Mindanao University of Science and Technology

C.M. Recto, Lapasan, Cagayan de Oro City

Structural Effects on Acidity and Basicity

Experiment 2

Presented by:
Allen Mark T. Librado
BS Chemistry

Presented to:
Mira Manatad

February 2015

I.

Introduction

Acids

and

bases

are

important

to

several

chemical

reactions. Acidity and basicity are one of many properties of

a

compound.

It

is

important

to

fully

grasp

what

sort

of

properties that contribute to its strength. When evaluating

acidity and basicity it is a must to look at the atom bearing
the proton/electron first. Such factors also need to consider
that affect the acidity and basicity of the compound like
resonance, inductive effect, the orbitals involved and the
charge of the atom.
In a simple reaction for the acidity, the more stable the
conjugate

base,

A-,

the

more

the

equilibrium

favors

the

product side. The more the equilibrium favors products, the

more H+ there is. The more H+ there is then the stronger H-A is
as an acid. So looking for factors like electronegativity,
size

and

resonance

that

stabilize

the

conjugate

base,

A -,

gives a tool for assessing acidity.

And a convenient way to look at basicity is based on the
availability

of

electron

pair.

The

more

available

the

electrons, the more readily it can be donated to form a new

bond to the proton and therefore the stronger the base.

There are a lot of ways to determine the acidity and

basicity of the compound. Few of the common apparatuses and
methods are pH meter and titration. As for this experiment,
few of the common compounds are studied by determing the pH
using a pH meter and how the structural effects affect acidity
and basicity of such compound.

II.

Methodology
A. Materials
pH meter
beaker
B. Samples
0.1 M phenol
95% Ethyl alcohol
1.1 M Acetic Acid
1.1 M Urea

C. Schematic Diagram
Sample

-Read pH using pH meter

pH values

III. Data

A. Table showing the different values of pH of samples using pH

meter.

SAMPLE

pH

0.1 M phenol
95% ethyl alcohol
0.1 M acetic acid
0.1 M urea

6.31
5.75
3.24
6.93

IV. Discussion

The most acidic of the four samples that was tested is

0.1 M acetic. 0.1 M phenol, 0.1 M urea and 95% ethyl alcohol

were

slightly

acidic.

Neutral

pH

is

7.0

but

none

exceed,

therefore, none of the sample were basic.

The structure of urea is,

If a proton (H+)

were extracted from one of the

the

resulting

urea

anion

nitrogen

would

not

be

atoms,

stabilized

by

delocalization, therefore, it is not acidic. The two nitrogen

atoms

of

available

urea
for

both

have

interactions

unpaired
with

electrons,

free

protons

which
as

are
base.

However, these unpaired electrons are not as basic as amines

because the carbonyl carbon already carries a partial positive
charge. But the two nitrogen are basic enough to make urea a
weak base. But generally, urea can neither be acidic nor basic
when dissolved in water.
Compounds like alcohols and phenol which contain an OH
group attached to a hydrocarbon are very weak acids. Alcohols
are

so

weakly

acidic

that

sometimes

their

acidity

are

virtually ignored. However, phenol is sufficiently acidic for

it to have a recognisably acidic properties, even if it is
still a very weak acid. A hydrogen ion can break away from the
OH group and transfer to a base. Phenol can lose a hydrogen
ion because of the phenoxide ion formed is stabilised to some
extent. The negative charge on the oxygen atom is delocalized
around the ring. One of the lone pairs on the oxygen atom

overlaps with the delocalized electrons on the benzene ring.

This overlap leads to a delocalization which extends from the
ring out over the oxygen atom. As a result, the negative
charge is no longer entirely localized on the oxygen, but is
spread out the whole ion. Spreading the charge around makes
the

ion

more

stable

than

it

would

be

if

all

the

charge

remained on the oxygen. That is why phenol is a very weak

acid.
Carboxylic acids like acetic acid are weak acids. When
dissolved in water they partially get associated into H + and
CH3COO- ions.
Some factors affecting the acidity of the compound based
on its structural design where the type of atom that is bonded
to the acidic hydrogen is considered. The more electronegative
the atom, the higher the possibility that it can get the
electron of the hydrogen which would then easily dissociate
into hydronium ion. Electronegativity applies across a period
but the size of the atom is prioritize when go down a group.
The bigger the size of the atom, the e asier the hydrogen atom
would dissociate because of the weakened bond between the two
atoms.

Second

is

hybridization.

The

orbital

energy

is

indirectly proportional to electronegativity. If the orbital

energy

is

low,

then

it

is

more

likely

to

form

bonding

attraction,

thus,

it

is

more

electronegative.

Increase

in

orbital electronegaivity means an increase in the acidity of

the compound. Third is Hydrogen bonding. High probability of
intramolecular H-bonding in a compound makes the compound more
acidic since it stabilizes the conjugate base of the compound.
Fourth is Inductive Effect. Electron withdrawing groups tend
to weaken the bond between a hydrogen and to where it is
bonded which makes it more acidic. Electron attracting groups
strngthens the bond between hydrogen and its partner which
makes it hard to leave its partner, thus, making them less
acidic.

Fifth

weakening

the

is

steric

bond

of

effect.
the

It

hydrogen

increases
or

acidity

decreasing

by
the

availability of the electron pair. It can decrease acidity by

decreasing ionization or increasing the availability of the
electron pair. Lastly, sixth is resonance. Generally, it is
said that it increases acidity due to the stabilization of the
conjugate base. In aromatic compounds, it increases acidity if
the attached group decreases the electron density of the ring.
It

decreases

acidity

if

the

electron density of the ring.

V.

Conclusion

attached

group

increases

the

It is important to know which factor will greatly affect

the acidity and basicity of the compound. With these factors,
one can know whether the compound is acidic or basic. As for
the compounds studied in this experiment, acetic acid is the
most acidic while phenol, ethyl alcohol and urea were slightly
acidic when used with pH meter. With the aid of pH meter, one
can quickly know whether the compound is acidic or basic. With
the knowledge on hybridization, hydrogen bonding, inductive
effect,

steric

effect

and

resonance,

one

can

be

able

to

identify if the given compound is an acid or base.

VI. References
http://www.chem.ucla.edu/harding/notes/notes_14C_str&react.pdf
http://www.chem.ucalgary.ca/courses/351/Carey5th/useful/acidba
se.html
http://www.chemistry2011.org/ResourceFiles/lecture02b_s05.pdf
https://www.ifm.liu.se/edu/chemistry/kurser/prep-org-kemi1/acids-and-bases.pdf
http://www.chem.ucalgary.ca/courses/350/Carey5th/Ch01/ch18.html