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Dolbier HW Solutions 293 - by attack of bromine on p-xylene...

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( h ) Anisole is a reactive substrate toward Friedel Crafts alkylation and yields a mixture of o - and p -benzylated products when treated with benzyl chloride and aluminum chloride. ( i ) Benzene will undergo acylation with benzoyl chloride and aluminum chloride. ( j ) A benzoyl substituent is meta-directing and deactivating. ( k ) Clemmensen reduction conditions involve treating a ketone with zinc amalgam and concen- trated hydrochloric acid. ( l ) Wolff Kishner reduction utilizes hydrazine, a base, and a high-boiling alcohol solvent to reduce ketone functions to methylene groups. 12.23 ( a ) There are three principal resonance forms of the cyclohexadienyl cation intermediate formed
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Unformatted text preview: by attack of bromine on p-xylene. CH 3 H Br CH 3 1 CH 3 CH 3 1 CH 3 CH 3 1 H Br H Br H 2 NNH 2 KOH diethylene glycol C O Benzophenone Diphenylmethane CH 2 Zn(Hg) HCl C O Benzophenone Diphenylmethane CH 2 HNO 3 H 2 SO 4 C O Benzophenone m-Nitrobenzophenone C O NO 2 AlCl 3 1 Benzene CCl O Benzoyl chloride C O Benzophenone AlCl 3 1 1 CH 2 Cl Benzyl chloride OCH 3 Anisole OCH 3 CH 2 C 6 H 5 o-Benzylanisole OCH 3 CH 2 C 6 H 5 p-Benzylanisole REACTIONS OF ARENES: ELECTROPHILIC AROMATIC SUBSTITUTION 287...
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