functional group pka - Department of Chemistry

Approximate pKa chart of the functional groups: values to know 1. Protonated carbonyl pKa = 7 Other important pKa s 2. Protonated alcohol or ether pKa = 2 to 3 H2 = 35 3. Carboxylic acid pKa = 4 5 4. Ammonium ion pKa = 9 10 5. Phenol pKa = 10 6. Thiol pKa = 10 7. Alcohol pKa = 16 18 8. Water pKa = 9. Amide pKa = 18 10. Alpha proton of ketone/aldehyde pKa = 20 11. Alpha proton of ester pKa = 25 12. Terminal alkyne pKa = 25 13. Amine pKa = 38 40 14. Aromatic: Aryl 43, benzylic 41 15. Alkene: vinyl 45 50; allylic 43 16. Alkane pKa = above 50 Examples: HHHHH(vinyl)(allylic)(aryl)(benzylic)NHH OHOOHNH2 OSHCH3 OOHH2 NOHOHOHOOH2above 50-7-2 to -3-2 to -34-59-10101016-181820252538-4041434345- 50

(aryl) (benzylic) N H H O H O OH NH2 O SH CH3 O OH H2 N OH OH O H O OH2 above 50-7-2 to -3 -2 to -3 4-5 9-10 10 10 16-18 18 20 25 25 38-40 41 43 43 45-50. Title: Microsoft Word - functional group pka Author: bburling Created Date:

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