Gilman test

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The Gilman test is a chemical test for the detection of Grignard reagents and organolithium reagents. [1] [2]

The Gilman reagent "is an organometallic compound used in organic chemistry for the formation of carbon-carbon bonds through coupling reactions. It is a powerful tool in the synthesis of complex organic molecules." [3]

A 0.5 mL sample is added to a 1% solution of Mischler's ketone in benzene or toluene. To this solution is added 1 mL of water for hydrolysis to take place and then several drops of 0.2% iodine in glacial acetic acid. If the color of the resulting solution becomes a greenish-blue then the original sample did contain the organometallic species.

References

  1. Henry Gilman and F. Schulze (1925). "A qualitative color test for the Grignard reagent". J. Am. Chem. Soc. 47 (7): 2002–2005. doi:10.1021/ja01684a032.
  2. "Cyclohexylcarbinol". Organic Syntheses . 1941; Collected Volumes, vol. 1, p. 188.
  3. "Gilman Reagent Definition - Organic Chemistry Key Term | Fiveable". fiveable.me. Retrieved 2025-12-08.