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Introduction
Acidity and Basicity
Acids
 Anysolution that releases hydrogen ions
when added to water and has a pH of less
than 7.0
 pH – it measures the acidity of a liquid by
measuring the concentration of hydrogen ions.
PROPERTIES OF ACIDS :
 Sour taste

 Litmus paper blue turns red

 Reactions with metal oxide and hydroxide

 Neutralize bas forming water

Bases
 Substances which combines with acid
and also known as Alkaline substance.
 Compound that furnishes the hydroxide
ions.
 Compound that gives or donate hydroxyl
ions in water or other substances.

 Hydroxyl – unit that composed of one or

more atom of hydrogen and one of
oxygen.
PROPERTIES OF BASES :
 Slippery

 Soapy feeling and a biting , bitter taste

 Red litmus blue , turn methyl organic from

red to yellow

 Turn phenolphthalein from colorless to

red
Procedures
Acidity and Basicity
Using the pH Paper
pH paper Color Chart Record Repeat
in test • Match the • With other
solution color test solutions
obtained in
• Dip the test sol’n
• For 10
seconds
Using the pH Meter
Buffer First Solution Distilled Repeat
Solution • Dip the Water • With other test Keep the
• Immerse the electrode • Rinse the solutions
• Get the pH
electrode
electrode electrode
• After that, reading • Wipe it with
immersed in
rinse the • Record tissue paper distilled
electrode with water when
distilled water not inuse.
• Wipe with
tissue
Samples
 Chemical Structural Functional
Formula Formula Group

Carboxyclic
Acetic Acid CH3COOH
Acid

Carboxyclic
Monochloro-
ClCH2COOH Acid, Alkyl
acetic acid
Halides

Acetone (CH3)2CO Ketone

Acetamide CH3CONH2 Amides

 Chemical Structural Functional
Formula Formula Group

Amines,
Glysine NH2CH2COOH Carboxyxlic
Acid

Amines,
Carboxyxlic
Lysine C6H14N2O2
Acid

Isopropyl
(CH3)2CHOH Alcohol
Alcohol

Alcohol,
C6H5OH
Phenol Aromatic
Compound
 Chemical Formula Structural Formula

Commercial C2H4O2
Vinegar

Calamansi
C6H8O7
Juice

Spoiled Milk C3H6O3

Arrhenius
Concept
Acidity and Basicity
 Svante Arrhenius, a Swedish chemist who
received a Nobel prize in 1903 for his work
on electrolytes, focused on what ions
were formed when acids and bases
dissolved in water.
 One of the properties that acids and
bases have in common is that they are
electrolytes--they form ions when they
dissolve in water.
 He came up with the concept or idea
that acids dissociated in water to
give hydrogen ions (H+) and
that bases dissociated in water to give
hydroxide ions. (OH-)
Examples:
HCl  H+ + Cl-

An acid, like HCl, is something that

dissociates in water to give hydrogen ion.

NaOH H+ + Cl-

A base, like NaOH, is something that

dissociates in water to give hydroxide ion.
 Arrhenius focused on the idea that
acids and bases split into ions when
they dissolved in water.
 In a sense, the Arrhenius concept
focuses on what the chemical
contains or what is there in solution.
Brønsted-Lowry
Concept
Acidity and Basicity
 With the Brønsted-Lowry concept we
usually refer to a hydrogen ion as
a proton.
 That is because a proton is all that is left
when a hydrogen atom loses an electron
to become an ion.
Brønsted Acids
 Proton (H+) Donor.
 When an acid reacts, the proton
is transferred from one chemical to
another.
 The chemical which accepts the proton is
a base.
 H+ Cl- +

I DONATE!!

 + Cl-
Note that in order for an acid
to act like an acid, there needs
to be something for it to react
with. There needs to be
something to take the proton.

There needs to be a base.

Brønsted Bases
 Proton Acceptor.
 Opposite of acids.
 Bases are basic because they take or
accept protons.
 Hydroxide (OH-) ion, for example can
accept a proton to form water.
 Brønsted and Lowry realized that not all
bases had to have a hydroxide ion. As
long as something can accept a proton it
is a base.
 So anything, hydroxide or not, that can
accept a proton is a base under the
Brønsted-Lowry definition.
 The
water molecules that accept protons
when HCl dissolves in water are acting as
bases.

H Cl
+ - + I
ACCEPT!

I DONATE!

 + Cl-
 Some additional examples of Brønsted-
Lowry bases are shown accepting protons
in these equations. These examples do
not show the acids which are providing
the protons.
 Ammonia can accept or react with
hydrogen ion to give ammonium ion
(NH4+)

NH3 + H+  NH4+
 Carbonate ion (CO32- )can accept a
hydrogen ion, or accept a proton, to
become bicarbonate ion (HCO3-).

