11.3 Decreasing the Length of the Carbon Chain or Opening a Ring

Chad's Organic Chemistry Videos

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 Isomeric Relationships Between 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 – Organic Synthesis (Retrosynthesis)
- 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 Naming Alcohols
- 12.2 Properties of Alcohols
- 12.3 Synthesis of Alcohols
- 12.4 Grignard Reagents
- 12.5 Protecting Alcohols
- 12.6 Substitution Reactions of Alcohols
- 12.7 Elimination Reactions (Dehydration) of Alcohols
- 12.8 Oxidation of Alcohols
- 12.9 Organic Synthesis with Alcohols
Chapter 13 – Ethers, Epoxides, Thiols, and Sulfides
- 13.1 Naming Ethers
- 13.2 Synthesis of Ethers
- 13.3 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
- 13.9 Organic Synthesis with Ethers and Epoxides
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 Pi Molecular Orbitals 1,3 Butadiene
- 16.2b Pi Molecular Orbitals the Allyl System
- 16.2c Pi Molecular Orbitals 1,3,5 Hexatriene
- 16.3 UV Vis Spectroscopy
- 16.4 Electrophilic Addition to Conjugated Dienes
- 16.5 Diels Alder Reactions
- 16.6 Cycloaddition Reactions
- 16.7 Electrocyclic Reactions
- 16.8 Sigmatropic Rearrangements
Chapter 17 – Aromatic Compounds
- 17.1 Naming Benzenes
- 17.2 Aromatic vs Nonaromatic vs Antiaromatic
- 17.3 The Effects of Aromaticity on Reactivity
- 17.4 Pi Molecular Orbitals of Benzene
Chapter 18 – Reactions of Aromatic Compounds
- 18.1 Electrophilic Aromatic Substitution
- 18.2 Friedel Crafts Alkylation and Acylation
- 18.3 Activating and Deactivating Groups | Ortho/Para vs Meta Directors
- 18.4 Catalytic Hydrogenation and the Birch Reduction
- 18.5 Side-Chain Reactions of Benzenes
- 18.6 Nucleophilic Aromatic Substitution
- 18.7 Retrosynthesis with Aromatic Compounds
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 of Ketones and Aldehydes
- 19.4a Formation of Hemiacetals and Acetals (Addition of Alcohols)
- 19.4b Cyclic Acetals as Protecting Groups
- 19.5 Formation of Imines and Enamines (Addition of Amines)
- 19.6 Reduction of Aldehydes and Ketones
- 19.7a Addition of Carbon Nucleophiles (Acetylide Ions, Grignard Reagents,etc.)
- 19.7b The Wittig Reaction
- 19.8 Baeyer Villiger Oxidation
- 19.9 Retrosynthesis with Aldehydes and Ketones
Chapter 20 – Carboxylic Acids and Acid Derivatives
- 20.1 Naming Carboxylic Acids and Carboxylic Acid Derivatives
- 20.2 Nucleophilic Acyl Substitution
- 20.3 The Mechanisms of Nucleophilic Acyl Substitution
- 20.4 Reaction with Organometallic Reagents
- 20.5 Hydride Reduction Reactions
- 20.6 Synthesis and Reactions of Acid Halides
- 20.7 Synthesis and Reactions of Acid Anhydrides
- 20.8 Synthesis and Reactions of Esters
- 20.9 Properties, Synthesis, and Reactions of Carboxylic Acids
- 20.10 Synthesis and Reactions of Amides
- 20.11 Synthesis and Reactions of Nitriles
- 20.12 Retrosynthesis with Carboxylic Acids / Acid Derivatives
Chapter 21 – Substitution Reactions at the Alpha Carbon
- 21.1 Acidity of the Alpha Hydrogen
- 21.2 Mechanisms of Alpha Substitution Reactions
- 21.3 Alpha Halogenation
- 21.4 Alpha Alkylation (including the Stork Reaction)
- 21.5 Aldol Reactions
- 21.6 Claisen Condensation Reactions
- 21.7 The Malonic Ester Synthesis and the Acetoacetic Ester Synthesis
- 21.8 Michael Reactions
- 21.9 The Robinson Annulation
- 21.10 Retrosynthesis with Enolates and Enols
Chapter 22 – Amines
- 22.1 Naming Amines
- 22.2 Basicity of Amines
- 22.3 Synthesis of Amines
- 22.4 Hofmann Elimination and Cope Elimination
- 22.5 Sandmeyer Reactions
- 22.6 EAS Reactions with Nitrogen Heterocycles
- 22.7 Retrosynthesis with Amines

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