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The azide ion(N3) is one of those chemical entities that just plain looksweird.Three nitrogens in a row?checkTwo negative charges and a positive charge, for a net charge of 1 ?checkStable?check (as long as it’s treated gently).As it turns out, the azide...
Today we’ll be going through two reactions on alkyl groups adjacent to aromatic rings: benzylic bromination and benzylic oxidation. Here’s the quick summary:Alkyl Groups = RoughageIn nutrition, “roughage” is what you call all the cellulose...
An Introduction To Simple Peptide SynthesisIn a recent post [Amides: Synthesis, Properties, and Nomenclature] we went through 3 common ways of making amides:Adding amines to acyl halides / anhydridesPartial hydrolysis of nitrilesCoupling of carboxylic acids...

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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...