Lecture Lab B - Aromatic Substitution Recrystallization and...

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Aromatic Substitution Recrystallization and mixed melting points February 6, 2009
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Electrophilic Aromatic Substitution Br 2 Br 2 + rapid reaction, loss of orange color + NO REACTION A stronger electrophile than Br 2 is required to disrupt aromaticity
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Iodination of durene Use a better electrophile I + I 2 I HIO 4 . 2H 2 O H 2 SO 4 aq HOAc
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Formation of strong electrophile I 2 + IO 4 - → I + + H 2 O (unbalanced) Oxidation States: I 2 IO 4 - I + Oxidized reducing agent Reduced Oxidizing agent Usually I 2 is an oxidant, and is reduced to I -
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Balancing the equation I 2 I + + e - IO 4 - I + e - + I 2 + IO 4 - → I + +
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The overall equation I + I + + H +
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Mechanism
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What is in solution when the reaction is 50% complete? Unreacted durene Iododurene product • I + , HIO 4 , I 2 , water, acid mixture
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Will additional reaction occur? Is the starting material or the product more reactive? Compare the relative energies of the first intermediates I H I H I
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Equivalents and stoichiometry Equivalents are the EXPERIMENTAL ratio in which reagents are added Stoichiometry is the mole ratio in which reagents react (from the balanced equation) Take into consideration stoichiometry when determining the percent yield!
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This note was uploaded on 03/24/2009 for the course CHEMISTRY 030.225 taught by Professor Janegreco during the Spring '09 term at Johns Hopkins.

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Lecture Lab B - Aromatic Substitution Recrystallization and...

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