Chapter Three

Chapter3:Acids&Ba#
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① Definitions
Bronsted Acid & Base
Lonny
• -

Conjugate acid & base

•

•
pKa values
•
reaction mechanism

② Concepts
•
How to predict / compare relative
acidity
I
-
& a

FEED ARILD
what are these ?
exactly

③ Applications
• How to apply fuse
either pKa valves
or ARIO to determine the

equilibrium of a rx n .

A + B CA + CB
Important notes to keep in mind while
we work
through this chapter :

If A is very stable
-

then HA
-

,
must be a
strong acid .

A unstable , then HA
-

-
if is
very
must be a weak acid .

-
The equilibrium of an acid base -

rxn
always favors the more stabilized
negative charge
* start here : Address important definitions

① Bron sled -

Lowry Acid & Base

•
An acid is a
proton donor
•
A base is a proton acceptor

t.it#.iaosei.-:isii:o;IEiiiF
② Conjugate Acid & Base
•
The products of a proton
transfer rxn are called CA & CB
-
CB is what remains of
the acid after deprotonation
-
CA is whet is
produced
after protonation

:÷÷÷+.÷÷÷:÷÷
 at this
Lets take a
quick look
quickly :

③ Reaction Mechanism

-
H Er + i : T t

if
-

*
"
u
,

•
All mins are accomplished via a

flow of electrons
density ( the motion

of electrons ) .

The flow of electron

•
density is

illustrated w/ cured arrows .

④ pKa valves
•
The rxn is said to have reached
equilibrium longer
when there is no

in the
an observable change
concentration of reactants 4 products

HA t Hz O F A
-

t Hz Ot

kegc.zos iaa-at.oy .gr

keg
[H30+][A][
-

HAT [ H2O ]

pKa =
log ka
¢
-
a
 In order to compare acids w/o the
use of pKa valves ,
we must look
at the conjugate base of each
acid :

If A is very stable
-

then HA
-

,
must be a
strong acid .

{
A unstable , then HA
-

-
if is
very
must be a weak acid .

I
TEETH is this """
%tTTm3
will give us another
way besides
determine the
pKa to where
equilibria
lies in a rxh

VARIO
① which atom bears the charge ?

④ Resonance ?

⑤ Induction ?

⑧ orbitals ?

But wait there's a catch : there are

exceptions to this method .
⑦ Atoms * The first factor involves
comparing
the bearing negative atoms the
in each CB
charge .

* In order to assess the relative

acidity of these two compounds ,
we first deep wtonele each
comports
& draw CB
in c . EN
OH

µ
N ~

de

~
pro
# ate

-0
. .
deptwtonate
~I
:-O Of
in c. size
which atom can deal w/ the
better ?
negativity
remember stable CB,
stronger
-
more

parent acid

④ Resonance* In order to assess the relative

acidity of these two compounds ,
we first deep wtonele each
comports
& draw CB
* Check for resonance (delocalization
of electrons )
 ~ IT
OH NO it
t d
deprotonate
deprotonete
O

H
T :O .
- :O
o .

charge
isteoceeized [ Io
Is
. )
o

remember stable CB,

stronger
-
more

parent acid

Induction
* In order to assess the relative
acidity of these two compounds ,
we first depwtonele each
comports
& draw CB
* Are there atoms that w/ draw
electron density via induction ?

o o
C' remember more
H II -

~ OH
c, # OH stable CB, the
the
L c '
stronger
& parent acid
deprotonated
deprotonated
d
O o
H Cl 11
No
-

a o
-

(I
⑧ Orbitals
* In order to assess the relative
acidity of these two compounds ,
we first deep wtonele each
comports
& draw CB
* Look at the
hybridization
States of the orbitals thet a ccomedek
the
chemo

deproton
ale
F- deprotomete

- -

¥
:X a
①

all these
techniques will help
you
determine which CB is more stable
in comparison This is important in
.

where the equilibrium

determining We will see this
in a rxh lies .

next . . .
 →

rt :

t.IE .
Nt
. in
.

Predict the position of equilibrium for rxh

2 TECHNIQUES
① Using pKa
①
Identify acid & CA
② pKa valves for each
Assign the

③ Arrow is drawn from

high to low #

?
~ + Nt i
. . .
. .
Base
Acid CA CB
P pka
→

⑤ Using ARLO

① Identify base & CB

② Determine which is more stable using

A- RIO

③ Draw arrow towards more stable

base

T.se?t .
.
.
Nt
.

CB
i
.