Aim To investigate the effect of chain length on the pH of weak

acids
ABSTRACT-----The aim on my investigation was to investigate the effect of chain length on the
PH of weak acids.
I investigated this by carrying out an acid-base titration on various carboxylic
acids such as methanoic acid and ethanoic acid in increasing carbon chain
lengths.
From this experiment I used the results to produce a scatter graph of PH. I used
this PH graph to work out the Pka values for each carboxylic acids. By working
out the Pka value from the graph I was able to see the effect of chain length on
the Ph on weak acid.
From my findings I could conclude that this matches/disagrees with the
principle: the smaller the pka value the stronger the acid is.
Introduction Hypothesis- I predict that as the carbon chain of the carboxylic acid increases the
pH of the acids decreases? Check with results etc
I choose to carry out my investigation testing carboxylic acids specifically as the
hydroxyl group in the compound gives this functional group its weakly acidic
properties. Carboxylic acid is a weak acid as the hydroxyl group in the compound
is different in strength in comparison to other compounds such as alcohols as it
can reversibly dissociate forming a hydrogen ion and a carboxylate ion. It is the
formation of these hydrogen ions in this dissociation that makes carboxylic acids
acidic.
pH tells you the concentration of hydrogen ions available in a solution therefore
the acidity. For example the higher the concentration of hydrogen ions there are
in a solution the lower the pH value and the stronger the acidity. Pka however is
more specific and tells you how a molecule will react; whether the molecule is
going to donate a proton or remove a proton. Knowing the pKa value is useful as
we will have a better understanding of the concentration of protons, as the more
protons there are the more acidic the solution will be.
Therefore the strengths of weak acids are measured on the pKa scale. pKa is a
simpler expression of Ka. The smaller the pKa value, the stronger the acid is.
The four compounds that will be looked at, together with their pKa values, are:
Compound
Methanoic acid
Ethanoic acid
Propanoic acid
Butanoic acid

Displayed formula
HCOOH
CH3COOH
CH3CH2COOH
CH3CH2CH2COOH

pKa
3.75 (strongest acid)
4.76
4.87
4.83 (weakest acid)

There is variation in acid strengths between different carboxylic acids. One

obvious difference is between methanoic acid, HCOOH, and the other simple
carboxylic acids:

pKa
HCOOH

3.75

CH3COOH

4.76

CH3CH2COOH

4.87

CH3CH2CH2COOH

4.83

Ethanoic acid is weaker than methanoic acid due to its stability of the anions
formed - on how much it is possible to delocalise the negative charge. The less
the charge is delocalised, the less stable the ion, and the weaker the acid.
The methanoate ion (from methanoic acid) is:

The only difference between this and the ethanoate ion is the presence of the
CH3 group in the ethanoate.
The presence of the CH3 alkyl group causes electrons to repel away from
themselves. Resulting in a small amount of extra negative charge built up on the
-COO-group. Any build-up of charge will make the ion less stable, and more
attractive to hydrogen ions. Ethanoic acid is therefore weaker than methanoic
acid, because it will re-form more easily from its ions.

The other alkyl groups have "electron-pushing" effects very similar to the methyl
group, and so the strengths of propanoic acid and butanoic acid are very similar
to ethanoic acid.
We can calculate the pH of a solution if we are given a pKa value or a Ka value
through the following equations:

Once the Ka value has been calculated using the given concentration of the
products and reactants we can work out the pH value:

If the pH of a solution equals the pKa, it denotes that it is half dissociated. If the
pH is less than the pKa value then it is mainly protonated acid; if the pH is more
than the pKa
value then it is
mainly
deprotonated.

Through use of acid-base titration, where a neutralisation reaction occurs, a

titration curve is formed for each carboxylic acid. Protons are transferred from
the acid to the base in an acid-base titration. From the titration curve, the
equivalence point is able to be obtained. This occurs when the quantity of
reagent added from the burrete (carboxylic acid) is the exact amount necessary
for stoichiometric reaction with the amount of reagent present in the conical
flask (sodium hydroxide)
The selection of a suitable indictor is vital in carrying out a titration. Indicators
are compounds that allow the identification of the end-point of titrations.
Commonly, a sudden colour change is visible when the titration is complete.
An acid-base titration is normally a weak organic acid that dissociates in aqueous
solution, as is the case in this investigation. Therefore, the following equilibrium
is established:

( aq)
+ + I n
HIn ( aq ) + H 2 O ( l ) H 3 O

In choosing an appropriate indicator, the type of acid-base reaction taking place

must be notes:
Acid-base reaction type
Strong acid / strong base
Strong acid / weak base
Weak acid / weak base
Weak acid / strong base

pH at equivalence point
7
<7
~7
>7

As seen by the highlighted acid base reaction of weak acid and strong base, an
indicator with a pH range above 7 is required.
Indicator

HIn colour

Phenolphthalein

Colourless

pH range of colour
change
8.3-10.0

In- colour
Pink

Phenolphthalein is the only suitable and available indicator for the weak acid
with strong base acid-base titration.

