Grignards

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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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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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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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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Opening Of Epoxide With Base

Opening Of Epoxide With Base

February 10, 2015

Opening of epoxides with base a summary of what we talk about today: In the last post we discussed the reactions of epoxides under acidic conditions and saw how they resembled the “3-membered ring” family of alkene mechanisms. We left off by noting that the reaction of the epoxide (shown above)  with NaOH in H2O […]

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Common Mistakes with Carbonyls: Carboxylic Acids… Are Acids!

May 20, 2011

Carboxylic acids… are acids. I know that seems obvious. But it’s a near certainty that students taking Org 2 for the first time will forget this occasionally. Here are two common mistakes that I see *all the time*. 1) Reactions of Grignard reagents with carboxylic acids. Grignard reagents (with the general structure RMgBr) are great […]

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