Grignard Reagents and Other Functional Groups in the same molecule Can't be prepared if there are reactive functional groups in the same molecule, including proton donors MeX C—FG C—FG FG: OH. SH. NH. COH COH(R, OR, NH), CN, NO,, SO,R
Grignard Reagents and Other Functional Groups in the Same Molecule • Can't be prepared if there are reactive functional groups in the same molecule, including proton donors X C FG MgX C FG Mg FG: OH, SH, NH2 , CO2H; COH(R, OR, NH2 ), CN, NO2 , SO2R
8.6 Ethers from alcohols, The Williamson Ether Synthesis Reaction of metal alkoxides and primary alkyl halides and tosylates CH THF cH 0+1 solvent Cyclopentoxide ion Cyclopentyl methyl ether (74% ②2004 Thomson· Brooks/Cole ROH NaH RO Nat+ ho 2004 Thomson. Brooks/Cole
8.6 Ethers from Alcohols: The Williamson Ether Synthesis • Reaction of metal alkoxides and primary alkyl halides and tosylates
RⅩ ROH→RONa ROR or rots CH (CAlx CHX CHONa H3C-C-O-CH (CH3)3 CONa CH
ROH RONa R'X ROR' or R'OTs H3C C CH3 CH3 CH3ONa O CH3 (CH3 )3CONa (CH3 )3CX CH3X
299 Alkoxymercuration of Alkenes H OCH3 H OCHg H HgOoCCF H (CF3 CO2) Hg NaBh CHOH H HH HH Styrene 1- Methoxy. 1-phenylethane(97%) OCH, CH3 1.(CF: CO,)Hg, CHCH,OH Cyclohexene Cyclohexyl ethyl ether (100%) ②2004 Thomson· Brooks/Cole
Alkoxymercuration of Alkenes p.299
Silver Oxide-Catalyzedp502 Ether formation CHOO CHOOCH HO CHI CHO HO g2 CHO agl HO CHO OH OCH a-D-Glucose a-D-Glucose pentamethyl ether (85%) ②2004 Thomson· Brooks/Cole
Silver Oxide-Catalyzed Ether Formation p.502