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"86 Tricks" Table of Contents
Chapter 1: Setting yourself up for Success
#1- Watch out for the Flunking Professor.
#2- Study in packsthere 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! Youll 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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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