organometal

organometal - Alkyl Halides Organometallic Reagents 1)...

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Alkyl Halides Organometallic Reagents 1) Grignard reacts with: RX + Mg 0 ether RM g II X H + , D + electrophile (H 2 O, D 2 O) or THF O O now nucleophilic HO 1 2 3 4 6 5 disconnect between carbons 2 and 3 or R R R H 1 HO 6 2 3 5 4 O MgBr + 1 2 6 3 4 5 MgBr O 6 5 1 3 2 4 H 2 O HO 6 5 1 3 2 4
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a) Li 2) Organolithium n-butyl lithium H 3 C b) 2 H 3 CL i + Cu I ether CuLi + Li I H 3 C Formation H 3 C 2 2 CuLi + I ether + Li I + CH 3 Cu H 3 C 1 1 any alkyl group Reaction Remember pKa of alkyl group is ~50 (very high) so deprotonated alkyl group is VERY basic H 3 CC H 2 NaBr H 2 H 3 C C Li very basic carbons will react w/ acidic proton like
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organometal - Alkyl Halides Organometallic Reagents 1)...

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