ACID STRENGTH

2nd Group:

1. Umrotul Muna (4301414083)

2. Taufiq Hidayat (4301414084)

3. Sintia Ayu Dewi (4301414096)

4. Navela Rahma Aji (43014141089)

5. Siti Herlina D (4301414104)

6. Widya Rahmawati (4301414106)

ACID STRENGTH

ability of acid to release protons according to the definition of

Is
Arhenius and Bronsted Lowry.
HA H+ + A-
Based on experiment: acid strength depends on the solvent
Examples:
HCl + H2O H3O+ + Cl- strong acid
HCl + CH3COOH CH3COOH2 +
+ Cl- weak acid
 As if the solvent has the properties of increasing the acid strength
(leveling effect). So to determine the strength of acid, it used non
protonic solvent.
Example: benzene, ether, chloroform.
Acetic acid as a solvent has a great leveling effect on the base.
Example: ethyl amine in water: as a strong acid.
ethyl amine in acetic acid: as a strong base
HYDRO ACID
 Hydro acid
Acids where the proton bound directly on the central atom
Example : HF, HCl, HBr, HI

Hydroacid strength is determined by 2 factors:

1. The size of central atom
2. The electronegativity of central atom
The size of central atom
Increasingly the size of an atom, Then the strength its acid is more big
For a group of acids, the strength of acid determine by the size of central
atom
F, Cl, Br, I Increasingly the size of an atom, so the distance between
proten with central atom HF < HI, as a result the coulomb force /
electrostatic force of HI < HF. So HI is easier to release protons (HI is the
strongest acid)
The electronegativity of central atom
For acid which one period, the strength of acid determine by
electronegativity central atom CH4, NH3, H2O, HF electronegativity is
increasely
Polarity : HF > H2O > NH3 > CH4 so that the strength of acid HF > H2O >
NH3 > CH4
The electronegativity of central atom more big, so the strength of acid is
more big too
OXYACIDS
OXYACIDS

Oxyacid is an acid in which the proton is not attached directly to the central atom but
to the oxygen attached to the central atom. Examples: HOCl, HOCl2, HOCl3,
HOCl4.
 Acidity is determined by :

Central electronegativity
The higher the central atom electronegativity, the higher the ability of acid to
let proton. Because of the greater induction effect of the central atom to
attract electrons in the -OH bond.
Examples: HOH < HOI < HOBr < HOCl

Oxidation number of central atom

The higher the oxidation number of the central atom will increase the effect
of central atomic induction on the electron on the -OH bond.
Examples : HOCl < HOCl2 < HOCl3 < HOCl4.
Oxidation Number : +1 +3 +5 +7
 The size of central atom
The greater the size of the central atom will decrease the acidic
ability to release protons because the larger the central atom will
increase the tendency of the -OH release.
Example : HClO4 > HBrO4 > HIO4
Organic Acids
Definition

Organic acid is organic compound that has functional group of COOH

or OH
H from this functional group has protonic properties
The strength of this compound is strongly influenced by the groups that
are bondeb to those functional group
Factors that Determine Acid Strength
14
Anything that stabilizes a conjugate base A: makes the starting acid HA
more acidic.
Four factors affect the acidity of HA. These are:
Element effects
Inductive effects
Resonance effects
Hybridization effects
No matter which factor is discussed, the same procedure is always followed.
To compare the acidity of any two acids:
o Always draw the conjugate bases.
Determine which conjugate base is more stable.
The more stable the conjugate base, the more acidic the acid.
Element EffectsTrends in the Periodic Table.
15

Across a row of the periodic table, the acidity of HA increases as

the electronegativity of A increases.

Positive or negative charge is stabilized when it is spread over a larger

volume.
 Down
16 a column of the periodic table, the acidity of HA increases as the size
of A increases.

Size, and not electronegativity, determines acidity down a column.

