Acids and Bases

Lecture # 02
Brønsted–Lowry Acids and Bases
• The Brønsted–Lowry definition describes
acidity in terms of protons: positively
charged hydrogen ions, H+.

A Brønsted–Lowry acid must contain
a hydrogen atom. This definition of
an acid is often familiar, because
many inorganic acids in general
chemistry are Brønsted–Lowry acids.
The symbol H– A is used for a general
Brønsted–Lowry acid.
A Brønsted–Lowry base must be able
to form a bond to a proton. Because
a proton has no electrons, a base
must contain an “available” electron
pair that can be easily donated to
form a new bond. These include lone
pairs or electron pairs in π bonds.
The symbol B: is used for a general
Brønsted–Lowry base.
Examples of Brønsted–Lowry acids and bases
Compounds
• Compounds that contain both hydrogen
containing atoms and lone pairs may be either an acid
both H or a base, depending on the particular
reaction.
atoms and • Examples: H2O and CH3OH, Morphine etc.
lone pair
Morphine
• The addictive pain reliever morphine is
a Brønsted–Lowry acid because it
contains many hydrogen atoms.

• It is also a Brønsted–Lowry base because it

has lone pairs on O and N, and four π
bonds.
Reactions of Brønsted–Lowry Acids and Bases
• A Brønsted–Lowry acid–base reaction results in transfer of a proton from an acid to
a base.
• These acid–base reactions, also called proton transfer reactions, are fundamental to
the study of organic chemistry.

• Consider, for example, the reaction of the acid H –A with the base :B.
• In an acid–base reaction, one bond is broken and one is formed. The electron pair of the
base B: forms a new bond to the proton of the acid.
• The acid H – A loses a proton, leaving the electron pair in the H – A bond on A.
• Two products are formed.

Keep in mind two other facts about this general reaction:

The net charge must be the same on both sides of any equation. In this example, the
net charge on each side is zero.

A double reaction arrow is used between starting materials and products to indicate that the
reaction can proceed in the forward and reverse directions. These are equilibrium arrows.
Examples
 a. What is the
conjugate acid of
–
CH3O ?
Problems
b. What is the
conjugate base of
NH3?
Acid Strength and pKa
• Acid strength is the tendency of an acid to donate a proton.
 For most organic compounds, Ka
is small, typically 10–5 to 10–50.
This contrasts with the Ka values
for many inorganic acids, which

How is the range from 100 to 1010.

Because dealing with exponents can be cumbersome, it is often

magnitude of more convenient to use pKa values instead of Ka values.

Ka related to
acid strength?
Problems
• a. What is the pKa for each Ka:
10–10, 10–21

• b. Which compound is the stronger acid?

Factors That Determine Acid Strength

Four factors affect the acidity of H – A:

[1] Element effects: The acidity of H – A increases both left-to-right across a row and
down a column of the periodic table.
[2] Inductive effects: The acidity of H – A increases with the presence of electron-
withdrawing groups in A.
[3] Resonance effects: The acidity of H – A increases when the conjugate base A:– is
resonance stabilized.
[4] Hybridization effects: The acidity of H – A increases as the percent s-character of
the A:– increases.
Element effects
 Without reference to a pKa table,
decide which compound in each
pair is the stronger acid:
a. H2O or HF
Problems
b. H2S or H2O
Inductive Effects
Problem
• Which compound in each pair is the stronger acid?
• a. ClCH2COOH or FCH2COOH b. CH3COOH or O2NCH2COOH
Resonance Effects
Hybridization Effects
The final factor affecting the acidity of H – A is the hybridization of A.

To illustrate this phenomenon, compare ethane (CH3CH3), ethylene

(CH2––CH2), and acetylene (HC–CH), three different compounds
containing C – H bonds.
There is a considerable difference in the pKa values of these
compounds.
Problems
• For the following pair of compounds:
• [1] Which indicated H is more acidic?
• [2] Draw the conjugate base of each acid. [3] Which conjugate base is
stronger?
Summary of
the factors that
determine
acidity
Lewis Acids and
Bases
 Lewis Acids and Bases
• The Lewis definition of acids and bases is more general than the Brønsted–Lowry
definition.

Lewis bases are structurally the same as Brønsted–Lowry bases. Both have an
available electron pair—a lone pair or an electron pair in a π bond.

A Brønsted–Lowry base always donates this electron pair to a proton, but a

Lewis base donates this electron pair to anything that is electron deficient.
Examples of Lewis bases
• A Lewis acid must be able to accept an electron pair, but there are many ways for
this to occur.
• All Brønsted–Lowry acids are also Lewis acids, but the reverse is not necessarily
true.
• Common examples of Lewis acids (which are not Brønsted–Lowry acids) include BF3
and AlCl3.
• Any species that is electron deficient and capable of accepting an electron pair is
also a Lewis acid.
 Lewis acid–base reaction

• In a Lewis acid–base reaction, a Lewis base donates an electron pair to a Lewis acid. Most of the
reactions in organic chemistry involving movement of electron pairs can be classified as Lewis
acid–base reactions. Lewis acid–base reactions illustrate a general pattern of reactivity in organic
chemistry.

In the simplest Lewis acid–base reaction one bond is formed and no bonds are broken.
This is illustrated with the reaction of BF3 with H2O.

H2O donates an
electron pair to BF3
to form one new
bond.
In this Lewis acid–base reaction, BF3 is the electrophile and H2O is the nucleophile.

Other Examples
Problem
• For the following reaction, label the Lewis acid and base. Use curved
arrow notation to show the movement of electron pairs.
• In some Lewis acid–base reactions, one bond is formed and one bond is
broken.

• To draw the products of these reactions, keep the following steps in

mind.
✓[1] Always identify the Lewis acid and base first.
✓[2] Draw a curved arrow from the electron pair of the base to the
electron-deficient atom of the acid.
✓[3] Count electron pairs and break a bond when needed to keep the
correct number of valence electrons.
Example
References
1. Zuzana Országhová, Textbook of Medical Chemistry, 2018.
2. J. McMurry, Fundamental of Organic Chemistry, 7th edition.
3. J.G. Smith, Organic Chemistry, 3rd edition, 2010, McGraw Hill.