Ch_322b_12.07

Ch_322b_12.07 - Reactions of Organolithium and...

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Reactions of Organolithium and Organomagnesium Halides These organometallic reagents are strong bases and good nucleophiles . This reactivity is in accord with the carbanionic character of the carbon atom: C Li !" ! + C MgX !" ! + Reactions as Bases These organometallic reagents react rapidly with water and alcohols: R-MgX + H OR' pKa ~ ~ 16 stronger base stronger acid R- H + ROMgX pKa > ~ 40 weaker base weaker acid R-Li + H OR' R- H + ROLi Reactions with other "Acids" R'C C- H pKa ~ ~ 25 + R-MgX R- H R'C C-MgX + R'-N- H : R'' pKa ~ ~ 38 + R-Li R- H + R'-N: Li R'' - +
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Nucleophilic Additions of Grignard Reagents Oxiranes (Epoxides) These three-membered cyclic ethers are highly reactive towards nucleophiles because of the ring strain. Ordinary ethers do not react in the same manner. R-MgX C C H H H H + O oxirane (ethylene oxide) !" ! + R- CH 2 CH 2 O MgX !" ! + H 3 O + workup R- CH 2 CH 2 OH primary alcohol
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Examples CH 3 CHCH 2 CH 2 MgBr CH 3 + CH 2 -CH 2 O diethyl ether CH 3 CHCH 2 CH 2 CH 2 CH 2
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This note was uploaded on 07/22/2009 for the course CHEM 322AL taught by Professor Jung during the Summer '07 term at USC.

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Ch_322b_12.07 - Reactions of Organolithium and...

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