Dolbier HW Solutions 289

Dolbier HW Solutions 289 - 283 REACTIONS OF ARENES:...

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( c ) The acyl group in 1-phenyl-1-propanone is meta-directing; the carbonyl is attached directly to the ring. The product is 1-( m -nitrophenyl)-1-propanone. 12.15 Writing the structures out in more detail reveals that the substituent G 1 N(CH 3 ) 3 lacks the unshared electron pair of . This unshared pair is responsible for the powerful activating effect of an group. On the other hand, the nitrogen in G 1 N(CH 3 ) 3 is positively charged and in that respect resembles the nitro- gen of a nitro group. We expect the substituent G 1 N(CH 3 ) 3 to be deactivating and meta-directing. 12.16 The reaction is a Friedel Crafts alkylation in which 4-chlorobenzyl chloride serves as the carboca- tion source and chlorobenzene is the aromatic substrate. Alkylation occurs at the positions ortho and para to the chlorine substituent of chlorobenzene. 12.17 ( b ) Halogen substituents are ortho, para-directing, and the disposition in m -dichlorobenzene is such that their effects reinforce each other. The major product is 2,4-dichloro-1-nitrobenzene.
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