Master Organic Chemistry

The Lies We Tell

August 10, 2011 By James Ashenhurst 10 Comments

Zed Shaw teaches a course in writing Python called "Python the Hard Way". Because the hard way is easier, he says. In the end, he's right. If you really want to learn organic chemistry, the hard way is easier. In graduate school I had to un-learn a lot of the half-truths I was taught in the … [Read more...]

Filed Under: Teaching Tagged With: bredt's rule, Friedel-Crafts, hyperconjugation, Key Concepts, kmno4, lies, organic chemistry is hard, shortcuts, teaching

The Three Classes of Nucleophiles

March 4, 2011 By James Ashenhurst 7 Comments

I know I've said this before, but a whole lot of organic chemistry can be boiled down to "nucleophile attacks electrophile". A nucleophile is a compound that can donate a pair of electrons to (you guessed it) an electrophile, which results in the formation of a chemical bond. If you look … [Read more...]

Filed Under: Alkenes, Organic Chemistry 1, Organic Chemistry 2, Organic Reactions, Understanding Electron Flow Tagged With: carbocations, curved arrows, electron density, electronegativity, electrophiles, Key Concepts, lone pairs, nucleophiles, pi bonds, resonance, SN2 reactions

Learning vs. Memorization In Organic Chemistry

February 24, 2011 By James Ashenhurst 5 Comments

"Learn the concepts! Don't memorize!". It's one of the most common sentences found in the many examples of instructors' essays on "How to Succeed in Organic Chemistry". But what does it really mean? It took me a long time to figure that out. But I'm going to try to explain it with an … [Read more...]

Filed Under: Organic Chem Study Tips, Teaching Tagged With: alkynes, applying concepts, Key Concepts, learning vs memorization, memorization, sp, study tips

Proton Transfers Can Be Tricky

May 19, 2010 By James Ashenhurst 4 Comments

(part 3 of a series on reactions of neutral nucleophiles with carbonyls) Here's a question for you. How would you draw a mechanism for the following reaction? Well, there's two ways to draw it. The 1,2-addition, that comes first. That's clear. Now what? Well, you could draw the reaction … [Read more...]

Filed Under: Aldehydes, Esters, Ketones, Organic Chemistry 2 Tagged With: addition, carbonyls, elimination, Key Concepts, least motion, leaving groups, mechanisms, proton transfer

Keto-Enol Tautomerism: Key Points

April 12, 2010 By James Ashenhurst 21 Comments

Aldehydes and ketones are  somewhat lycanthropic chemical species.  Take acetone. It behaves as a garden-variety polar aprotic solvent, which makes it a useful medium for SN2 reactions;  it reacts readily with nucleophiles like enolates, Grignards, and amines; and is several pKa units less acidic … [Read more...]

Filed Under: Aldehydes, Chemical Bonds, Esters, Ketones, Organic Chemistry 2 Tagged With: aldehydes, carbonyls, electrophiles, enol, enolates, hydrogen bonding, ketones, Key Concepts, nucleophiles, tautomerism, tautomers

Organic Chemistry Study Tips: Learn the Trends

April 9, 2010 By James Ashenhurst 10 Comments

This is the first in a series of occasional articles about useful strategies and tactics for studying organic chemistry.  Here is a general template for a short exam question in organic chemistry: As you change [increase/decrease] variable X, you change [increase/decrease] variable Y. … [Read more...]

Filed Under: Organic Chem Study Tips, Organic Chemistry 1, Organic Chemistry 2 Tagged With: concepts, exams, Key Concepts, memorization, studying, trends

Nucleophile attacks Electrophile

April 1, 2010 By James Ashenhurst 5 Comments

My Ph.D supervisor's Ph.D. supervisor was quoted once as saying, "basically, all organic chemistry reactions boil down to nucleophile attacks electrophile." Think about it for a minute. When you expand your concept of nucleophile beyond those species that will react with an alkyl halide in an SN2 … [Read more...]

Filed Under: Alcohols, Alkyl Halides, Chemical Bonds, Organic Chemistry 1, Understanding Electron Flow, Where Electrons Are Tagged With: electron rich, electronegativity, electrophiles, Key Concepts, nucleophiles, opposite charges attract, rate

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