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Let’s map out all of the reactions we’ve learned in this section on aromatic rings + substituents.Also included is a few reactions we actually haven’t covered yet – such as diazonium salt formation and Sandmeyer reactions. These are...
What’s not to love about the cyanide ion?OK, OK, it’s a deadly poison, and should be treated extremely carefully in the lab.But besides that,it’s an excellent nucleophile that can react with a wide variety of electrophiles, resulting in a...
The Diels-Alder is an onion, and we just keep peeling back the layers. Today’s post is about regioselectivity in the Diels-Alder. Quick summary:“Regioselectivity” In The Diels-Alder ReactionSo far in the Diels-Alder, we’ve seen examples...

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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...