Dolbier HW Solutions 290

Dolbier HW Solutions 290 - 284 REACTIONS OF ARENES:...

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( d ) A methoxy group is ortho, para-directing, and a carbonyl group is meta-directing. The open positions of the ring that are activated by the methoxy group in p -methoxyacetophenone are also those that are meta to the carbonyl, so the directing effects of the two substituents reinforce each other. Nitration of p -methoxyacetophenone yields 4-methoxy-3-nitroacetophenone. ( e ) The methoxy group of p -methylanisole activates the positions that are ortho to it; the methyl activates those ortho to itself. Methoxy is a more powerful activating substituent than methyl, so nitration occurs ortho to the methoxy group. ( f ) All the substituents in 2,6-dibromoanisole are ortho, para-directing, and their effects are felt at different positions. The methoxy group, however, is a far more powerful activating substituent than bromine, so it controls the regioselectivity of nitration. 12.18 The product that is obtained when benzene is subjected to bromination and nitration depends on the order in which the reactions are carried out. A nitro group is meta-directing, and so if it is introduced
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This note was uploaded on 09/26/2011 for the course CHM 2210 taught by Professor Reynolds during the Fall '01 term at University of Florida.

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