Chapter 22 lec note

Chapter 22 lec note - Chemistry 0320 - Spring 2008 Ch 22 -...

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Chemistry 0320 — Spring 2008 Ch 22 — Chemistry of Benzene Substituents page 1 Chapter 22: Chemistry of Benzene Substituents 22-1 Reactivity of The Benzylic Position Benzylic Radicals CH 3 toluene benzylic position (carbon) Br Br 2 , heat Mechanism Benzylic radicals are stable due to resonance:
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Chemistry 0320 — Spring 2008 Ch 22 — Chemistry of Benzene Substituents page 2 Benzylic Cations MeO OTs + EtOH S N 1 MeO OEt + TsOH Mechanism Why S N 1? Br Br + NaCN DMF CN + NaBr + NaCN DMF + NaBr CN faster slower S N 2 S N 2
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Chemistry 0320 — Spring 2008 Ch 22 — Chemistry of Benzene Substituents page 3 Benzylic Anions H H H pK a 41 40 50 22-2 Benzylic Oxidations and Reductions Oxidation KMnO 4 CO 2 H KMnO 4 CO 2 H KMnO 4 CO 2 H At least one benzylic C-H is required.
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Ch 22 — Chemistry of Benzene Substituents page 4 MnO 2 OH O MnO 2 OH O MnO 2 OH O MnO 2 only oxidizes allylic and benzylic alcohols. Reduction
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Chapter 22 lec note - Chemistry 0320 - Spring 2008 Ch 22 -...

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