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Here’s what we’ve learned about the Diels Alder reaction so far: [previous post in this series]3 pi bonds are always broken2 sigma bonds and a pi bond are always formed, resulting in a new six-membered ringelectron withdrawing groups on the dienophile...
Last post in this series on reactions of aromatic groups we introduced activating and deactivating groups in Electrophilic Aromatic Substitution (EAS). We learned that electron-donating substituents on the aromatic ring increase the reaction rate and electron-withdrawing...
The Hofmann Elimination is an elimination reaction that forms C-C double (pi) bonds that specifically occurs when the leaving group is NR3 [note]It proceeds through an E2 mechanism. Although the key concepts are no different than one learns in the chapter on...

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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...