Procedure
Requirements

Sodium Hydroxide 1 mol-l

Methanoic Acid- state conc.
Ethanoic Acid- state conc
Pentanoic Acid- state conc
Butanoic Acid- state conc
100cm3 Conical flask- to accurate measurement of ..

50ml3 burette- A burette of 50 ml will be used to hold the

(acids) liquids during the experiment and to accurately
measure if the liquid is the volume I am measuring at
50cm3. A glass burette will be used for corrosive and
flammable liquids (such as.youll have to goggle if any are
corrosive etc) as it may cause a plastic burette to be
damaged.

25cm3 pipette- A pipette was used to..

250cm3 beakers- beakers will be used to hold each liquid when

being tested as its being let out from the burette this will
limit any spillages of the jet liquid.

Phenolphthalein indicator- was used to.

pH probe- was used to.,.

clamp stand- A clamp stand will be used to hold the burette

in position whilst carrying out the experiment this will limit
any spillages as the burette will be in a fixed position.

Hazcon
Wear eye protection and gloves if necessary. If any chemicals splashes on the
skin, wash it off immediately.
Change according to ur investigation.

Risk assessment and safety precautions:

Risk:

Level of Risk
-/10:

Who is at risk:

Control for risk:

Alcohol is a
corrosive
chemical

8 out of 10

Person
handling the
substance

Wear gloves to
ensure the skin is
not exposed to
corrosive
substances.

Person
handling
substance and
other people in
the room

Make sure all

liquids used in the
experiment are
carefully handled
when being
poured and if any
spillages occur
immediately clean
up as it may
cause slips or
trips.

Spillage of
substancessuch as water

Broken
glasswarematerial of the
spirit burner is
glass

5 out of 10

Carefully handle
glass material
such as beakers
and burettes
when moving
them and ensure
they are not kept
on the edge of the
table. If broken
place into broken
glassware box
with gloves.

9 out of 10

Person
handling
glassware

Flammable
substancesAlcohol

9 out of 10

Person
carrying out
experiment
and other
people in the
room

Make sure if the

spirit burner is
leaking it is kept
away from fire
source.

Trips and
injuries

5 out of 10

Person
travelling
around
laboratory

Make sure all

pathways of
laboratory are
clear when

Procedure
1. The 25cm3 pipette and 100cm3 conical flask were rinsed with a little of the
1 mol l-1 sodium hydroxide solution.
2. 25cm3 was then measured into the 100cm3 conical flask.
3. To this, two to three drops of Phenolphthalein were added.
4. The 50cm3 burette was rinsed with a little of the 1 mol l -1 methanoic acid
5. The burette was filled with methanoic acid
6. The methanoic acid was then titred into the sodium hydroxide with 2cm3
intervals. After, 2cm3 was added, the pH level of the sodium hydroxide
was recorded and noted. This was repeated until all the methanoic acid
was titred. When the neutralisation point was approaching, the volume
interval was lowered to 0.5cm3 at a time.
7. Steps 4 to 6 were repeated with the different carboxylic acid.
Burette
containing
carboxylic acid

