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acidity ladder

21 flashcardsby t

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1

alkanes (sp3 C-H)

50

2

alkenes (sp2 C=H)

45

3

amines (RNH2)

35

4

amides -- H on C (C=O N)

30

5

alkynes (sp C≡H)

25

6

nitrile (C≡N)

25

7

ester

25

8

ketone (=O)

~20

9

amides -- H attached to N (C=O + C-NH2)

~15

10

alcohols (O-H)

~16

11

phenol (aromatic O-H)

10

12

thiol (S-H)

10

13

ammonium ion (RNH3+)

10

14

cyanide (HCN)

10

15

nitro (NO2)

~10

16

carboxylic acid (RCO2H)

5

17

HF

3

18

H3O+

~-2

19

H2SO4

-10

20

HCl, HBr, HI

~-8, -9, -10

21

polarizability effect

↑size = ↓pKa

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