GT
CHEM 2312 -
Organometallic Reactions KEY
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KEY Organometallic Reactions KEY H C C H H3C C C H NaNH2 NH3 liq BuLi THF Na H C C H3C C C Li Terminal alkynes are weak acids pKa approx 25 H C C H3C CH2 CH2 Br H3C CH2 CH2 CH3 Na C C H3C Hindered substrates 2 and 3 result in elimination instead of substitution H3C CH2 CH Br H3C CH2 CH C CH NaBr CH3 H3C C C H H C C H3C CH3 O 1 BuLi 3 H3O H3C C C H 2 O H3C C C HC C H3O O CH3 CH3 HO OH HC C CH3 CH3 MgBr OH H3C Ph MgBr OH OH O H3C O O O O O O O O THF 2 H3O 1 1 Et2O 2 H3O 1 BrMg CH3 Et2O 2 H3O OH OCH3 1 PhLi THF 2 H3O 1 MeLi THF OCH3 2 H3O 1 CH3 2CuLi THF 2 H3O OH CH3 OH OH CH3 CH3 CH3 OH OH CH3 CH3 CH3
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