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Can Grignards be chiral? I've seen them drawn as ionic structures in class. I've also seen little asterisks on certain positions of Grignards (a common designation of chirality). So this begs the question - are Grignards chiral?

From what I understand Grignards are best described as polar covalent rather than ionic, but that still leaves one more question: can ionic compounds be chiral?

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I read the question as asking whether a stereocenter bearing a C-Mg bond will keep its configuration. The answer is yes, but not indefinitely. Unfunctionalized (alkane) Grignards of this type racemize/epimerize with a half life on the order of hours. Specific compounds will have more or less stability. By analogy to organolithium compounds, I would expect having Lewis basic atoms in the proximity to stabilize the configuration. I'm not sure if this is still an active field of research, but it certainly was for a long time. Try searching "configurational stability of Grignard reagents" or similar search terms.

There's an additional complication with these chiral Grignard reagents: they can't be prepared by the usual method of oxidative addition of Mg(0) to an alkyl halide. The mechanism of that reaction goes by a single electron transfer, through a radical intermediate, destroying any stereocenter. Chiral Grignards have to be synthesized using less direct methods.

Ref: Side Reactions in Organic Synthesis: A Guide to Successful Synthesis Design, pp. 200-202.

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