Solutions_Manual_for_Organic_Chemistry_6th_Ed 432

Solutions_Manual_for_Organic_Chemistry_6th_Ed 432 -...

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Unformatted text preview: 1(a)8-59 BuLi CHz -PPh3O•O O CH2 lAenssexocycltihcandoublendocycli sic steable an e bond doubl bond. methylenecyclohexane (b) Then diffisciulnttyheinstsyntlhitesiofinthgemethyleenecyclionhexaneefromg cyclohexanone withoutsusientghethrienWit ig reactio irest abi y z doubl bond side th rin (endocyclic) versus out id g (exocycl c). HOoCH] : +. H20. + CH] MgBr major minor Aechanismiopassinlgowihroughe a dehydrat n fol t ng th m d carbocationitiuntteed,rmediate willdoubltehe Br t colCH3 give more subste majo product only bond asofthmakingrendocycl. icThec double o K+ -O-I-Bu chanceas the major tproduct is toi do an bondlimination usinhgeaexocyclbase to givee Hofmann orientatibulk(Cyhapter 7). on minor major 18-60 CI -CCHzCH2CH3 (a) • � zn(CIHg� � HV 0 (b) V C'N CH3CHzMgBr H3O+ V C-CH2CHl 1 .0 ether Cl OH OCH3 CI2 • 6 NaOH HC I) Na0,!;l 6 AlClI3• 1 0 AICI3 3500 C 6 CH31 .0 CuCI CHO 0:0:5 conc. H2SO: (d) HZCr207 I : I c6made 0�:> Alttehrnativelz,yt,htene cycldizchlobydFericould-Cberafts h wi aSOCIwith AICaci3I . ed ri edel acyl tion + E2 6 � El HB r + ° II ° E2 • ° II c5 6 + • � ( e) .0 2) co ¢l ° � • 427 ...
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