CO32- + H+  HCO3-

 Also,
water molecules, as mentioned
before, can act as a base by accepting
protons.

H2O + H+ H3O+
Hydroxide, ammonia, carbonate
and water are all Brønsted-Lowry
bases.
 When a Brønsted-Lowry acid donates a
proton, it forms the conjugate base of
that acid.
 When a base accepts a proton, it forms
the conjugate acid of that base.
 Conjugate base and acid are produced
as products.
 The formulas of a conjugate acid-base
pair differ by one proton (H+)
 Considerwhat happens when HCl(g) is bubbled
through water, as shown by this equation:

• The conjugate base of HCl is Cl-

• The conjugate acid of Cl- is HCl

Conjugate acid-base pair

HCl(g) + H2O(l) → Cl-(aq) + H3O+(aq)

Conjugate acid-base pair

• The conjugate base of H2O is H3O+

• The conjugate acid of H3O+ is H2O
 Towrite the conjugate base of an
acid,remove one proton from the acid
formula:
−H+
H2O OH- (Conjugate base)
−H+
HNO3 NO3- (Conjugate base)

 Notethat, by removing H+, the conjugate

base becomes more negative than the
acid by one minus charge.
 Towrite the conjugate acid of a base,
add one proton to the formula of the
base:

2-
+H+
SO4 HSO4- (Conjugate
acid)
+H+
C2H3O2- HC2H3O2 (Conjugate
acid)
 Ineach case the conjugate acid
becomes more positive than the base by
a +1 charge due to the addition of H+.
Lewis
Concept
Acidity and Basicity
The Lewis Concept as an
Extension of the Brønsted
Concept
 An acid is an electron-pair
acceptor.
 A base is an electron-pair donor.
 An acid-base reaction is the
sharing of an electron pair with an
acid by a base.
 These three simple definitions constitute the
heart of what is now known as the Lewis
concept of acids and bases.
 Experimentally and conceptually, they are
an extension of the Brønsted definitions.
The Fundamental Lewis Acid-
Base Reaction

 the formation of a coordinate covalent bond

between an acid and a base. The base is the
electron-pair donor, the acid the acceptor.
 The process is called neutralization, or simply
coordination.
 The product is a coordinated compound,
coordinated complex, or adduct, made up of
an acid portion and a base portion.
A typical, and oft-cited example is the
reaction of the acid boron trifluoride with
the base dimethyl ether to form the
complex or adduct BF3CH3OCH3:

 Thecoordinate molecule may be thought

of as being made up of the acid portion
BF3 and the base portion CH3OCH3
Classification of Lewis Acids
I. Simple Cations. Theoretically all simple cations
are potential Lewis Acids, although their
strength as acids varies within wide limits.
 In general, we can expect the acid strength
or coordinating ability of cations to increase
with:
 an increase in positive charge on the ion,
 an increase in nuclear charge for atoms in any
horizontal period,
 a decrease in ionic radius, and
 a decrease in the number of shielding electron
shells.
 Thismeans that Lewis acidity of simple
cations tends to increase for the elements
from left to right and from bottom to top in
the periodic table. (Periodic Trends)
II. Compounds Whose Central Atoms Has an
Incomplete Octet. Among the most
important Lewis Acids are compounds whose
central atom has less than a full octet of
electrons.
III. Compounds in Which the Octet of the
Central Atom Can be Expanded.

 Although carbon and silicon belong to

the same family of elements, silicon
tetrafluoride and silicon tetrachloride are
tremendously more reactive than their
carbon analogues, carbon tetrafluoride
and carbon tetrachloride.
 The explanation is straightforward- the
silicon, with its vacant d orbitals, can act as
a Lewis acid by expanding its octet.
 This is illustrated by the reaction of silicon
tetrafluoride with fluoride ion to form
fluorosilicate ion:
 With no available d orbitals, carbon
cannot do this, in keeping with the fact
that the elements in the first period of eight
in the periodic table can accommodate
no more than eight electrons in their
valence shell.
 Actually the silicon halides typify a large
group of halides which, with vacant d
orbitals, can expand their octets. Some
examples are:
 These halides tend to form adducts with
halide ions and with organic bases such as
ethers (R-O-R).
 Halides of this type are vigourously
hydrolyzed to form an oxy-acid (or oxide) of
the central atom and the appropriate
hydrogen halide. This reaction depends
upon the ability of the halides to act as Lewis
acids.
 The first step in the removal of each halogen
atom is undoubtedly the acid-base
coordination of the acid halide with the
base water. This is followed by elimination of
the hydrogen halide from the adduct.
 For the removal of the first chlorine in the
hydrolysis of phosphorus trichloride, we
believe the pathway or mechanism is
IV. Compounds Having Multiple-bonded Acid
Centres.

