- 1. Getting Started
- 2. Organic Chemistry 101
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3. First Semester Topics
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Structure and Bonding
- Chemical Intuition
- Difficulty-in-organic-chemistry
- Atomic Orbitals
- Electron Configurations of Atoms
- Practice Time - Structure and Bonding 1
- Lewis Structures
- Drawing Lewis Structures Guide
- Valence Bond Theory
- Hybridization
- Polar Covalent Bonds
- Formal Charge
- Practice Time - Structure and Bonding 2
- Curved Arrow Notation
- Resonance
- Electrons behave like waves
- MO Theory Intro
- Rules of Thumb
- Structural Representations
- Acids/Base and Reactions
- Functional Groups
- Alkanes and Cycloalkanes
- Stereochemistry
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Alkenes and Addition Reactions
- Application - BVO (Brominated Vegetable Oil)
- E/Z and CIP
- Stability of Alkenes
- H-X Addition to Alkenes: Hydrohalogenation
- Practice Time - Hydrohalogenation
- X2 Addition to Alkenes: Halogenation
- HOX addition: Halohydrins
- Practice Time - Halogenation
- Hydroboration/Oxidation of Alkenes: Hydration
- Practice Time - Hydroboration-Oxidation
- Oxymercuration-Reduction: Hydration
- Practice Time - Oxymercuration/Reduction
- Oxidation
- Reduction
- Alkynes
- Alcohols and Alkyl Halides
- Aliphatic Substitutions (SN1/SN2)
- Dienes, Allylic and Benzylic systems
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Structure and Bonding
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4. Second Semester Topics
- Arenes and Aromaticity
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Reactions of Arenes
- Electrophilic Aromatic Substitution
- EAS-Halogenation
- EAS-Nitration
- Practice Time - Synthesis of Aniline
- EAS-Alkylation
- Practice Time - Friedel Crafts Alkylation
- EAS-Acylation
- Practice Time - Synthesis of Alkyl Arenes
- EAS-Sulfonation
- Practice Time - EAS
- Effect on Rate and Orientation
- Donation and Withdrawal of Electrons
- Regiochemistry in EAS
- Practice Time - Directing Group Effects
- Steric Considerations
- Synthesizing Poly-substituted Benzene's
- NAS - Addition/Elimination
- NAS - Elimination/Addition - Benzyne
- Alcohols and Phenols
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Ethers and Epoxides
- Intro and Occurrence
- Crown Ethers
- Preparation of Ethers
- Reactions of Ethers
- Practice Time - Ethers
- Preparation of Epoxides
- Reactions of Epoxides - Acidic Ring Opening
- Practice Time - Acidic Ring Opening
- Reactions of Epoxides - Nucleophilic Ring Opening
- Practice Time - Nucleophilic Ring opening
- Application - Epoxidation in Reboxetine Synthesis
- Application - Nucleophilic Epoxide Ring Opening in Crixivan Synthesis
- Naming Ethers and Epoxides
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Aldehydes and Ketones
- Naming Aldehydes and Ketones
- Practice Time - Naming Aldehydes/Ketones
- Nucleophilic addition
- Addition of Water - Gem Diols
- Practice Time - Hydration of Ketones and Aldehydes
- Addition of Alcohols - Hemiacetals and Acetals
- Acetal Protecting Groups
- Hemiacetals in Carbohydrates
- Practice Time - Hemiacetals and Acetals
- Addition of Amines - Imines
- Addition of Amines - Enamines
- Practice Time - Imines and Enamines
- Application - Imatinab Enamine Synthesis
- Addition of CN - Cyanohydrins
- Practice Time - Cyanohydrins
- Application - Isentress Synthesis
- Addition of Ylides - Wittig Reaction
- Practice Time - Wittig Olefination
- Carboxylic Acids and Derivatives
- Enols and Enolates
- Condensation Reactions
- 5. Spectroscopy - NMR, IR and UV
- 6. Mass Spectrometry
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7. General Chemistry
- Significant Figures
- Practice Time! Significant Figures
- Spreadsheets - Getting Started
- Spreadsheets - Charts and Trend lines
- Standard Deviation
- Standard Deviation Calculations
- Factor Labels
- Practice Time! - Factor Labels
- Limiting Reagent Problem
- Percent Composition
- Molar Mass Calculation
- Average Atomic Mass
- Empirical Formula
- Initial Rate Analysis
- Practice Time! Initial Rate Analysis
- Solving Equilibrium Problems with ICE
- Practice Time! Equilibrium ICE Tables
- Le Chatelier's
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8. Organic Chemistry Lab
- 9. General Chemistry Lab
- 10. Named Reactions
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11. Reagents
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12. Question Of The Day
- 13. Tutorials
- 14. Ask a Question
Clear History
NAS - Elimination/Addition - Benzyne
Introduction to NAS
In the presence of a more powerful base/nucleophile or at higher temperatures a different mechanism for NAS can occur. While studying NAS reactions, researcher encountered some unexpected regichemistry.
When they labeled the carbon attached to the Cl atom with a 13C they observed the following two products in equal amounts.
They proposed the following elimiation/addition sequence and proved it by traping the benzyne intermediate.
The benzyne intermediate was trapped with 1,3-butadiene via a Diels-Alder reaction. See if you can predict the Diels Alder product.
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