Key Terms

• alkyl halide
• allylic
• carbanion
• delocalized
• Gilman reagent (LiR2Cu)
• Grignard reagent (RMgX)
• organohalide
• organometallic

Summary of Reactions 10 • Summary of Reactions 10 • Summary of Reactions

No stereochemistry is implied unless specifically indicated with wedged, solid, and dashed lines.

• Preparation of alkyl halides
• From alkenes by allylic bromination (Section 10.3)

• From alcohols (Section 10.5)
• Reaction with HX

• Reaction of 1° and 2° alcohols with SOCl2

• Reaction of 1° and 2° alcohols with PBr3

• Reaction of 1° and 2° alcohols with HF–pyridine

• Reactions of alkyl halides
• Formation of Grignard (organomagnesium) reagents (Section 10.6)

• Formation of Gilman (diorganocopper) reagents (Section 10.7)

• Organometallic coupling (Section 10.7)

• Diorganocopper reaction

• Palladium-catalyzed Suzuki–Miyaura reaction