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Chapter 1: Setting Yourself Up for Success
#1- How to get an “A” (or just pass) Organic Chemistry.
#2- Study in packs—there is safety in numbers.
#3-Take the course at a more opportune time.
#4- Flashcards can be your new BFF.
#5- Don’t over-emphasize 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- In organic chemistry, “likes dissolve likes”.
#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. A dirty, smelly 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 the hardware store and get a chemistry toolbox.
#28- It takes alkynes to make the world go ‘round (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: “h” 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.
#46- H2SO4 and HNO3: The good-cop/bad-cop of nitrations.
#47- The Incredible Bulk: Bulky bases.
#48- 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- The 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 the Secret Service, 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- β-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 NMR, 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.