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EXPERIMENT # 11

ACIDITY & BASICITY

ORGANIC CHEM LAB.

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Acids & Bases Introduction

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ARRHENIUS CONCEPT
The earliest definition was given by Arrhenius:

•An acid contains a hydrogen atom and dissolves


in water to form a hydrogen ion, H+.

HCl(g) H+(aq) + Cl−(aq)


acid

•A base contains hydroxide and dissolves in water


to form −OH.

NaOH(s) Na+(aq) + −
OH(aq)
base
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LIMITATION OF ARRHENIUS CONCEPT

•It does not include many substances that behave


as acids and bases even in the gaseous phase
where no solvent is present, and those which
remains unionized in certain solvents like HCl in benzene,
liquid ammonia and amides such as sodium amide (NaNH2)

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BRONSTED- LOWRY CONCEPT

The Brønsted–Lowry definition is more widely used:

•A Brønsted–Lowry acid is a proton (H+) donor.


•A Brønsted–Lowry base is a proton (H+) acceptor.

This proton is donated.


HCl(g) + H2O(l) H3O+(aq) + Cl−(aq)

•HCl is a Brønsted–Lowry acid because it donates


a proton to the solvent water.
•H2O is a Brønsted–Lowry base because it accepts
a proton from HCl.
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Introduction to Acids and Bases
Brønsted–Lowry Acids
•A Brønsted–Lowry acid must contain a hydrogen
atom.
•Common Brønsted–Lowry acids (HA):

HCl H2SO4
hydrochloric acid sulfuric acid
H
HBr O acidic H
hydrobromic acid H C C atom

H O H
HNO3
nitric acid acetic acid
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Introduction to Acids and Bases
Brønsted–Lowry Acids
•A monoprotic acid contains one acidic proton.
HCl

•A diprotic acid contains two acidic protons.


H2SO4

•A triprotic acid contains three acidic protons.


H3PO4
•A Brønsted–Lowry acid may be neutral or it may
carry a net positive or negative charge.
HCl, H3O+, HSO4−
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Introduction to Acids and Bases
Brønsted–Lowry Bases

•A Brønsted–Lowry base is a proton acceptor,


so it must be able to form a bond to a proton.
•A base must contain a lone pair of electrons that
can be used to form a new bond to the proton.

This e− pair forms a new


bond to a H from H2O. H +

H N H + H2O(l) H N H + −
OH(aq)
H H
Brønsted–Lowry
base 8
Introduction to Acids and Bases
Brønsted–Lowry Bases
•Common Brønsted–Lowry Bases (B )
Lone pairs make these The −OH is the base in
neutral compounds bases. each metal salt.
NaOH
NH3
sodium hydroxide
ammonia
KOH
H2O potassium hydroxide
water Mg(OH)2
magnesium hydroxide
Ca(OH)2
calcium hydroxide 9
Proton Transfer
The Reaction of a Brønsted–Lowry Acid with
a Brønsted–Lowry Base

This e− pair forms


This e− pair a new bond to H+.
stays on A. gain of H+

H A + B A −
+ H B+
acid base

loss of H+

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Proton Transfer
The Reaction of a Brønsted–Lowry Acid with
a Brønsted–Lowry Base
gain of H+

H A + B A − + H B+
acid base conjugate conjugate
base acid

loss of H+
•The product formed by loss of a proton from an
acid is called its conjugate base.
•The product formed by gain of a proton by a base
is called its conjugate acid.
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Proton Transfer
The Reaction of a Brønsted–Lowry Acid with
a Brønsted–Lowry Base
gain of H+

H Br + H2O Br− + H3O+


acid base conjugate conjugate
base acid

loss of H+
•HBr and Br− are a conjugate acid–base pair.
•H2O and H3O+ are a conjugate acid–base pair.
•The net charge must be the same on both sides
of the equation. 12
Proton Transfer
The Reaction of a Brønsted–Lowry Acid with
a Brønsted–Lowry Base
•When a species gains a proton (H+), it gains a +1
charge.
H2O add H +
H3O+
base
zero charge +1 charge
•When a species loses a proton (H+), it effectively
gains a −1 charge.

