Portmess Homework Q&S 118

Portmess Homework Q&S 118 - SO 4 140 145 C CO 2 H...

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( b ) Alkyl halides undergo E2 elimination on being heated with potassium tert -butoxide. ( c ) The exclusive product of this reaction is 1,2-dimethylcyclohexene. ( d ) Elimination can occur only in one direction, to give the alkene shown. ( e ) The reaction is a conventional one of alcohol dehydration and proceeds as written in 76 78% yield. ( f ) Dehydration of citric acid occurs, giving aconitic acid. ( g ) Sequential double dehydrohalogenation gives the diene. CH 3 Cl Cl H 3 C CH 3 KOC(CH 3 ) 3 DMSO KOC(CH 3 ) 3 DMSO Bornylene (83%) CH 3 Cl H 3 C CH 3 CH 3 H 3 C CH 3 OH CO 2 H CH 2 CO 2 H HO 2 CCH 2 C H 2
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Unformatted text preview: SO 4 140 145 C CO 2 H HO 2 CCH CCH 2 CO 2 H Citric acid Aconitic acid HO CH 3 O CN CH 3 O CN KHSO 4 130 150 C ( 2 H 2 O) (CH 3 ) 2 CCl KOC(CH 3 ) 3 (CH 3 ) 3 COH heat C H 2 C CH 3 NaOCH 2 CH 3 CH 3 CH 2 OH heat H CH 3 CH 3 CH 3 Br CH 3 1-Bromo-trans-1,2-dimethylcyclohexane 1,2-Dimethylcyclohexene (100%) KOC(CH 3 ) 3 (CH 3 ) 3 COH heat H 2 C C(OCH 2 CH 3 ) 2 ICH 2 CH(OCH 2 CH 3 ) 2 112 STRUCTURE AND PREPARATION OF ALKENES: ELIMINATION REACTIONS...
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