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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” HydrogensExercise: Condensed Formula (1)
Exercise: Condensed Formula (2)


Formal Charge
Atomic ChargeFormal Charge IntroductionKey Patterns
Exercise: NH4Exercise: CNExercise: CO3
Exercise: N3Exercise: CH2N2Exercise: O3
Exercise: CH3NO2Exercise: Radicals/CarbenesExercise: Hidden Hydrogens
Exercise: Hidden Lone PairsExercise: Allyl carbocation


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


Nucleophilic Substitution
What is Substitution?Introduction to the SN2 (Experiments)The SN2 Mechanism
Exercise: Applying the SN2Introduction to the SN1 (Experiments)The SN1 Mechanism
Exercise: Applying the SN1Comparing the SN1 and SN2What’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 ReactionsWhat makes a good leaving group?Making OH a good leaving group
Carbocation StabilityThe SN2 Reaction Energy DiagramThe SN1 Reaction Energy Diagram
SN1 vs. SN2 OverviewExercise: SN2 (Leaving groups)Exercise: SN2 (Substrate)
Exercise: SN1 (Substrate)SN1 with rearrangement (1)SN1 with rearrangement (2)
SN1 with rearrangement (3)


Introduction to EliminationZaitsev’s RuleHow Heat Affects Elimination Reactions
The E1 ReactionE1 vs. SN1E1 with rearrangement (1)
E1 with rearrangement (2)The E2 ReactionThe E2 Reaction (Newman projection)
E2 in cyclohexanesE2 in cyclohexanes (2)Bulky bases
Comparing the E1 and E2 MechanismsComparing E1 and E2 StereochemistryExercise: Zaitsev’s rule


Introduction to RearrangementsCarbocation Stability (1)Carbocation Stability (2)
Hydride ShiftsAlkyl Shifts

Acids and Bases
Lewis acids and Lewis bases4 Components of every acid base reactionStrong and weak acids
The golden rule of acid base reactionsAcidity (1) Charge DensityAcidity (2) Electronegativity
Acidity (3) PolarizabilityAcidity (4) ResonanceAcidity (5) Electron Withdrawing Groups
Acidity (6) OrbitalsAcidity (7) AromaticityIntroduction to pKa
How to use a pKa table


Introduction to ResonanceUnequal Resonance FormsCurved Arrrows
Evaluating Resonance (1) ChargeEvaluating Resonance (2) OctetsEvaluating Resonance (3) Negative Charge
Evaluating Resonance (4) Positive ChargeEvaluating Resonance (5) AromaticitySummary of Resonance (1)
Summary of Resonance (2)Common Mistakes (1)Common Mistakes (2)


Converting Fischer to Line DiagramConverting Line Diagram to FischerConverting Newman to Line Drawing
How to draw an enantiomerR and S relationshipsA simple trick for R/S
The single swap ruleDetermining R/S on a Fischer projectionExercise: 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) OverviewSN1/SN2/E1/E2 (2) SubstrateSN1/SN2/E1/E2 (3) Nucleophile/base
SN1/SN2/E1/E2 (4) SolventSN1/SN2/E1/E2 (5) Temperature


Introduction to Reactivity
How Formal Charge Can MisleadIdentifying reactive sites