An Unsung Classic

I recently discovered Miguel Alonso’s The Art of Problem Solving in Organic Chemistry among my research group’s collection. This book makes a great companion to Grossman’s The Art of Writing Reasonable Organic Reaction Mechanisms, which is more exhaustive but, in my opinion, less compelling in the problems it presents. Alonso’s book is chock full of compelling mechanism problems, which will require even the most astute organic chemist to bust out paper and pencil and start drawing molecules. Perhaps the only downside of the book is its misleading title, which suggests generalized organic chemistry problem solving—the book is limited to mechanism problems, so don’t look to it for other subjects. It’s also a shame that this book hasn’t seen an update since the late 80’s…organometallic and radical chemistry are hard to find in its pages.

School has been crazy recently. I promised a post on chemoinformatics in education, and I will deliver soon…just not today 🙂 I’ll leave you with an interesting problem from Alonso’s book, inspired by a recent post on MasterOrganicChemistry.com. Can you provide mechanisms that explain the formation of all observed products in the reaction below?

Grignard reagents and propargyl chlorides

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