HBr lose H+
Br−
acid
zero charge −1 charge 13
Proton Transfer
The Reaction of a Brønsted–Lowry Acid with
a Brønsted–Lowry Base
Amphoteric compound: A compound that contains
both a hydrogen atom and a lone pair of e−; it can
be either an acid or a base.
H +
add H+
H O H H O H
H2O as a base conjugate acid


remove H +
H O H H O
H2O as an acid conjugate base
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Acid and Base Strength
Relating Acid and Base Strength

•When a covalent acid dissolves in water, the proton


transfer that forms H3O+ is called dissociation.
•When a strong acid dissolves in water, 100% of
the acid dissociates into ions.

HCl(g) + H2O(l) H3O+(aq) + Cl−(aq)

•A single reaction arrow is used, because the


product is greatly favored at equilibrium.

•Common strong acids are HI, HBr, HCl, H2SO4,


and HNO3.
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Acid and Base Strength
Relating Acid and Base Strength
•When a weak acid dissolves in water, only a
small fraction of the acid dissociates into ions.

•Unequal reaction arrows are used, because the


reactants are usually favored at equilibrium.

CH3COOH(l) + H2O(l) H3O+(aq) + CH3COO−(aq)

•Common weak acids are H3PO4, HF, H2CO3, and


HCN.

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Acid and Base Strength
Relating Acid and Base Strength

A strong acid, HCl, is A weak acid contains


completely dissociated mostly undissociated
into H3O+(aq) and Cl−(aq). acid, CH3COOH.

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Acid and Base Strength
Relating Acid and Base Strength

•When a strong base dissolves in water, 100% of


the base dissociates into ions.

NaOH(s) + H2O(l) Na+(aq) + −


OH(aq)

•Common strong bases are NaOH and KOH.

•When a weak base dissolves in water, only a


small fraction of the base dissociates into ions.

NH3(g) + H2O(l) NH4+(aq) + −OH(aq)

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Acid and Base Strength
Relating Acid and Base Strength

A strong base, NaOH, is A weak base contains


completely dissociated mostly undissociated
into Na+(aq) and −OH(aq). base, NH3.
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Acid and Base Strength
Relating Acid and Base Strength

•A strong acid readily donates a proton, forming


a weak conjugate base.
HCl Cl−
strong acid weak conjugate base

•A strong base readily accepts a proton, forming


a weak conjugate acid.

OH H2O
strong base weak conjugate acid

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LEWIS ELECTRON- PAIR CONCEPT

•LEWIS ACIDS are defined as electron pair acceptors


•LEWIS BASES are electron pair donors

•A Lewis acids include all electrophilic (electron


seeking) or electron poor species,

• This extends weak the range of acid to chemical


species which have no hydrogen, those that possess
formal positive charges , and those with greatly
reduced electron densities .

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LEWIS ELECTRON- PAIR CONCEPT

•LEWIS ACIDS are defined as electron pair acceptors


•LEWIS BASES are electron pair donors

•A Lewis bases include all nucleophilic ( nucleus


seeking) or electron rich species.

•The range of Lewis bases is extended to those which


have excess negative charges

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The acidity or basicity of an aqueous solution expressed in terms
of the molar concentration of the hydrogen ion or hydroxide ion,
respectively.

• If the negative logarithm of the H+ concentration is taken,


a simple number called pH is obtained, thus for a Hydrogen ion
concentration of 1x10 -7 mole per liter the pH value is 7
(the pH of neutral solutions)

• Solutions with Hydrogen ion concentration greater than


1x10 -7 mole per liter (pH below 7) are acidic, and those with

• Hydrogen ion concentration lower than 1x10 -7mole per liter


(pH above 7) are basic or alkaline.

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The pH Scale
Calculating [H3O+] from pH

•If the pH of a solution is 8.50, what is the [H3O+]?


pH = −log [H3O+]

8.50 = −log [H3O+]

−8.50 = log [H3O+]

antilog (−8.50 ) = [H3O+]

[H3O+] = 3.2 x 10−9 M

•The solution is basic because [H3O+] > 1 x 10–7 M.


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Dissociation of Water

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The pH Scale
Calculating pH

pH = −log [H3O+]

The lower the pH, the higher the concentration of


H3O+.
•Acidic solution: pH < 7  [H3O+] > 1 x 10−7

•Neutral solution: pH = 7  [H3O+] = 1 x 10−7

•Basic solution: pH > 7  [H3O+] < 1 x 10−7

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The pH Scale
Calculating pH from [H3O+]

•If [H3O+] = 1.2 x 10–5 M for a solution, what is its pH?


pH = –log [H3O+] = –log (1.2 x 10–5)

= –(–4.92) = 4.92

•The solution is acidic because the pH < 7.

