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...]
The Three Classes of Nucleophiles
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...]
Learning vs. Memorization In Organic Chemistry
"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...]
Proton Transfers Can Be Tricky
(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...]
Keto-Enol Tautomerism: Key Points
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...]
Organic Chemistry Study Tips: Learn the Trends
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...]
Nucleophile attacks Electrophile
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...]