CHEM 203 + 213 - pKa values

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Hydrogen

36

Sulphric Acid

-3

Hydrochloric Acid

-8

Hydronium Cation and Protonated Alcohol

-2

Methanoic acid

4

Ethanoic Acid (CH3COOH)

5

XCH2COOH (X = F, Cl, or Br)

2.7

Alcohol and Water

16 (methanol 27 in DMSO)

Isopropyl-OH (2-propanol)

17 (29 in DMSO)

Tert butyl alcohol

18 (29 in DMSO)

Phenol

10

Protonated Carbonyl Group Z = H, C, OR, NH 2 , NHR, NR2

-6

Ammonium Cation (NH4+)

9

Protonated Amines

11

Amines

35

Diisopropylamine

38

Thiol (R-SH)

10

Alkane

50

Alkene

44

Alkyne (has lowest pKa because the most electronegative C at sp = C.B most stable)

25

Primary and Secondary Amide

15

Tertiary Amide

30

β-Diketone (R = carbon)/Dicarbonyl

9

β-Ketoester (R = carbon)

11 (+2)

Malonate Ester (R = carbon)

13 (+2)

Ketone 

22

Ester

25

Carbocation

-11

HBr

-9

HI

-10

Aldehyde

17

Cyclopentdiene

15

Vinyl

45

Imminium ion

4-5

Pyridinium (cation)

5

HCN

9

Nitroalkanes

10

Dinitriles

11

10 (Knoevenagel)