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The pH Scale
Calculating [H3O+] from pH

•If the pH of a solution is 8.50, what is the [H3O+]?


pH = −log [H3O+]

8.50 = −log [H3O+]

−8.50 = log [H3O+]

antilog (−8.50 ) = [H3O+]

[H3O+] = 3.2 x 10−9 M

•The solution is basic because [H3O+] > 1 x 10–7 M.


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The pH Scale
Calculating pH

•A logarithm has the same number of digits to the


right of the decimal point as are contained in the
coefficient of the original number.

[H3O+] = 3.2 x 10−9 M pH = 8.50

two significant two digits after


figures decimal point

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Focus on the Human Body
The pH of Body Fluids

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The Acidity and Basicity of Salt Solutions

Thus, the ion derived from the stronger acid or


base determines whether the solution is acidic
or basic.
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In the Laboratory the pH of a solution may be
measured approximately by using indicator
paper (pH paper) and more accurately by using a
pH meter

Objectives:
•To determine the pH value of different samples
with pH paper and pH meter
•To compare the results of the pH reading

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Procedure:
1. Determine the approximate pH of the different test
solutions using the pH paper.
a.Dip the piece of pH paper in the test solution for about
ten seconds. Remove the pH paper and place on a watch
glass.
b.Match the color produced in the pH paper with the color
chart to determine the ph of the solution
c.Record the results

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2. Determine the accurate pH of the tset solutions , using
the pH meter, by following these steps.

a. Immerse the electrode of the pH meter into the buffer


solution (standard)
b. Turn the knob to position the pH and check if the pointer
gives the correct reading of pH of the buffer solution as
standard. If the reading is not correct , turn the
standardization knob until the accurate reading is
obtained.
c. Remove the buffer solution , rinse the electrode with the
distilled water , and wipe dry with a tissue paper
d. Dip the electrode in to the first solution and turn the knob
to position pH . Get the reading on the scale and record.

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2. Determine the accurate pH of the tset solutions , using
the pH meter, by following these steps.

e. Turn back the knob to off position and remove the


electrode from the test solution.

f. Rinse the electrode with distilled water and wipe it dry.

g. Repeat the test with the other test solutions.

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Data & Observations
Test solutions pH paper reading pH meter reading
Acetic acid
Monochloroacetic acid
Acetamide
Acetone

Glycine
Lysine
Isopropyl alcohol
Phenol
Vinegar
Calamansi juice
Feminine wash 36
Data & Observations
Test solutions Structural Formula
Acetic acid CH3COOH
Monochloroacetic acid CH3COOCl
Acetamide CH3CONH2
Acetone CH3COCH3

Glycine NH2-CH2-COOH
Lysine NH2-CH- COOH
I
CH2CH2CH2CH2 NH2

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Data & Observations
Test solutions Structural Formula
Acetic acid CH3COOH
Monochloroacetic acid CH3COOCl
Acetamide CH3CONH2
Acetone CH3COCH3

Glycine NH2-CH2-COOH
Lysine NH2-CH- COOH
I
CH2CH2CH2CH2 NH2

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Data & Observations
Test solutions Structural Formula
Isopropyl alcohol CH3-CH-OH
I
CH3
Phenol C6H5-OH
Vinegar ( acetic acid) CH3-COOH
Calamansi juice (citric acid) C6H807
Feminine wash (lactic acid)

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TASK #1 Individual task

1. Review & differentiate the concepts of


acid and bases according to Arrhenius,
Bronsted –Lowry and Lewis.
(give example)

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Task #2. Answer by group.

2a. Research the pH value of the different test


solutions using pH meter reading (& pH paper reading
if any).

2b. Given the structural formula (slide 37-38) of the


test solutions, classify the test solutions as to acid,
base or neutral

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Task #3. Answer by group.

3. Answer the analysis and Interpretation


per group.
Reminders!
- Assign your Leader
-Assign question to your member
-Leader record in the data sheet who
answer the question

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Answers for task #1 & 2
can be send via gemina@ceu.gmail.com if you have a
good internet connections,
while data sheets (pp.55-56) will be
submitted on
May 4-6 , 2020 once classes are resume
God willing

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Class,
Be safe and keep praying
Thank you!
Dr. Mina

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