Lecture 30 Phenols, Benzyne, SNAr (CN SYNTH)

Lecture 30 Phenols, Benzyne, SNAr (CN SYNTH) - O conc HI O...

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O conc HI Predict the products Chapter 21 O H Phenols and Aryl Halides: Nucleophilic Aromatic Subsitution O conc HI Predict the products OH I HO I i. ii. iii. iv A i + iii B i + iv C ii + iii D ii + iv O conc HI Predict the products OH I HO I i. ii. iii. iv A i + iii B i + iv C ii + iii D ii + iv Electrophilic Aromatic Substitution Phenols are very reactive OH OH thermodynamic Br 2 no catalyst needed Low Temp H 2 SO 4 100° OH Br HNO 3 dilute H 2 SO 4 25° SO 3 H OH OH 25 OH 100° H 2 SO 4 NO 2 + SO 3 H NO 2 30 - 40% 15% kinetic product Electrophilic Aromatic Substitution O H O NaOH OC O H + Kolbe Reaction very reactive O H O O H O O O + O H O O H O O H O O OH Predict the product H OH H O O O A B C D E Phenol can be oxidized to quinone OH H 2 CrO 4 O NaS 2 O 4 H 2 O OH O quinone Ag + OH hydroquinone
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Bombardier Beetle OH O OH H 2 O 2 O Shoots a stream of hot quinone The boiling solution is pulsed hyrdoquinone quinone 100° in shots of several hundred per second http://www.pnas.org/cgi/content/abstract/96/17/9705 http://www.youtube.com/watch?v=tpJ3as
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Lecture 30 Phenols, Benzyne, SNAr (CN SYNTH) - O conc HI O...

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