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electrophilicaromaticsubstitution

electrophilicaromaticsubstitution - Electrophilic Aromatic...

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Electrophilic Aromatic Substitution (Aromatic compounds) Ar-H = aromatic compound 1. Nitration Ar-H + HNO 3 , H 2 SO 4 Ar-NO 2 + H 2 O 2. Sulfonation Ar-H + H 2 SO 4 , SO 3 Ar-SO 3 H + H 2 O 3. Halogenation Ar-H + X 2 , Fe Ar-X + HX 4. Friedel-Crafts alkylation Ar-H + R-X, AlCl 3 Ar-R + HX
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Friedel-Crafts alkylation (variations) a) Ar-H + R-X, AlCl 3 Ar-R + HX b) Ar-H + R-OH, H + Ar-R + H 2 O c) Ar-H + Alkene, H + Ar-R
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NO 2 SO 3 H Br CH 2 CH 3 HNO 3 H 2 SO 4 SO 3 H 2 SO 4 Br 2 , Fe CH 3 CH 2 -Br AlCl 3
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toluene CH 3 CH 3 CH 3 CH 3 CH 3 CH 3 CH 3 CH 3 CH 3 Br Br NO 2 NO 2 SO 3 H SO 3 H HNO 3 H 2 SO 4 SO 3 H 2 SO 4 Br 2 , Fe + + + faster than the same reactions with benzene
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nitrobenzene NO 2 NO 2 NO 2 NO 2 NO 2 NO 2 NO 2 SO 3 H Cl HNO 3 H 2 SO 4 H 2 SO 4 SO 3 Cl 2 , Fe slower than the same reactions with benzene
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Substituent groups on a benzene ring affect electrophilic aromatic substitution reactions in two ways: 1) reactivity activate (faster than benzene) or deactivate (slower than benzene) 2) orientation ortho- + para- direction or meta- direction
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-CH 3 activates the benzene ring towards EAS directs substitution to the ortho- & para- positions -NO 2 deactivates the benzene ring towards EAS directs substitution to the meta - position
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Common substituent groups and their effect on EAS: -NH 2 , -NHR, -NR 2 -OH -OR -NHCOCH 3 -C 6 H 5 -R -H -X -CHO, -COR -SO 3 H -COOH, -COOR -CN -NR 3 + -NO 2 increasing reactivity ortho/para directors meta directors
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OCH 3 CHO Br Br 2 , Fe HNO 3 , H 2 SO 4 H 2 SO 4 , SO 3 OCH 3 Br OCH 3 Br + faster than benzene CHO NO 2 slower than benzene + Br Br SO 3 H SO 3 H slower than benzene
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If there is more than one group on the benzene ring: 1. The group that is more activating (higher on “the list”) will direct the next substitution. 2. You will get little or no substitution between groups that are meta - to each other.
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CH 3 OH NHCOCH 3 CH 3 CHO OCH 3 Br 2 , Fe HNO 3 , H 2 SO 4 Cl 2 , Fe CH 3 OH Br NHCOCH 3 CH 3 NO 2 CHO OCH 3 Cl CHO OCH 3 Cl +
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Orientation and synthesis .
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