- 20.10b Reactions of Esters
- 20.11 Synthesis and Reactions of Carboxylic Acids
- 20.12 Synthesis and Reactions of Amides
- 20.13 Synthesis and Reactions of Nitriles
Chapter 21 – Substitution Reactions at the Alpha Carbon
- 21.1 Acidity of the Alpha Hydrogen
- 21.2 General Mechanisms of Alpha Substitution Reactions
- 21.3a Alpha Halogenation
- 21.3b The Haloform Reaction
- 21.3b The HVZ Reaction
- 21.4a Alpha Alkylation
- 21.4b The Stork Synthesis
- 21.5a Introduction to Aldol Reactions
- 21.5b Mechanisms of Aldol Reactions
- 21.5c Mixed Aldol Reactions
- 21.5d Intramolecular Aldol Reactions
- 21.6a Claisen Condensation Reactions
- 21.6b Dieckmann Condensation Reactions
- 21.7a Beta Decarboxylation
- 21.7b The Malonic Ester Synthesis
- 21.7c The Acetoacetic Ester Synthesis
- 21.8 Michael Reactions
- 21.9 The Robinson Annulation
Chapter 22 – Amines
- 22.1 Classification of Amines
- 22.2 Nomenclature of Amines
- 22.3 Basicity of Amines
- 22.4a Synthesis of Amines Reduction
- 22.4b Synthesis of Amines Hofmann Rearrangement
- 22.4c Synthesis of Amines Curtius Rearrangement and Schmidt Reaction
- 22.4d Synthesis of Amines Gabriel Synthesis
- 22.4e Synthesis of Amines Reductive Amination
- 22.5 Acylation
- 22.6 Hofmann Elimination
- 22.7 Cope Elimination
- 22.8a Reaction with Nitrous Acid and the Sandmeyer Reactions
- 22.8b Azo Coupling
- 22.9 EAS Reactions with Nitrogen Heterocycles

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