Avoid These Resonance Mistakes

• “Initial Tails” and “Final Heads”
• 3 Ways To Make OH A Better Leaving Group
• A Simple Formula For 7 Important Aldehyde/Ketone Reactions
• Acetoacetic
• Acids (Again!)
• Activating and Deactivating
• Actors In Every Acid Base Reaction
• Addition – Elimination
• Addition Pattern 1 – Carbocations
• Addition pattern 2 – 3 membered rings
• Addition Reactions
• Aldehydes And Ketones – Addition
• Alkene Pattern #3 – The “Concerted” Pathway
• Alkyl Rearrangements
• Alkynes – 3 Patterns
• Alkynes: Deprotonation and SN2
• Amines
• Aromaticity: Lone Pairs
• Avoid These Resonance Mistakes
• Best Way To Form Amines
• Bulky Bases
• Carbocation Stability
• Carbocation Stability Revisited
• Carboxylic Acids are Acids
• Chair Flips
• Cis and Trans
• Conformations
• Conjugate Addition
• Curved Arrow Refresher
• Curved Arrows
• Decarboxylation
• Determining Aromaticity
• Diels Alder Reaction – 1
• Dipoles: Polar vs. Covalent Bonding
• E2 Reactions
• Electronegativity Is Greed For Electrons
• Electrophilic Aromatic Substitution – Directing Groups
• Elimination Reactions
• Enantiocats and Diastereocats
• Enolates
• Epoxides – Basic and Acidic
• Evaluating Resonance Forms
• Figuring Out The Fischer
• Find That Which Is Hidden
• Formal Charge
• Frost Circles
• Gabriel Synthesis
• Grignards
• Hofmann Elimination
• How Acidity and Basicity Are Related
• How Are These Molecules Related?
• How Stereochemistry matters
• How To Stabilize Negative Charge
• How To Tell Enantiomers From Diastereomers
• Hybridization
• Hybridization Shortcut
• Hydroboration
• Imines and Enamines
• Importance of Stereochemistry
• Intermolecular Forces
• Intro to Resonance
• Ketones on Acid
• Kinetic Thermodynamic
• Making Alcohols Into Good Leaving Groups
• Markovnikov’s rule
• Mechanisms Like Chords
• Mish Mashamine
• More On The E2
• Newman Projections
• Nucleophiles & Electrophiles
• Nucleophilic Aromatic Substitution
• Nucleophilic Aromatic Substitution 2
• Order of Operations!
• Oxidation And Reduction
• Oxidative Cleavage
• Paped
• Pi Donation
• Pointers on Free Radical Reactions
• Protecting Groups
• Protecting Groups
• Proton Transfer
• Putting it together (1)
• Putting it together (2)
• Putting it together (3)
• Putting the Newman into ACTION
• Reaction Maps
• Rearrangements
• Recognizing Endo and Exo
• Redraw / Modify
• Robinson Annulation
• Robinson Annulation Mech
• Sigma and Pi Bonding
• SN1 vs SN2
• sn1/sn2 – Putting It Together
• sn1/sn2/e1/e2 – Exceptions
• sn1/sn2/e1/e2 – Nucleophile
• sn1/sn2/e1/e2 – Solvent
• sn1/sn2/e1/e2 – Substrate
• sn1/sn2/e1/e2 – Temperature
• Stereochemistry
• Strong Acid Strong Base
• Strong And Weak Oxidants
• Strong and Weak Reductants
• Stronger Donor Wins
• Substitution
• Sugars (2)
• Synthesis (1) – “What’s Different?”
• Synthesis (2) – What Reactions?
• Synthesis (3) – Figuring Out The Order
• Synthesis Part 1
• Synthesis Study Buddy
• Synthesis: Walkthrough of A Sample Problem
• Synthesis: Working Backwards
• t-butyl
• Tautomerism
• The 4 Actors In Every Acid-Base Reaction
  • Conjugation
• The Claisen Condensation
• The E1 Reaction
• The Inflection Point
• The Meso Trap
• The Michael Reaction
• The Nucleophile Adds Twice (to the ester)
• The One-Sentence Summary Of Chemistry
• The Second Most Important Carbonyl Mechanism
• The Single Swap Rule
• The SN1 Reaction
• The SN2 Reaction
• The Wittig Reaction
• Three Exam Tips
• Tips On Building Molecular Orbitals
• Top 10 Skills
• Try The Acid-Base Reaction First
• Two Key Reactions of Enolates
• What makes a good leaving group?
• What Makes A Good Nucleophile?
• What to expect in Org 2
• Work Backwards
• Zaitsev’s Rule

A good friend of mine once told me, “smart people learn from their own mistakes. But geniuses learn from the mistakes of others.” (He is a genius: I am very much not).

Here’s 3 common mistakes to avoid when drawing resonance forms.

1. Make sure you haven’t gained or lost electrons or atoms. Everything should balance!

2. Make sure you haven’t moved any hydrogens around (this is surprisingly easy to do). Remember that you’re only allowed to break double bonds, not single bonds.

3. Make sure you don’t break the octet rule while drawing your arrows, or draw weird arrows that don’t make sense (like putting the tail at a positive charge)

Tomorrow: an important lesson in Finding That Which Is Hidden.

Thanks for reading! James

P.S. Common mistakes: How not to draw resonance curved arrows