pka - H– SR H– + NR 3 H– C ≡ N H– OAr H– OC(O)R...

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5.12Fall2004 K.Berkowski Acidity of Organic Molecules Functional Group alkane- sp 3 alkene- 2 amine hydrogen alkyne- alcohol water thiol ammonium nitrile (cyanide) phenol carboxylic acid hydronium Acid Approximate p K a Values Conjugate Base increasing basicity CH 3 CH=CH 2 NH 2 H C CH OCR 3 OH SR NR 3 C N OAr OC(O)R F OH 2 Cl I (in water) 48 44 38 35 25 17 15.7 10–11 10–11 9.2 8–11 4–5 3.17 –1.74 –7 –10 H– CH 3 H– CH=CH 2 H– NH 2 H– H H– C CH H– OCR 3 H– OH
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Unformatted text preview: H– SR H– + NR 3 H– C ≡ N H– OAr H– OC(O)R H– F H– + OH 2 H– Cl H– I increasing acidity • Acidity increases across a row: H–C < H–N < H–O < H–F (electronegativity) • Acidity increases down a period: H–F < H–Cl < H–Br < H–I (size) • Neutral species less acidic than corresponding positively charged species: H–OH < H– + OH 2 p a data from: Advanced Organic Chemisry, 4th Ed., J. March...
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This note was uploaded on 04/27/2009 for the course CHM 231 taught by Professor Gust during the Spring '09 term at University of Arizona- Tucson.

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