Organic Chemistry I - Functional Groups & pKas

ether

R-O-R

Alcohol

R-OH

Carboxylic Acid

COOH

Ester

COOR

Acid Chlorine

-COCl

Amide

CONH2; Amine plus a keytone

Keytone

C=O

Amine

NH2

Sulfide

R-S-R

Thiol

R-SH

Aldehyde

CHO

alkane

Single bonded carbons

alkene

double bonded carbons

alkyne

triple bonded carbons

benzene ring (phenyl)

6-member ring with alternating double bonds.

Alkyl Halide

R-X (X being a halogen)

HCl pka

-7

TsOH, H2SO4 pka

-3

H3O+ pka

-2

H2O, alcohol pka

16

COOH (carboxylic acid) pKa

5

H2S pka

7

NH4 pka

9

Phenol (benzene + alcohol) pKa

10

aldehyde pKa

17

keytone pka

20

alkyne pKa

25

H2, NaH pKa

35

NH3 pka

38

alkene pka

44

Ch4, Me pka

50

ARIO

mnemonic for memorizing factors that affect the acidity of an acid. (Atom, Resonance, Induction, Orbital)

A in Ario

Atom; What atom is the acidic H attached to?

(i.e. atoms further down the periodic table will be more acidic)

R in Ario

Resonance; Is the conjugate base (deprotonated version) resonance stabilized?

I in Ario

Induction; Are there inductive effects from other atoms?

O in Ario

Orbital; how much s-character does the atom attached to the H have?

(i.e. HC-CH will have more s character than Me-Me)

ARIO is only useful when discussing _________ charges.

negative