Transcription of ELECTROPHILIC AROMATIC SUBSTITUTION ... - Sapling …
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ELECTROPHILIC AROMATIC SUBSTITUTION ... - Sapling …
750 CHAPTER 16 THE CHEMISTRY OF BENZENE AND ITS DERIVATIVESThis hybridization allows one of its electron pairs to occupy a 2porbital, which has the samesize, shape, and orientation as the carbon 2porbitals of the ring. In other words, an oxygen 2porbital overlaps more effectively with the carbon 2porbitals of the ring than an oxygen sp3or-bital would. (We learned about the same effect in resonance-stabilized allylic systems; p. 713).The UV spectrum of anisole is a direct consequence of this (a) Explain why compound Ahas a UV spectrum with considerably greater lmaxvalues andintensities than are observed for ethylbenzene.
752 CHAPTER 16 • THE CHEMISTRY OF BENZENE AND ITS DERIVATIVES As you learned in Sec. 9.4F, LBr is a good leaving group. The fact that a much better leaving group than LBr is required for electrophilic aromatic substitution illustrates how unreactive
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