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Dolbier HW Solutions 286 - 280 REACTIONS OF ARENES...

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280 REACTIONS OF ARENES: ELECTROPHILIC AROMATIC SUBSTITUTION 12.3 The aromatic ring of 1,2,4,5-tetramethylbenzene has two equivalent hydrogen substituents. Sul- fonation of the ring leads to replacement of one of them by @ SO 3 H. 12.4 The major product is isopropylbenzene. Aluminum chloride coordinates with 1-chloropropane to give a Lewis acid/Lewis base complex, which can be attacked by benzene to yield propylbenzene or can undergo an intramolecular hydride shift to produce isopropyl cation. Isopropylbenzene arises by reaction of isopropyl cation with benzene. 12.5 The species that attacks the benzene ring is cyclohexyl cation, formed by protonation of cyclohexene. The mechanism for the reaction of cyclohexyl cation with benzene is analogous to the general mech- anism for electrophilic aromatic substitution. 12.6 The preparation of cyclohexylbenzene from cyclohexene and benzene was described in text Sec-
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