Unit 24: Carbon–Carbon Bond-Forming Reactions & Organometallics

This unit turns organic chemistry from functional-group interconversion into real synthesis by focusing on the methods that create new carbon frameworks deliberately.

• Choose among Grignard, organolithium, Gilman, and palladium-catalyzed coupling methods for common C–C bond disconnections.
• Predict 1,2 versus 1,4 addition behavior for organometallic reagents.
• Use organometallic additions to carbonyls and epoxides to lengthen carbon chains predictably.
• Recognize when Suzuki, Sonogashira, Heck, or related couplings solve an aryl/vinyl bond-forming problem efficiently.

Checkpoint Questions

Q: What product class results when a Grignard reagent adds to formaldehyde and is then protonated?

A: A primary alcohol that is one carbon longer than the Grignard alkyl group.

Q: Why might a chemist choose Suzuki coupling instead of trying to build a biaryl with a strongly basic organolithium?

A: Suzuki coupling usually tolerates far more functional groups and avoids the harsh basicity of organolithium chemistry.