Ch_322b_20.16

Ch_322b_20.16 - The Hofmann Elimination Quaternary Ammonium...

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The Hofmann Elimination Quaternary Ammonium Salts Exhaustive N-alkylation converts amines into quaternary ammonium salts: Treatment of the quaternary ammonium halide with an aqueous solution of silver oxide (actually AgOH), precipitates AgX and yields a solution containing the quaternary ammonium hydroxide. RNH 2 primary R'X (-HX) RNH R' secondary R'X (-HX) RN-R' R' tertiary R'X (-HX) RN-R' R' R' + X - quaternary ammonium salt RN-R' R' R' + X - Ag 2 O H 2 O RN-R' R' R' + - OH quaternary ammonium hydroxide
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The Hofmann Elimination Treatment with aqueous silver oxide produces the hydroxide salt: In the late 19th century, the very prominent German-born chemist, August Wilhelm Hofmann (1818-1895) , discovered that the quaternary ammonium hydroxide salt undergoes an elimination reaction to produce an alkene upon heating. Hofmann made many important contributions to organic chemistry as a professor at the Royal College of Chemistry in London. In the traditional Hofmann elimination, a
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This note was uploaded on 10/20/2009 for the course CHEM 322BL at USC.

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Ch_322b_20.16 - The Hofmann Elimination Quaternary Ammonium...

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