 Thereare many compounds, particularly

organic, in which a multiple-bonded atom
can accept a share in an electron pair with
a synchronous shift in a pair of electrons of
the multiple bond.
 By a slight extension of the Lewis concept,
we can classify such compounds as Lewis
acids. Although the atom involved does
not, in a strict sense, have an unfilled
orbital nevertheless an orbital is made
available as the incoming base forces the
intramolecular electron pair shift.
A familiar example is carbon dioxide.
Consider its neutralization by hydroxide ion to
hydrogen carbonate in:
V. Elements with an Electron Sextet.
 To the extent that oxygen and sulfur atoms
participate directly in chemical reactions,
they may be regarded as Lewis acids. On this
basis, the oxidation with sulfur of sulfite to
thiosulfate and of sulfide to polysulfide ion
can be classified as acid-base reactions:
Classification of Lewis Base
 They are species that contain atoms with lone
pairs. Such atoms are called donor atoms.
Thus H2O (donor atom, O), NH3 (donor atom,
N), Cl-, and CH3CH2OH (donor atoms, O) are
immediately recognized as Lewis bases.
 Because the number of Lewis bases is almost
unlimited, it is useful to categorize them based
on the number of donatable nonbonding
electron pairs that they contain.
 a Lewis base which can form only one
bond to a Lewis acid
name means
monodentate "one tooth"

has 2 or more
donor atoms spaced so that they can
attach to the same Lewis acid.
Normally the donor atoms must be
"spaced" non-linear,
by 2 or 3 intervening atoms. often with 2 or
chelating / 3 atoms
polydentate separating
the donor
atoms
Discussing the
Results
Acidity and Basicity
 pH Paper Reading pH Meter Reading
Acetic Acid 3 3.34
Monochloroacetic 1 1.96
acid

• Acetic Acid has a higher pH reading than

Monochloroacetic acid.

• But Monochloroacetic acid is more acidic than

Acetic acid.

Why is that so??

Acid Strength is influenced by
Inductive Effects

Carboxyclic acids are the

strongest acids among
compounds that contains only
C, H and O.
Acid Strength is influenced by
Inductive Effects
 Acetic acid provides the reference mark for a
typical carboxyclic acid and it has pKa value
of 4.75. The pKa value of monochloroacetic
acid is less than that for acetic acid.
Acid Strength is influenced by
Inductive Effects
 The variation in acidity among structurally
similar compounds like these can be
explained in the electronegativity values
of the substituents.
 These electronegativity difference
manifest themselves by donating or
withdrawing electrons through the bonds
between atoms, an influence known as
inductive effect.
Acid Strength is influenced by
Inductive Effects
 Inthe comparison of acetic and
monochloroacetic acids, the argument
goes like this:

“Chlorine, being electronegative, renders

the carbon atom adjacent to the carbonyl
group partially positive.”
Acid Strength is influenced by
Inductive Effects
 In turn, this withdraws electron density
from the carbonyl carbon atom and the
oxygen atom, bearing the proton.
 The effect is to weaken the O-H bond,
making the proton more acidic.
Acid Strength is influenced by
Inductive Effects
 Thus this inductive effect of the chlorine
atom makes monochloroacetic acid
more acidic than acetic acid.
 In general, an electron-withdrawing
substituent near the COOH group
increases the acidity of acetic acid.
Acid Strength is influenced by
Inductive Effects
 The more electronegative a substituent,
the stronger the acid.
 Conversely, an electron-donating
substituent makes the acid less acidic
than acetic acid.
 Alkyl groups are the most common
substituents that donate electrons.
 pH Paper Reading pH Meter Reading
Acetamide 9 8.19
Acetone 5 6.46

• Acetamide has a higher pH reading than

Acetone.

• Applying our basic information, pH less than 7

is acidic while pH more than 7 is basic. To
conlude, Acetamide is a base while Acetone is
an acid.

But what makes them a base and an acid?

