310-30 - CH 310 N LECTURE 30 Textbook Assignment: Chap 22...

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1 CH 310 N LECTURE 30 Textbook Assignment: Chap 22 Rxns of Benzene & Derivatives Homework (for credit): POW 10 posted (Due Apr 11) Today’s Topics: Rxns of Benzylic Position; EAS intro Notice & Announcements: 2 Benzene & Benzene & Aromaticity Aromaticity Chapter 21
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3 • Phenols are weak acids and react with strong bases to form water-soluble salts – water-insoluble phenols dissolve in NaOH(aq) OH NaOH O - Na + H 2 O Phenol p K a 9.95 (stronger acid) Sodium hydroxide Sodium phenoxide Water p K a 15.7 (weaker acid) ++ Acidity of Phenols Acidity of Phenols 4 –most phenols do not react with weak bases such as NaHCO 3 ; they do not dissolve in aqueous NaHCO 3 NaHCO 3 O - + H 2 CO 3 p K a 9.95 bicarbonate Carbonic acid p K a 6.36 Acidity of Phenols Acidity of Phenols
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5 Alkyl Alkyl -Aryl Ethers Aryl Ethers • Alkyl-aryl ethers can be prepared by the Williamson ether synthesis – but only using phenoxide salts and haloalkanes – haloarenes are unreactive to S N 2 reactions no reaction + X RO - Na + 6 OH CH 2 =CHCH 2 Cl NaOH, H 2 O, CH 2 2 Bu 4 N + Br - OCH 2 CH=CH 2 Phenyl 2-propenyl ether (Allyl phenyl ether) + Phenol 3-Chloropropene (Allyl chloride) O O 3 OSOCH 3 2 O, CH 2 2 4 N + - 3 2 SO 4 Methyl phenyl ether (Anisole) + Dimethyl sulfate + Alkyl Alkyl -Aryl Ethers Aryl Ethers
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This note was uploaded on 04/24/2011 for the course CH 56255 taught by Professor Colapret during the Spring '11 term at University of Texas at Austin.

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310-30 - CH 310 N LECTURE 30 Textbook Assignment: Chap 22...

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