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These videos aim to provide short, effective teaching of specific problem solving skills in organic chemistry.


Drawing Structures
Line Drawings “Hidden” Hydrogens Exercise: Condensed Formula (1)
Exercise: Condensed Formula (2)


Formal Charge
Atomic Charge Formal Charge Introduction Key Patterns
Exercise: NH4 Exercise: CN Exercise: CO3
Exercise: N3 Exercise: CH2N2 Exercise: O3
Exercise: CH3NO2 Exercise: Radicals/Carbenes Exercise: Hidden Hydrogens
Exercise: Hidden Lone Pairs Exercise: Allyl carbocation


Bond Rotations
The “Steering Wheel” Analogy Exercise 1 Exercise 2
Exercise 3 Exercise 4 Exercise 5


Nucleophilic Substitution
What is Substitution? Introduction to the SN2 (Experiments) The SN2 Mechanism
Exercise: Applying the SN2 Introduction to the SN1 (Experiments) The SN1 Mechanism
Exercise: Applying the SN1 Comparing the SN1 and SN2 What’s a Nucleophile?
What makes a good nucleophile? (1) What makes a good nucleophile? (2) What makes a good nucleophile? (3)
Solvents in SN1 and SN2 Reactions What makes a good leaving group? Making OH a good leaving group
Carbocation Stability The SN2 Reaction Energy Diagram The SN1 Reaction Energy Diagram
SN1 vs. SN2 Overview Exercise: SN2 (Leaving groups) Exercise: SN2 (Substrate)
Exercise: SN1 (Substrate) SN1 with rearrangement (1) SN1 with rearrangement (2)
SN1 with rearrangement (3)


Introduction to Elimination Zaitsev’s Rule How Heat Affects Elimination Reactions
The E1 Reaction E1 vs. SN1 E1 with rearrangement (1)
E1 with rearrangement (2) The E2 Reaction The E2 Reaction (Newman projection)
E2 in cyclohexanes E2 in cyclohexanes (2) Bulky bases
Comparing the E1 and E2 Mechanisms Comparing E1 and E2 Stereochemistry Exercise: Zaitsev’s rule


Introduction to Rearrangements Carbocation Stability (1) Carbocation Stability (2)
Hydride Shifts Alkyl Shifts

Acids and Bases
Lewis acids and Lewis bases 4 Components of every acid base reaction Strong and weak acids
The golden rule of acid base reactions Acidity (1) Charge Density Acidity (2) Electronegativity
Acidity (3) Polarizability Acidity (4) Resonance Acidity (5) Electron Withdrawing Groups
Acidity (6) Orbitals Acidity (7) Aromaticity Introduction to pKa
How to use a pKa table


Introduction to Resonance Unequal Resonance Forms Curved Arrrows
Evaluating Resonance (1) Charge Evaluating Resonance (2) Octets Evaluating Resonance (3) Negative Charge
Evaluating Resonance (4) Positive Charge Evaluating Resonance (5) Aromaticity Summary of Resonance (1)
Summary of Resonance (2) Common Mistakes (1) Common Mistakes (2)


Converting Fischer to Line Diagram Converting Line Diagram to Fischer Converting Newman to Line Drawing
How to draw an enantiomer R and S relationships A simple trick for R/S
The single swap rule Determining R/S on a Fischer projection Exercise: Enant/Diastereomer/Same (1)
Exercise: Enant/Diastereomer/Same (2) Exercise: Enant/Diastereomer/Same (3) Exercise: Enant/Diastereomer/Same (4)
Exercise: Enant/Diastereomer/Same (5)


Substitution Elimination Decision
SN1/SN2/E1/E2 (1) Overview SN1/SN2/E1/E2 (2) Substrate SN1/SN2/E1/E2 (3) Nucleophile/base
SN1/SN2/E1/E2 (4) Solvent SN1/SN2/E1/E2 (5) Temperature


Introduction to Reactivity
How Formal Charge Can Mislead Identifying reactive sites