Amphoteric character
(Amides)
 The presence of a lone pair of electrons
on Nitrogen atom should make acid
amide basic in character. But actually,
they are very feeble bases.
 This is because the lone pairs of electrons
on the nitrogen atom is involved in
Resonance with carbonyl group and is
therefore not available for protonation.
Amphoteric character
(Amides)

 However,under suitable conditions, acid

amide can show basic or acidic
character.
Amphoteric character
(Amides)

 The presence of lone pair of electrons on

the nitrogen atom is resonating structure
(I) makes it feebly basic.
 Acid amide, therefor, act as a base.
Amphoteric character
(Amides)
 Thus
acetamide (a base) reacts with
hydrochloric acid (an acid) to form a salt.
Amphoteric character
(Amides)
 Likewise,the positive charge on the
nitrogen atom shown in resonating
structure (II)

Implies easy release of proton.

Amphoteric character
(Amides)
 Acidamide, therefore, acts as an acid.
For example, acetamide behaving as an
acid reacts with bases Na or HgO to form
corresponding salt.
Acidity of Ketones
 Ketones are far more acidic (pKa ≈ 20)
than a regular alkane (pKa ≈ 50).
 This difference reflects resonance
stabilization of the enolate ion that is
formed through dissociation.
 The relative acidity of the α-hydrogen is
important in the enolization reactions of
ketones and other carbonyl compounds.
 The acidity of the α-hydrogen also allows
ketones and other carbonyl compounds
to undergo nucleophilic reactions at that
position, with either stoichiometric and
catalytic base.
 pH Paper Reading pH Meter Reading
Glycine 5 6.15
Lysine 6 6.17

• Glycine has a lower pH reading than Lysine.

• But Glycine is more acidic than Lysine.

Why is that so??

Chemical Nature of the Amino
Acids
 Theamino acids found in proteins have
the following generalized structure:
Chemical Nature of the Amino
Acids
 Allpeptides and polypeptides are
polymers of α-amino acids.
 Several other amino acids are found in
the body free or in combined states (i.e.
not associated with peptides or proteins).
Acid-Base Properties of the
Amino Acids
 The α-COOH and α-NH2 groups in amino
acids are capable of ionizing (as are the
acidic and basic R-groups of the amino
acids). As a result of their ionizability the
following ionic equilibrium reactions may
be written:
R-COOH <——> R-COO– + H+
R-NH3+ <——> R-NH2 + H+
 Theequilibrium reactions, as written,
demonstrate that amino acids contain at
least two weakly acidic groups.
 However, the carboxyl group is a far
stronger acid than the amino group. At
physiological pH (around 7.4) the
carboxyl group will be unprotonated and
the amino group will be protonated.
 An amino acid with no ionizable R-group
would be electrically neutral at this pH.
This species is termed a zwitterion.
 pH Paper Reading pH Meter Reading
Isopropyl Alcohol 4 3.40
Phenol 3 3.33

• Isopropyl Alcohol has a higher pH reading than

Phenol.

• But Phenol is more acidic than Isopropyl

Alcohol.

Why is that so??

Relative Acidities of Alcohols
and Phenols
 Thepolar O-H bond of alcohols makes
them weak acids. By the Bronsted-Lowry
definition, acids are hydrogen ion donors
and bases are hydrogen ion acceptors in
chemical reactions.
 Strong acids are 100% ionized in water
and weak acids are only partially ionized.
 Weak acids establish an equilibrium in
water between their ionized and
unionized forms.
 Phenolsare one million to one billion times
more acidic than alcohols and this is the
characteristic property that distinguishes
them. Phenols will react with the base
sodium hydroxide but alcohols will not.
 The acidity of phenols is explained by
resonance stabilization of the phenoxide
ion; the negative charge is dispersed
throughout the benzene ring as opposed
to being concentrated on the oxygen as
it is in the alkoxide ion.
 Electron-withdrawing groups on the
benzene ring increase the acidity of
phenols.
Chemical components that
makes it Acidic.
Spoiled Milk Lactic Acid C3H6O3

 Yes, spoiled milk is an acid.

 The lactic acid makes the milk acidic, milk
is said to be sour when it is at a pH level of
4.3-4.5 (acidic)
Chemical components that
makes it Acidic.
Citric Acid C6H8O7
Calamansi Juice
Ascorbic Acid C6H8O6

 Calamansi juice is an acid.

 It has mild sour taste.
 Sour taste is a characteristic of an acidic
property.
Chemical components that
makes it Acidic.
Acetic Acid
Commercial Vinegar CH3COOH
(Ethanoic acid)

 Acetic acid is the source of the acidity in

vinegar.
 Acetic acid (ethanoic acid) is an organic
acid (carboxylic acid) and is classified as
a weak acid.
Intramolecular H-Bond on
acidity
 Theeffects of intramolecular hydrogen
bonding on acidity can be see not just on
O-H and N-H, where acidity is greatly
reduced, but also on certain C-H groups,
which in some cases become the primary
source of acidity.