"86 Tricks to Ace Organic Chemistry" & "Ace Organic Chemistry Mechanisms with EASE" Table of Contents

"86 Tricks" Table of Contents

 

Chapter 1: Setting yourself up for Success

#1- Watch out for the Flunking Professor.  

#2- Study in packs—there is safety in numbers.  

#3-Take the course at a more opportune time.  

#4- Get away from the pre-meds.  

#5- Don't overemphasize the lab section.  

   

Chapter 2: Introductory Concepts  

#6-  Memorize your nomenclature and essential vocabulary.  

#7-Wouldn't formaldehyde by a different name smell just as sweet?  The difference between common names and IUPAC nomenclature.  

#8- Know the normal state for common organic atoms.  

#9- Fischer projections are a black tie affair.  

#10- Is it really that EZ.  Determining alkene geometry.  

#11- Master Resonance.  

#12- You Spin Me Right Round Baby, Right Round, Like a Record Baby  

#13- Size Matters: Resonance between equivalent atoms means equal bond lengths.  

#14- Good for nothing alkanes.  Lousy molecules  

#15- Paula Abdul was wrong.  In organic chemistry, LIKES attract.  

#16-Beware of the bad acid trip: Meet your strong acids.  

#17- Meet your strong nucleophiles.  

#18- They have worn out their welcome--Know your leaving groups.  

#19- If you don't start with chirality, you can't end with it.  

#20- Markovnikov was a Liar.  

#21- A different type of chemistry test.  Functional Group Tests  

#22- Is it E1, E2, SN1, SN2?  

#23-Why you should not stay on the straight and narrow (if you are counting carbon chains).  

#24-Arrows will point the way.  

#25- There are only 3 different mechanisms to know.  That's it, just 3 (kinda).  

#26-They have the internet on computers now??

   

Chapter 3: Organic Chemistry Strategy  

#27- Go to Home Depot and Get a Chemistry Toolbox.  

#28- It Takes Alkynes to Make the World Go Around (and to react with epoxides)  

#29- Four Organometallics to Rule Them All  

#30- Diels-Alder Reaction-Part 1: An Introduction  

#31- Let's Go Retro: Retrosynthetic Analysis  

#32- Overall EAS Strategy  

#33- EAS Strategy: Turn a meta into ortho/para and vice-versa.  

#34- EAS Strategy: conversion of alkyl groups to carboxylic acids.  

#35- EAS Strategy: In football, you need good blockers.  SO3 and X are our Blocking Groups  

#36- EAS Strategy: Long Chain Alkyl Groups from Wolff-Kishner or Reduction  

#37- EAS Strategy: Substituted toluenes came from toluene. Duh  

   

Chapter 4: Helpful Reactions, Hints, Clues  

#38: Want to impress your instructor? Start dropping names.  

#39- Enantiomers are Siblings, Diastereomers are Cousins, which makes Rotomers Your Dingy Aunt.  

#40- Benzylic and Allylic Leaving Groups are Better Than They Look.  

#41- Before You Die, You See the [Aromatic] Ring.  

#42- Eject! Eject!  Eject!: Carbonyls with an ejectable group are added to twice.  

#43- Hint: hv  means a radical is brewing.  

#44- T-butyl groups on cyclohexane means no ring flips .kinda.  

#45- Like Jerry Lewis asking for money, Lewis acids are always asking for electron density and can make electrophiles more electrophilic.  

#46- H2SO4 and HNO3: the good-cop/bad-cop of nitrations.  

#47- The Incredible Bulk: Bulky Bases.  

#48 –UFC 1221: Hoffman vs. Zaitsev, the Elimination.  

#49- Dude, where's my carbocation?  

#50- Free Radical Halogenation: The Molecular Handle.  

#51- My Three Reductions: Reduction Methods For Alkynes  

#52- Is a Halogen Squatting on Your Molecule.  Removing the unwanted halogen.  

#53- You don't want a D on your transcript, but you might want one on your molecule.  

#54- Diels-Alder Part 2: Regiochemistry and Stereochemistry  

#55- Diels-Alder Part 3: What Makes a Good Diels-Alder Reaction  

#56- It's an urban legend that SN1 reactions give completely racemic products.  

