Ch_322b_12.10

Ch_322b_12.10 - notable exception are the sodium alkynides,...

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Organolithium Reagents Organolithium reagents, R-Li, react with carbonyl compounds in a similar manner as Grignard reagents. Overall, there is parallel reactivity of RMgX and RLi reagents. R:Li δ− δ + + C=O R-C-O-Li lithium alkoxide salt H 3 O + R-C-O-H alcohol Organolithium reagents are also very strong bases and must be prepared and used in "dry" ether solvents or hydrocarbon solvents. They usually are more reactive than the corresponding Grignard reagents.
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Organosodium Compounds Because of their very great reactivity, R: - Na + compounds often undergo side reactions and have limited synthetic value. One
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Unformatted text preview: notable exception are the sodium alkynides, RC C: Na.-+ Preparation These organosodium compounds are prepared by proton exchange between terminal alkynes and sodium amide: RC C-H + Na + :NH 2-: pK a 25 ~ ~ RC C: Na +-+ :NH 3 pK a = 38 An Example of a Sodium Alkynide Addition Reaction CH 3 C CH NaNH 2 ether solvent CH 3 C C: Na +-CH 3 C C: Na +-sodium propynide + C=O CH 3 CH 3 CH 3 C C-C-O-CH 3 CH 3 Na + sodium alkoxide salt H 3 O + workup CH 3 C C-C-OH CH 3 CH 3 1,1-dimethyl-2-butyn-1-ol or 2-methyl-3-pentyn-2-ol...
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Ch_322b_12.10 - notable exception are the sodium alkynides,...

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