Chapter 3
Acids and Bases
Review of Concepts
Fill in the blanks below. To verify that your answers are correct, look in your textbook at the end of
Chapter 3. Each of the sentences below appears verbatim in the section entitled Review of Concepts and
Vocabulary.
donor while a Brønsted-Lowry base is a proton
A Brønsted-Lowry acid is a proton ________,
acceptor
_____________.
electrons
A reaction mechanism utilizes curved arrows to show the flow of _____________ that account
for a chemical reaction.
two curved arrows.
The mechanism of proton transfer always involves at least _____
low
A strong acid has a ________ high
pKa, while a weak acid has a _________ pKa.
stability
There are four factors to consider when comparing the ___________ of anionic conjugate bases.
stable
The equilibrium of an acid-base reaction always favors the more ____________ negative charge.
acceptor
A Lewis acid is an electron-pair ___________, donor
while a Lewis base is an electron-pair _________.
Review of Skills
Fill in the blanks and empty boxes below. To verify that your answers are correct, look in your textbook at
the end of Chapter 3. The answers appear in the section entitled SkillBuilder Review.
SkillBuilder 3.1 Drawing the Mechanism of a Proton Transfer
SkillBuilder 3.2 Using pKa Values to Compare Acids
Circle the compound below that is more acidic:
O O
OH
pKa = 19.2 pKa = 4.75
SkillBuilder 3.3 Using pKa Values to Compare Basicity
70 CHAPTER 3
SkillBuilder 3.4 Using pKa Values to Predict the Position of Equilibrium
SkillBuilder 3.5 Assessing Relative Stability. Factor 1 – Atom
SkillBuilder 3.6 Assessing Relative Stability. Factor 2 – Resonance
SkillBuilder 3.7 Assessing Relative Stability. Factor 3 – Induction
SkillBuilder 3.8 Assessing Relative Stability. Factor 4 – Orbital
SkillBuilder 3.9 Assessing Relative Stability. Using All Four Factors
SkillBuilder 3.10 Assessing the Relative Acidity of Cationic Acids
SkillBuilder 3.11 Predicting the Position of Equilibrium Without Using pKa Values
CHAPTER 3 71
SkillBuilder 3.12 Choosing the Appropriate Reagent for a Proton Transfer Reaction
SkillBuilder 3.13 Identifying Lewis Acids and Lewis Bases
Common Mistakes to Avoid
When drawing the mechanism of a proton transfer, two curved arrows are required. The first curved arrow
shows the base attacking the proton, and the second curved arrow shows the bond to H being broken.
It is a common mistake to draw only the first curved arrow and not the second, so make sure to draw both
curved arrows. When drawing the second curved arrow, make sure that the tail is placed on the middle of
the bond to the H, as shown:
When the acid is H3O+, you must draw at least one of the O–H bonds in order to draw the second curved
arrow properly.
This is also the case for other acids:
72 CHAPTER 3
Useful reagents
In Chapter 3, we explored the behavior of acids and bases. Throughout the remainder of the textbook,
many acids and bases will be frequently encountered. It would be wise to become familiar with the
following reagents (and their uses), as they will appear many times in the upcoming chapters:
Structure Name Use
A very strong acid. Commonly used as a source of protons.
O Concentrated sulfuric acid is a mixture of H2SO4 and H2O,
and the acid present in solution is actually H3O+, because of
H O S OH Sulfuric acid
the leveling effect. That is, H3O+ is a weaker acid than
O H2SO4, so the protons are transferred from H2SO4 to water,
giving a high concentration of H3O+.
A very strong acid. Similar in function to H2SO4. In an
Hydrochloric
aqueous solution of HCl, the acid that is present is H3O+,
acid
because of the leveling effect, as described above for H2SO4.
Acetic acid A weak acid. Mild source of protons.
A weak acid and a weak base. It can function as either,
depending on the conditions. When treated with a strong
Water base, water will function as an acid (a source of protons).
When treated with a strong acid, water will function as a
base and remove a proton from the strong acid.
R represents the rest of the compound. Alcohols (the subject
of Chapter 12) are compounds that possess an OH group
An alcohol connected to an sp3-hybridized carbon atom. Alcohols can
function very much like water (either as weak acids or as
weak bases).
A fairly strong base, despite the absence of a negative
Ammonia charge. It is a strong base, because its conjugate acid
(NH4+), called an ammonium ion, is a weak acid (pKa = 9.2).
The ethoxide ion (CH3CH2Oˉ) is a strong base, and Na+ is
the counterion. Other alkoxide ions (ROˉ, where R is an
CH3CH2ONa Sodium ethoxide
alkyl group), such as methoxide (CH3Oˉ), are also strong
bases.
NaNH2 Sodium amide H2Nˉ is a very strong base, and Na+ is the counterion.
An extremely strong base. This is one of the strongest bases
n-Butyllithium
that you will encounter. It is often abbreviated as n-BuLi