Organic Chemistry
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.