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SCAN0004 - 1 RMgBr 2 H30 2 RH 2 H30 Alkyne 1 NaNHz 2 K or A...

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Unformatted text preview: 1) RMgBr 2) H30+ 2) RH 2) H30+ Alkyne 1) NaNHz 2) K or A 3) H30+ Examples: H H o H o+ O—MgCI + >20 (CZ—5h» CHZOMgCI ——‘°'—-——» CHZOH , H fl H; (C'Jt‘l‘iaéqfi formaldehyde primary alcohol Wt: it; 320 ~>I , I) . +H3 C ((32H5)2O H3O+ CH3(CH2)2LI )=0 -———> CH3(CH2)ZCHCH3 ———> CH3(CH2)2C!3HCH3 H I I aldehyde OH OH secondary alcohol C H ) 0 ON + _ HCEC‘Na+ + 0:0 (—3—5—5» H30 0 H CECH ketone tertiary alcohols 2) Addition to Ester 14.10, M, (T20.4), F14.2 l Organolithjum and iirignard reagents )react with esters to give tertiary alcohols. 1) RMgBr 2) H30+ 2) RLi 2) H30+ $72 moles of reagent are required per mole of W R 63 Ketovfl ———.» R—C-COCHg __. R-.._C }% CH3OMgBr I‘)® g—MgBr KWCDMIS this species is unstable and dissociates under the reaction conditions to form a ketone {365.5, R70‘ 06 % this ketone then goes on to react with a second mole of the Grignard reagent to give a tertiary alcohol M Example , S O t 1 diethyl ether 9H3 2 CH MgBr + CH CH—C E<OCH3 CH CH—C-OH 3 ( 3)2 ) 2. H30+ ( 3)2 (le T 3 \j 0045 Two of the groups attached to the '09 tertiary carbon come from the GrIgnard reagent Ll, ...
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