Alkyl Halides Organometallic Reagents 1) Grignard R X Mg0 + ether or THF reacts with: R MgII X H+, D+ electrophile (H2O, D2O) O now nucleophilic R 2 or R R H 6 HO 1 O 3 5 1 4 6 HO 2 5 3 4 disconnect between carbons 2 and 3 1 2 O MgBr + 6 MgBr 6 O 1 2 3 5 4 H2O 6 HO 1 2 3 5 4 3 5 4 2) Organolithium Li a) n-butyl lithium b) 2 H3C H3C Li + CuI ether H3C CuLi + LiI Formation H3C + CuLi H3C 2 1 I 2 ether 1 + LiI + CH3Cu Reaction any alkyl group Remember pKa of alkyl group is ~50 (very high) so deprotonated alkyl group is VERY basic H3C CH2 NaBr H2 H3C C Li very basic carbons will react w/ acidic proton like H2O (pKa 15.7) HC CH (pKa 25) Not mentioned in class: Chapter 10.10 Be familiar with terminology, oxidation, and reduction. In inorganic/general chemistry: (M=metal) M0 M2+ M2+ oxidation M0 reduction Organic chemistry: reduction: gain in electron density by carbon oxidation: loss of electron density by carbon In practice: oxidation C O C N C X bonds will form C X C H break reduction C H will form C O C N bonds will break A very common example: H2C CH2 Pd/C N2 H3C CH3 Reduction