Acidity of Organic Molecules | Massachusetts Institute of Technology - Edubirdie

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Massachusetts Institute of Technology
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5.12 | Organic Chemistry I
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2023
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5.12 Fall 2004 K. Berkowski Acidity of Organic Molecules Functional Group Acid Approximate pKaValues (in water) Conjugate Base increasing basicity alkane-sp3 H–CH3 48 –CH alkene-sp2 H–CH=CH2 44 – H–NH2 38 – hydrogen H–H 35 – alkyne-sp H–C≡CH 25 –C≡CH alcohol H–OCR3 17 – – amine CH=CH2 NH 2 H OCR3 water H–OH 15.7 thiol H–SR 10–11 –SR ammonium H–+NR3 10–11 NR3 nitrile (cyanide) H–C≡N 9.2 phenol H–OAr 8–11 H–OC(O)R 4–5 – H–F 3.17 – H–+OH2 –1.74 carboxylic acid hydronium H–Cl –7 H–I –10 3 OH – C≡N –OAr OC(O)R F OH2 –Cl – 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–+OH2 pKa data from: Advanced Organic Chemisry, 4th Ed., J. March

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