11 electrophilic aromatic substitution nitration 2011 SPRING corrected

11 electrophilic aromatic substitution nitration 2011 SPRING corrected

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Click to edit Master subtitle style 4/27/11 Electrophilic aromatic substitution Laboratory 8
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4/27/11 Behold the power of benzene Benzene’s aromaticity accounts for the resonance energy
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4/27/11 Electrophilic aromatic substitution H E + E H + R R R E E E ortho para meta
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4/27/11 Effect of substituents
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4/27/11 Nitration N O O O H S HO O O O H N O O O H H O N O -H 2 O Generation of electrophile O O O O NO 2 HNO 3 H 2 SO 4
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4/27/11 Mechanism O O O N O O O H N O O O O H N O O O O H N O O O O N O O -H + O O H N O O O O H N O O (+) (+) (+)
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4/27/11 Tips/procedure Ø Slowly add sulfuric acid to the nitric acid Ø Make sure all solutions are mixed very well Ø Do not leave thermometer in flasks or use thermometer to stir Ø Keep everything cold Ø Recrystallization – use minimum amount of solvent possible
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Splitting patterns in phenyl ring systems O O O 2 N O O O O NO 2 O 2 N H H H H o H m H p J = 6.5 – 8.5 Hz J = 1.0 – 3.0 Hz J = 0 – 1.0 Hz Often not observed How many unique H’s? O
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11 electrophilic aromatic substitution nitration 2011 SPRING corrected

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