Wheel of Grignard Reactions

The Grignard reagent is synthetically versatile as the organomagnesium compound can react with a variety of electrophiles.


The mechanism is not well-understood and most likely involves a single electron transfer (SET).



Wheel of Grignard reactions: Click/tap to enlarge the image


Substrates -> Products (on the infographic):

  1. Alcohols or Water -> Alkanes
  2. Epoxides -> Alcohols
  3. Formaldehyde -> Primary alcohols
  4. Aldehydes -> Secondary alcohols
  5. Ketones -> Tertiary alcohols
  6. Imines -> Secondary amines
  7. Carbon dioxide (or disulfide) -> Carboxylic (or dithiocarboxylic) acids
  8. Acyl chlorides (1 eq) -> Ketones
  9. Acyl chlorides (excess) -> Tertiary alcohols
  10. Formates -> Secondary alcohols
  11. Esters -> Tertiary alcohols
  12. Amides -> Ketones
  13. Nitriles -> Ketones
  14. Carbonates -> Tertiary alcohols
  15. Orthoesters -> Aldehydes
  16. Alkyl halides -> Alkanes


& others


The substrate must not have any acidic groups. The reactions require dry solvents such as THF (Tetrahydrofuran) (for both, look at the reaction #1).


What other wheel(s) 🎡 of organic reactions would you like to see❓ Questions❓ Let Chemaficionado know in the comments below or at mychemistryhomework@gmail.com❗


Reference:

Valiulin, R. Organic Chemistry: 100 Must-Know Mechanisms; De Gruyter: Berlin, 2023.

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