Dolbier HW Solutions 248

Dolbier HW Solutions 248 - g The constitution of the Diels...

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( b ) Direct addition will occur according to Markovnikov s rule to give 3-chlorocyclohexene ( c ) The product of conjugate addition is 3-chlorocyclohexene also. Direct addition and conjugate addition of hydrogen chloride to 1,3-cyclohexadiene give the same product. ( d ) Bromine can add directly to one of the double bonds to give 3,4-dibromocyclohexene: ( e ) Conjugate addition of bromine will give 3,6-dibromocyclohexene: ( f ) Addition of 2 moles of bromine will yield 1,2,3,4-tetrabromocyclohexane.
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Unformatted text preview: ( g ) The constitution of the Diels – Alder adduct of 1,3-cyclohexadiene and maleic anhydride will have a bicyclo [2.2.2]octyl carbon skeleton. 1 O O O O O H H O 2Br 2 Br Br Br Br Br 2 conjugate addition Br Br 3,6-Dibromocyclohexene Br 2 direct addition Br Br 3,4-Dibromocyclohexene HCl conjugate addition Cl 3-Chlorocyclohexene HCl direct addition Cl 3-Chlorocyclohexene 242 CONJUGATION IN ALKADIENES AND ALLYLIC SYSTEMS...
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