Our New Book, “Practice Organic Mechanisms”, Is Out

Our New Book, “Practice Organic Mechanisms”, Is OutMarch 14, 2016

Today I’m delighted to announce a new book – Practice Organic Mechanisms, co-written with Dr. Michelle Sulikowski, Senior Lecturer of Organic Chemistry at Vanderbilt University. Practice Organic Mechanis…

Tagged as: mechanisms, practice organic mechanisms

The Heck, Suzuki, and Olefin Metathesis Reactions (And Why They Don’t Belong In Most Introductory Organic Chemistry Courses)

The Heck, Suzuki, and Olefin Metathesis Reactions (And Why They Don’t Belong In Most Introductory Organic Chemistry Courses)March 10, 2016

There has been a trend in recent years towards including transition metal catalyzed reactions in the introductory organic chemistry curriculum. The reactions most common covered are palladium catalyzed coupling react…

Tagged as: grubbs, heck, organometallics, rcm, suzuki

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

Gilman Reagents (Organocuprates): What They’re Used ForFebruary 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…

Tagged as: 1, 2-addition, 4-addition, conjugate addition, elongates, enones, Gilman, gilman reagents, Grignards, hard soft acids bases, hsab, organocuprates

Gilman Reagents (Organocuprates): How They’re Made

Gilman Reagents (Organocuprates): How They’re MadeJanuary 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…

Tagged as: alkyl halides, gilman reagents, organocopper, organocuprates, organometallics, reduction

Grignard Reactions And Synthesis (2)

Grignard Reactions And Synthesis (2)January 19, 2016

Here’s the summary for today’s post on synthesis incorporating Grignard reagents and oxidants: Synthesis Using Grignard Reagents (Part 2) In the last post we saw how to approach some fairly straightforward…

Tagged as: grignard, oxidation, retrosynthetic analysis, synthesis

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 impor…

Tagged as: grignard, grignard reagents, Grignards, primary alcohols, secondary alcohols, synthesis, synthetic planning, tertiary alcohols

Protecting Groups In Grignard Reactions

Protecting Groups In Grignard ReactionsDecember 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, al…

Tagged as: acetals, grignard reagents, organometallics, protecting groups

Reactions of Grignard Reagents

Reactions of Grignard ReagentsDecember 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 alk…

Tagged as: addition, epoxides, Grignards, organometallics

Organometallics Are Strong Bases

Organometallics Are Strong BasesNovember 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, carbon…

Tagged as: conjugate acid, conjugate base, deuterium, Grignards, organolithium, organometallic

Synthesis of Grignard and Organolithium Reagents

Synthesis of Grignard and Organolithium ReagentsNovember 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 mol…

Tagged as: grignard, organolithium, organometallics