11 electrophilic aromatic substitution nitration 2011 SPRING corrected

11 electrophilic aromatic substitution nitration 2011 SPRING corrected

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4/27/11 1 Electrophilic aromatic substitution Laboratory 8 Behold the power of benzene Benzene’s aromaticity accounts for the resonance energy
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4/27/11 2 Electrophilic aromatic substitution ortho para meta Effect of substituents
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4/27/11 3 Nitration Generation of electrophile Mechanism
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4/27/11 4 Tips/procedure Slowly add sulfuric acid to the nitric acid Make sure all solutions are mixed very well Do not leave thermometer in flasks or use thermometer to stir Keep everything cold Recrystallization – use minimum amount of solvent possible Splitting patterns in phenyl ring systems 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?
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4/27/11 5 Signal one J ab = 1.0 - 3.0 Hz J ac = not observed J ad = 1.0 – 3.0 Hz H a is coupled to three non- equivalent protons: • This could give a a doublet of doublet of doublets [8 line pattern] • If J ab and J ad are similar, the resulting doublet signals might overlap to create a “triplet” with a
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11 electrophilic aromatic substitution nitration 2011 SPRING corrected

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