lec7.pdf - Effects of Substituents on Electrophilic...

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Effects of Substituents on Electrophilic Aromatic Substitution Ortho-Para Directors Meta Directors Strongly Activating Moderately Deactivating -NH 2 -NHR -NR 2 -C≡N -OH -O - -SO 3 H Moderately Activating -CO 2 H -CO 2 R -NHCOCH 3 NHCOR -CHO -COR -OCH 3 -OR Strongly Deactivating Weakly Activating -NO 2 -CH 3 -C 2 H 5 -R -C 6 H 5 -NH 3 + -NR 3 + Weakly Deactivating -CF 3 -CCl 3 -F -Cl -Br -I Small contributors d - d - d - Most basic sites H H O H H H CH 3 H H O H H H H H O H H H H H O H H H CH 3 CH 3 CH 3 H H O H H H CH 3 H H CH 3 H H H H H CH 2 H H H H H H CH 2 H H H H H H CH 2 H H H H Very small contributors H H H H H CH 3 d - d - d - Most basic sites hyperconjugation ortho and para sites are the basic sites. Direct acid attack. CH 3 d - d - d - Most basic sites O d + d + d + Most basic sites Electron Donating Groups Electron Withdrawing Groups But less basic than benzene
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+ AlCl 3 AlCl 3 + AlCl 3 AlCl 3 Which of the following should be easiest to stop at the first product?
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