#57- What do you Amine you're getting rid of me?--How to eliminate an amine.  

#58- Why Didn't You Say Were Sendin  the Wolf?—The Wolff-Kishner Reduction  

#59- It Takes a Baeyer-Villiger to Raise a Child  

#60- Symmetric Diols Came From the Pinacol Reaction  

#61- Convert a nitro group into the aldehyde or ketone.  

#62- McMurry Reaction:  A reverse ozonolysis.  

#63- Role Reversal: Nitrile Hydration and the Letts Nitrile Synthesis  

#64- Role Reversal: Dihydroxylation and the Corey-Winter Olefination  

#65- Role Reversal: Halogens and Carboxylic Acids  

#66- Musical Double Bonds: Using catalytic I2.  

#67- Just Like Kevin Costner to Whitney Houston, Protecting Groups Are Chemical Bodyguards  

#68- Don't Hydrogenate That Aryl Ring!  You’ll Kill Us All!  

#69- It's as Easy as 1,2 Addition.  Or Is It 1,4 Addition?  

#70- Here's to Your Annulation, Mrs. Robinson: Musings on the Robinson Annulation.  

#71- Kinetic vs. Thermodynamic Enolates: You Choose the Winner of This Fight.  

#72- Where's Aldol?: Making an Aldol Reaction Work for You.  

#73- Acetoacetic Ester Synthesis: What You Need to Know In One Page or Less.  

#74- alpha-keto Esters Came From a Claisen Condensation (NOT the Claisen Rearrangement)  

#75 –Convert Ketones to Epoxides Fast  

#76- Two Ways to Open One Epoxide  

   

Chapter 5: Spectroscopy  

#77- SODAR is not just a drink mixer anymore  

#78- Splitting should be automatic, at least with NMR  

#79- O, M, P from the aromatic region of an NMR  

#80- Everything You Ever Wanted to Know About a 13C, But Were Afraid to Ask  

#81- There are Only Four Important IR Peaks.  

#82- Check Out the Cleavage On That Molecule  

#83- The Nitrogen Hint (Not a Rule)  

   

Chapter 6: Study Tips and Suggestions  

#84- Are You a Learner Like Socrates or a Memorizer Like a Super Computer?  

#85- What a Tangled Web We Weave.  

#86- Be a Chatty Patty and Talk Out Your Reactions.

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"EASE" Table of Contents  

Introduction:

The Language

Resonance  

Arrows Will Point the Way 

Functional Groups 

A Brief Preview of the EASE Method: 

 

Chapter 1 

STEP 1--“E” is for Electrophile: 

Electrophiles:  

Leaving groups create electrophilic sites: 

Nucleophiles:   

Step 2--“A” is for Acid:    

Acids:          

Acids from Unlikely Places: 

Lewis Acids:    

Bases:  

Step 3 --“S” is for Sterics:.  

Step 4 --“E” is for Electron Flow:  

 

Chapter 2 

Need to Know Mechanism #1: SN1   

Need to Know Mechanism #2: SN2  

Need to Know Mechanism #3: E1  

Need to Know Mechanism #4: E2  

Need to Know Mechanism #5: Electrophilic Aromatic Substitution

Intermediate Mechanism #1: Nucleophilic Addition to a Carbonyl.

Intermediate Mechanism #2: Alkene Addition 

Intermediate #3: Dieckmann Reaction 

7 More Mechanisms All-Stars Will Know: 

 

Chapter 3 

Easy Problem: What is the Mechanism?  

Intermediate Problem: What is the Mechanism?

Hard Problem: What is the Mechanism? 

Easy Problem: What is the Product?

Intermediate Problem: What is the Product? 

Real Chemistry You Have Never Seen Before:

 

Chapter 4 

Your Organic Chemistry Toolbox: 

Let’s Go Retro: Retrosynthesis 

Spiderwebs:  

 

Chapter 5  

Where the method will be less effective: 

Oxidation and Reduction: 

Radical Reactions:  

Organometallic Reagent Formation:  

 

Appendix 1:  

Answers To Supplemental Exercises