The acidity of HA increases both left-to-right across a row and down a
column of the periodic table.
Although four factors determine the overall acidity of a particular hydrogen
atom, element effectsthe identity of Ais the single most important factor
in determining the acidity of the HA bond.
Factors that Determine Acid StrengthInductive Effects
17
An inductive effect is the pull of electron density through bonds caused by electronegativity
differ-ences between atoms.
In the example below, when we compare the acidities of ethanol and 2,2,2-trifluoroethanol,
we note that the latter is more acidic than the former.
 18 reason for the increased acidity of 2,2,2-trifluoroethanol is that the three electronegative
The
fluorine atoms stabilize the negatively charged conjugate base.
 When
19 electron density is pulled away from the negative charge through bonds
by very electronegative atoms, it is referred to as an electron withdrawing
inductive effect.
More electronegative atoms stabilize regions of high electron density by an
electron withdrawing inductive effect.
The more electronegative the atom and the closer it is to the site of the
negative charge, the greater the effect.
The acidity of HA increases with the presence of electron withdrawing groups
in A.
Factors that Determine Acid StrengthResonance Effects
20
Resonance is a third factor that influences acidity.
In the example below, when we compare the acidities of ethanol and acetic
acid, we note that the latter is more acidic than the former.

When the conjugate bases of the two species are compared, it is evident that
the conjugate base of acetic acid enjoys resonance stabilization, whereas that
of ethanol does not.
 Resonance delocalization makes CH3COO more stable than CH3CH2O, so CH3COOH is a
21
stronger acid than CH3CH2OH.

The acidity of HA increases when the conjugate base A: is resonance stabilized.

 22
Electrostatic potential plots of CH3CH2O and CH3COO below indicate that the negative
charge is concentrated on a single O in CH3CH2O, but delocalized over both of the O atoms
in CH3COO.
Factors that Determine Acid StrengthHybridization Effects
23
The final factor affecting the acidity of HA is the hybridization of A.

Let us consider the relative acidities of three different compounds containing CH bonds.

The higher the percent of s-character of the hybrid orbital, the closer the lone pair is held to the
nucleus, and the more stable the conjugate base.
24
 Figure 2.5
25
Summary of the factors that
determine acidity
Commonly
26 Used Acids in Organic Chemistry
In addition to the familiar acids HCl, H2SO4 and HNO3, a number of other acids are often used
in organic reactions. Two examples are acetic acid and p-toluene-sulfonic acid (TsOH).
Commonly Used Bases in Organic Chemistry
27
Common strong bases used in organic reactions are more varied in structure.
 It should be noted that:
28

Strong bases have weak conjugate acids with high pKa values, usually > 12.
Strong bases have a net negative charge, but not all negatively charged
species are strong bases. For example, none of the halides F, Cl, Br, or I, is
a strong base.
Carbanions, negatively charged carbon atoms, are especially strong bases. A
common example is butyllithium.
Two other weaker organic bases are triethylamine and pyridine.
Hard Soft Acid and Base
(HSAB)
Hard Soft Acid and Base (HSAB)

TheHSABconcept is an initialism for

"hardandsoft(Lewis)acidsandbases". Also
known as the Pearsonacid
baseconcept,HSABis widely used in chemistry
for explaining stability of compounds, reaction
mechanisms and pathways. It assigns the terms
'hard' or 'soft', and 'acid' or 'base' to chemical
species.
Acid: a compound that acts as an electron-pair
acceptor in the formation of a coordination
bond. Bases: a compound that is an electron-
pair donor in the formation of a coordination
bond.
Pearson in 1962: Metal ions in terms of Lewis
acid can be classified into two groups
 Class acid a: electron ion ions are poor
electrons such as alkali metal metals and
alkaline earth. Examples: Na+, Ba2+, Ca2+ etc.
Class B acids: relatively rich electron ion metal
ions are mainly transition metal metals /
heavy metal ions with low oxidation numbers.
Example: Cu2+, Cd2+, Ag+
 Cations have polarizing power properties: the ability of
a cation to polarize anions. The smaller the size, the
greater the payload the greater the polarizing power
Example: K+ < Ca2+
Anions have polarizability: the ability to experience
polarization. The larger the size, the larger the payload,
the greater the polarizability.
Example: O2- < S2-

Low polarizability ions are called hard ions

High polarizability ions are called soft ions
 Binding references:
Hard cations (hard acids) have perference with anions
(hard bases)
Hard cations (soft acid) have a perference with anions
(soft base)
Example: F-, Cl-, Br-. I- the more soft
Acid: Ag+ (hard acid_ then the tendency to bind
AgI> AgBr> AgCl> AgF
Then its solubility: AgI <AgBr <AgCl <AgF
THANK YOU
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