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Dolbier HW Solutions 271 - c Oxidation of the isopropyl...

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( c ) The structure portrayed for phenanthrene contains two terminal benzenoid rings and a non- benzenoid central ring. All three rings may be represented in benzenoid forms by converting one of the terminal six-membered rings to its alternative Kekul é form as shown: ( d ) Neither of the six-membered rings is benzenoid in the structure shown. By writing the cyclo- octatetraene portion of the molecule in its alternative representation, the two six-membered rings become benzenoid. 11.31 ( a ) Hydrogenation of isopropylbenzene converts the benzene ring to a cyclohexane unit. ( b ) Sodium and ethanol in liquid ammonia is the combination of reagents that brings about Birch reduction of benzene rings. The 1,4-cyclohexadiene that is formed has its isopropyl group as a substituent on one of the double bonds.
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Unformatted text preview: ( c ) Oxidation of the isopropyl side chain occurs. The benzene ring remains intact. ( d ) N-Bromosuccinimide is a reagent effective for the substitution of a benzylic hydrogen. CH(CH 3 ) 2 Isopropylbenzene 2-Bromo-2-phenylpropane N-Bromosuccinimide benzoyl peroxide, heat C CH 3 CH 3 Br CH(CH 3 ) 2 Isopropylbenzene Benzoic acid Na 2 Cr 2 O 7 , H 2 O H 2 SO 4 , heat COH O CH(CH 3 ) 2 1-Isopropyl-1,4-cyclohexadiene CH(CH 3 ) 2 Isopropylbenzene Na, ethanol NH 3 CH(CH 3 ) 2 Isopropylbenzene CH(CH 3 ) 2 Isopropylcyclohexane H 2 (3 mol) Pt Six-membered rings are not benzenoid. Six-membered rings are benzenoid. Central ring not benzenoid All three rings benzenoid ARENES AND AROMATICITY 265...
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