Acids and Bases

Arrhenius
Bronsted-Lowry
Lewis
 Definitions of Acids/Bases
+
Arrhenius acid - forms H 3O in H2O
-
Arrhenius base - forms OH in H2O
+
Bronsted-Lowry acid - donates a H (proton)
+
Bronsted-Lowry base - accepts a H (proton)

Lewis acid - accepts an electron pair to form a new bond

Lewis base - donates an electron pair to form a new bond
Measuring Acid Strength
Ka
Acid Strength defined by pKa
HCl + H2O H3O + Cl

[H3O ][Cl ]
Keq =
[HCl][H2O]
[H3O ][Cl ] 7
Ka = Keq[H2O] = = 10
[HCl]

pKa = -log(Ka) = -7
 Dissociation in H2O
Arrhenius Acid forms H3O+
Bronsted-Lowry Acid donates a H+
 Resonance Stabilization
H O
H O
H C C H
+ NaHCO3
O H C C
O
H
H
pKa 4.7
H2CO3 + Na
O 
H
Na H O
H C C
O  H C C
O
H
H
resonance hybrid
 Stronger Acid Controls
Equilibrium

HCl + H2O H3O + Cl

acid base conjugate conjugate
acid base
pKa = -7 -1.7
stronger weaker
Reaction Described with Arrows
HCl donates a proton
H2O accepts a proton

H
O
H Cl + O + Cl
H H
H H
Equilibrium Reactions
 Draw the Conjugate
Acid and Base

CH3CH2CH2OH + H2SO4
 Propanol is a Base

H
CH3CH2CH2OH + H2SO4 CH3CH2CH2OH
base acid
+ HSO4
 Draw the Conjugate
Acid and Base

CH3CH2CH2OH + Na NH2
 Propanol is an Acid

CH3CH2CH2O H + Na NH2 CH3CH2CH2O Na

acid base c.b.
+ NH3
c.a.
Some Acid-Base Reactions
The Effect of Resonance on pKa
 Identify the Acid and Base

O O
CH3OH + OCOH CH3O + HOCOH
 Equilibrium Favors Reactants
O O
CH3OH + OCOH CH3O + HOCOH

acid base conj. base conj. acid

pKa 15.5 6.5
 Carboxylic Acids can be
Separated from non-acidic
O
Compounds O
OCCH3 O OCCH3 O
C
C H O Na
O
+ Na OH
+ H2O
acid base conj. base conj. acid
Aspirin O
OCCH3 O Na
HCl C
O
 Lewis Acids and Bases

B H B H
base acid complex
arrow always goes from the base to the acid
always originate your arrow at the e- donor
 Formation of a new bond
H H

BH3 + NH3 H B N H
acid base
H H
complex

AlCl3
O O
CH3CH + AlCl3 CH3CH
base acid complex
Lewis Base = Nucleophile
Lewis Acid = Electrophile
Draw the Acid-Base Complexes

CH3OCH3 + FeCl3

+
CH3 + H2O

HOC(CH3)3 + AlCl3
 H H H
a) H
K H + C C C + H2
C
H C O H C O K
H H
H

O O
H
C H
C
b) CH3 C H O CH3 C H + H 2O
H H H
H

O O Li
Li H H
N
c) N
+ H +
 H H H
a) H
K H + C C C + H2
C
H C O H C O K
H H
H

O O
H
C H
C
b) CH3 C H O CH3 C H + H 2O
H H H
H

O O Li
Li H H
N
c) N
+ H +
 Draw Arrows
H H H H
a) H3N + C C C
H3N C
H C O H C O
H H

Br H H
b) CH3O H H C C + CH3OH + Br
C C H H CH3
H H
H H

Cl H CH3 CH3
c)
Cl B N BCl3 + HN
Cl CH3 CH3
 H H H H
a) C C C
H 3N H3N C
H C O H C O
H H

Br H H
b) CH3O H H C C + CH3OH + Br
C C H H CH3
H H
H H

Cl H
c)
Cl B N BCl3 + HN
Cl
 Identify the Conjugate Base
(i.e. Which H is most acidic?)

Ha O
H C H
e
Hb + Na NH2 NH3 + C6H7ONa
H Hd
Hc H
 Ha O
H C H
e
Hb + Na NH 2 NH3 + C6H7ONa
H Hd
Hc H By deprotonating one of the Hb protons, one can
distribute the charge onto three atoms and give a
major resonance structure with the charge on the
Oxygen (the third structure).
Ha O Ha O Ha O
C H H C H H C H
e b e e
Hb Hb
Hd Hd H Hd
H H
Hc H Hc H Hc H