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Previously [see: Nucleophilic Aromatic Substitution] we saw that electron-poor aromatic rings containing a leaving group can undergo substitution with electron-rich nucleophiles. We saw that the mechanism proceeds through addition of a nucleophile to the aromatic...
“How Are We Related, Again?”A few weeks ago, at a family reunion in Ontario, I introduced my relatives to the joy of liquid nitrogen ice cream. My cousins were there, as were many of their children. So were a few of my dads’ cousins. Being...
The Little Known Fact About Cyclopentadiene THEY Don’t Want You To Know AboutLet’s talk about cyclopentadiene, a commonly used diene for Diels-Alder reactions that, by the way, comes up all the time on tests and exams. Like here:Gather around closely...

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In the previous post in this series, “On Conjugation and Resonance“, I warned that in order to gain a deeper understanding of some of the concepts ahead, we’regoing to need to go into MO theory.But before we do… shall we talk about dating?...
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...
Last time we talked about how some interesting electronic effects can lead to unexpected results in organic chemistry. Today we look at three examples of how steric factors can lead to unexpected products (or lack of products). The last example is a case where...

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A list of small, useful things (links): Anyone facing a writing deadline (looking at you, thesis writers) (looking right back at you, CJ - ed.) should read Dan Drezner's post on writing a non-fiction book. I have been remiss in not linking to...
A bit of a lack of exciting syntheses so far this week, so here's some methodology and random reflections and recollections.I don't mind that we don't get told the whole truth as undergraduates, because most of us can't handle the truth (well, not all of it)....
This is a loose transcript of the Syllabus Day speech I gave my Organic Chemistry I class on the first day of fall semester this week. Organic Chemistry I is the first of a two semester sequence at my small, Midwest, liberal arts university. Our five organic...