The Grignard reaction is one of the most versatile methods for forming C–C bonds. Although the mechanism of action between Grignard reagents and carbonyl compounds is not yet fully understood, it is generally believed to proceed via either a "concerted mechanism" or a "radical mechanism." Experimental studies have shown that substrates with low electron affinity tend to undergo concerted reactions, whereas sterically demanding substrates and Grignard reagents with bulky groups tend to follow a radical pathway.
- Reactant: Grignard reagent and electrophile
- Products: Vary depending on the electrophile and Grignard reagent used
- Type of Reaction: Nucleophilic addition
- Bond formation: C–C
Lab Tips
-
The reaction is sensitive to air and moisture; both reactants and solvents must be pre-treated accordingly.
-
Acidic functional groups (e.g., alcohols, thiols, phenols, carboxylic acids, primary or secondary amines, terminal alkynes) are incompatible with Grignard reagents.
-
Reactivity of Grignard reagents: For the same alkyl group, RI > RBr > RCl >> RF; for the same halogen, ArCH₂X, CH₂=CHCH₂X > 3°RX > 2°RX > 1°RX > CH₂=CHX.
Kürti, L., Czakó, B. (2005). Strategic Applications of Named Reactions in Organic Synthesis; Background and Detailed Mechanisms. Burlington, MA: Elsevier Academic Press.
mechanism of reaction
Original Paper
- Grignard, V. C. R. Acad. Sci. 1900, 130 (2), 1322–1324
Top Citations
Related Products
- Allyl bromide, 98% (CAS 106-95-6)
- Iodomethane,99% (CAS 74-88-4)
- Vinyl bromide (CAS 593-60-2)
- Allylmagnesium bromide (CAS 1730-25-2)
- Vinylmagnesium bromide (CAS 1826-67-1)
- Methylmagnesium bromide, 3M in ether (CAS 75-16-1)
- Tetrahydrofuran, 99% (CAS 109-99-9)
艳 李
