Organic Chemistry 2

Gilman Reagents (Organocuprates): What They’re Used For

Gilman Reagents (Organocuprates): What They’re Used For

February 5, 2016

Last time we talked about how to make Gilman reagents (organocuprates). In this post, we’ll talk about what they’re actually used for. Here’s a summary for today: So what are Gilman Reagents Used For Anyway? As I hinted at last time, Gilman reagents provide an interesting contrast with Grignard and organolithium reagents. Remember all those […]

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Gilman Reagents (Organocuprates): How They’re Made

Gilman Reagents (Organocuprates): How They’re Made

January 29, 2016

Here’s the summary for today’s post: Organometallics: What About The Rest Of The Periodic Table? In this whole series on organometallics so far has covered exactly TWO metals: lithium and magnesium (with a very brief head-nod to sodium and the comparatively useless Wurzt Wurtz reaction.) There are dozens of other metals on the periodic table. What […]

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Synthesis Using Grignard Reagents (1)

Synthesis Using Grignard Reagents (1)

January 13, 2016

Here’s the bottom line for today’s post on solving synthesis problems involving Grignard reagents. Solving Synthesis Problems Involving Grignard Reagents Now that we’ve covered some of the most important reactions of Grignard reagents, it’s time to actually apply this knowledge to practical matters. And by practical matters, I mean synthesis. After all, the point of learning […]

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Protecting Groups In Grignard Reactions

Protecting Groups In Grignard Reactions

December 16, 2015

Now that we’ve gone over the most useful reactions of Grignard reagents – addition to epoxides, aldehydes, ketones, and esters – let’s go back to the topic of how to make Grignard reagents, albeit with a twist. Here’s the summary for today’s post: Introducing Yet Another Way To Royally Screw Up Making A Grignard Reagent In a […]

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Reactions of Grignard Reagents

Reactions of Grignard Reagents

December 10, 2015

Here’s the summary for today’s post: So far in this series we’ve introduced organometallic compounds and said that their carbons tend to be nucleophilic. We’ve learned how to make them from alkyl, alkenyl or aryl halides (along with some ways not to make them!) and saw that they are very strong bases. So what now? […]

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Organometallics Are Strong Bases

Organometallics Are Strong Bases

November 13, 2015

Last post we talked about how to make certain organometallics, specifically Grignard and organolithium reagents. One thing we saw is that it’s useful to think of them as “carbanions”, that is, carbons bearing a negative charge. We’ve also seen that carbanions tend to be strong bases, as they are the conjugate bases of alkynes (pKa […]

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Synthesis of Grignard and Organolithium Reagents

Synthesis of Grignard and Organolithium Reagents

November 9, 2015

In the last post we introduced the concept of organometallic compounds – molecules where carbon is bound to a less electronegative atom such as Li, Mg, Cu, and many other metals. We said that carbon in these molecules tends to be electron-rich and thus have nucleophilic character, in contrast to functional groups such as alkyl […]

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What’s An Organometallic?

What’s An Organometallic?

October 28, 2015

Quick summary for today – the first in a new series on organometallic compounds: Previously on MOC we’ve discussed how important dipoles are in determining the reactivity of a molecule. Wait: dipoles, you might ask. How do we determine a dipole again?  Let’s start this series by making sure we’re clear on this, because it will be […]

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Intramolecular Reactions of Alcohols and Ethers

Intramolecular Reactions of Alcohols and Ethers

June 12, 2015

“Intramolecular Reactions Make Me Crumple Into The Fetal Position Crying For My Mommy” Here’s a topic which doesnt really fit neatly in with what we’ve discussed before but it’s essential to any discussion of alcohols and ethers. Intramolecular reactions.  Here’s the executive summary: Intramolecular reactions [i.e. reactions where two functional groups in a molecule react […]

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Demystifying Alcohol Oxidations

Demystifying Alcohol Oxidations

May 21, 2015

Today’s post in a nutshell: The Familiar Key Step At The Heart Of (Almost) All Alcohol Oxidation Reactions When I was learning organic chemistry I remember the reagents for oxidation reactions completely coming out of left field. KMnO4, K2Cr2O7, PCC, CrO3, Swern, Dess—Martin ? Hold on. Where did these reagents come from? How do they […]

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