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Unformatted text preview: alcohol to an alkyl halide: R OH + HX R X + H 2 O (S N 1) ( X = Cl , Br , or I ) to synthesize a Grignard reagent: RX + Mg R MgX , X = Cl , Br , or I to synthesize an alkyl lithium: RX + 2 Li RLi + LiX to synthesize an organocuprate: 2 RLi + CuI R 2 CuLi + LiI Organocuprates can act as nucleophiles in an S N 2 reaction: R 2 CuLi + RX R-R Grignards and alkyl lithiums, in contrast, cannot act as S N 2 nucleophiles. Synthetic utility: Defunctionalizes, adds carbon-carbon sigma bonds. Some courses may not cover organocuprates. 1 www.freelance-teacher.com organic chemistry: R-and H-using R-to attack carbonyls and epoxides reactions: synthetic utility: Form carbon-carbon bonds. RMgX + carbonyl forms a new C-C bond, with an O-on the C that was attacked. RMgX + epoxide forms a new C-C bond, with an O-on the C next to the C that was attacked. 2 www.freelance-teacher.com...
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