Beaker
containing
NaOH (aq) and
Phenolphthalein

Controls and Duplications

All carboxylic acids were repeated three times with fresh chemicals each time.
This was to ensure none of the chemicals, especially sodium hydroxide, reacted
with anything else that could have off-set the results, as sodium hydroxide
readily absorbs moisture.
pH of all chemicals were tested before experiment was proceeded with to ensure
there was a level of control across the design of the investigation.
Accuracy of Measurement
The pH probe used to determine the pH of the solution was manufactured by
HANNA Instruments. This allowed for an accurate and reliable reading to be
taken due to the
When taking readings from the burette to 0.1 ml I ensured I used
meniscus readings each time at eye level to ensure the results taken
down with each experiment with each carboxylic acid were valid and
consistent.
Risk Assessment
The risks involved with sodium hydroxide can include severe irritation of the nose
and throat. Contact with sodium hydroxide can cause pain, redness, burns, and
blistering or even permanent scarring. Wearing of gloves is advised in conducting
this experiment. If gloves are not worn, if chemicals come in contact with skin,
they should be washed off immediately. If sodium hydroxide comes in contact
with eyes it can causes severe burns with redness, swelling, pain and blurred
vision. It could lead to permanent damage i.e. blinding. Therefore, safety goggles
should be worn at all times when dealing with sodium hydroxide.
Due to carboxylic acids being weak acids, the risks involved with the use of these
chemicals is less than that of sodium hydroxide but should still be taken into
consideration. As the concentrations of the chemicals are relatively low,
considerations such as harm in the eyes or in a cut must be noted.

Results
The recorded results for Methanoic acid are displayed in Table 1 and represented
in Graph 1.
volume
added

Average
pH

2
4
6
8
10
12
14
16
18
22.5
23
23.5
24

11
11
11
11
10.9
10.8
10.8
10.7
10.6
9.8
9.2
8.9
8.3

24.5
25
26
28
30
32
34
36
38
40
42
44
46
48

5.7
4.9
4
3.4
3.2
3
2.9
2.8
2.7
2.6
2.5
2.5
2.4
2.4

Methanoic Acid
12
10
8
pH

6
4
2
0

10

20

30

40

Volume of methanoic acid added

50

60

The results for Ethanoic Acid are shown in Table 2 and represented in Graph2.
Volume
added
0
2
4
6
8
10
12
14
16
18
20
22
24
24.5

Average
pH
11.6
11
11
11
10.9
10.9
10.8
10.8
10.7
10.6
10.6
10.3
8.1
5.6

25
25.5
26
28
30
32
34
36
38
40
42
44
46
48
50

5.2
4.9
4.7
4.4
4.2
4
4
3.9
3.9
3.7
3.6
3.6
3.6
3.6
3.5

Ethanoic acid
14
12
10
8
pH

6
4
2
0

10

20

30

40

Volume of ethaonic acid added

50

60

The results for Propanoic acid are shown in Table 3 and represented in Graph 3.
Volum
e
added

Avera
ge pH

0
2
4
6
8
10
12
14
16
18
20
22
24

11.2
11.2
11.1
11
11
11
10.9
10.9
10.9
10.8
10.8
10.7
10.7

26
28
30
32
34
36
38
40
42
44
46
48
50

10.6
10.5
10.4
10.3
9.8
7.9
5.1
4.8
4.5
4.4
4.3
4.3
4.1

Propanoic Acid
12
10
8
pH

6
4
2
0

10

20

30

40

Volume of propanoic acid added

50

60

The
butanoic
shown in
and

Volume
added
0
2
4
6
8
10
12
14
16
18
20
22
24
24.5

represented in Graph 4.

Average
pH
11.2
11
11
11
10.9
10.9
10.9
10.8
10.7
10.7
10.5
10.2
9
6.5

25
25.5
26
28
30
32
34
36
38
40
42
44
46
48

6
5.3
5
4.6
4.3
4.2
4
4
3.9
3.8
3.7
3.6
3.7
3.6

50

3.6

results for
acid are
Table 4

Butanoic Acid
12
10
8
pH

6
4
2
0

10

20

30

40

Volume of butanoic acid added

50

60

These titration curves show the variation in equivalence point between the
carboxylic acids. Analysis of the titration curve displayed in Graph 1 of Methanoic
acid, we can see

The pH of the solutions all depend on how easily the acids lose a
proton..
So factors that affect this are - electronegative substituents near the
carboxyl group these act to increase the acidity.
The presence of a carbonyl group adjacent to a hydroxyl group
have such a profound effect on the acidity of the hydroxyl proton
too. This is to do with the nature of acid-base equilibria and the
definition of pKa , illustrated by the general equations given below.

We know that an equilibrium favors the thermodynamically more

stable side, and that the magnitude of the equilibrium constant
reflects the energy difference between the components of each
side. In an acid base equilibrium the equilibrium always favors the
weaker acid and base (these are the more stable components).
Water is the standard base used for pKa measurements;
consequently, anything that stabilizes the conjugate base (A: ()) of
an acid will necessarily make that acid (HA) stronger and shift the
equilibrium to the right. Both the carboxyl group and the carboxylate
anion are stabilized by resonance, but the stabilization of the anion
is much greater than that of the neutral function).