Chapter 3

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Section 3.1

1. In the following acid-base reaction, the indicated molecule is

functioning as a(n)  ___ ?

 a. Acid

 b. Base

 c. Conjugate acid

 d. Conjugate base

Answer: b

Acids donate or lose a hydrogen ion (proton). Bases accept or

gain a proton. Acids and bases by convention are located on the
left side of the reaction arrows. Conjugate acids are the bases
after they have accepted/added a proton. Conjugate bases are
the acids after they have donated/removed a proton. Conjugate
acids and bases by convention are located on the right side of
the reaction arrows. In this reaction, the pyridine accepts a
hydrogen from the butanoic acid; therefore it is a base. For more
examples of this type of problem, see Skillbuilder 3.1.
Section: 3.1

2. In the following acid-base reaction, the indicated molecule is

functioning as a(n)  ___ ?

 a. Acid

 b. Base

 c. Conjugate acid

 d. Conjugate base

Answer: a

Acids donate or lose a hydrogen ion (proton). Bases accept or

gain a proton. Acids and bases by convention are located on the
left side of the reaction arrows. Conjugate acids are the bases
after they have accepted/added a proton. Conjugate bases are the
acids after they have donated/removed a proton. Conjugate acids
and bases by convention are located on the right side of the
reaction arrows. In this reaction, the butanoic acid donates a
proton to the pyridine; therefore it is an acid. For more examples
of this type of problem, see Skillbuilder 3.1.
Section: 3.1

3. In the following acid-base reaction, the indicated molecule is

functioning as a(n)  ___ ?

 a. Acid

 b. Base

 c. Conjugate acid

 d. Conjugate base

Answer : c

Acids donate or lose a hydrogen ion (proton). Bases accept or

gain a proton. Acids and bases by convention are located on the
left side of the reaction arrows. Conjugate acids are the bases
after they have accepted/added a proton. Conjugate bases are the
acids after they have donated/removed a proton. Conjugate acids
and bases by convention are located on the right side of the
reaction arrows. In this reaction, the pyridine has accepted a
proton from the butanoic acid to become protonated. The
protonated pyridine can now donate a proton and has become the
conjugate acid. For more examples of this type of problem, see
Skillbuilder 3.1.
Section: 3.1

4. In the following acid-base reaction, the indicated molecule is

functioning as a(n)  ___ ?

 a. Acid

 b. Base

 c. Conjugate acid

 d. Conjugate base

Answer: d

Acids donate or lose a hydrogen ion (proton). Bases accept or

gain a proton. Acids and bases by convention are located on the
left side of the reaction arrows. Conjugate acids are the bases
after they have accepted/added a proton. Conjugate bases are the
acids after they have donated/removed a proton. Conjugate acids
and bases by convention are located on the right side of the
reaction arrows. In this reaction, the butanoic acid has donated its
proton to pyridine to become the butonate anion. This anion can
now act as a base and is the conjugate base. For more examples
of this type of problem, see Skillbuilder 3.
Section 3.3

5. Using pKa table 3.1, page 100, what is the strongest base?

 a. H2O

 b. Br–

 c. NH3

 d. OH–

 e. CH3CH2–
Answer: e

Using the pKa table, refer to the conjugate base column. The
strength of base increases as you go down the column. The
CH3CH2– is the furthest down the column and therefore the
strongest base. For more examples of this type of problem, see
Skillbuilder 3.2.
Section: 3.3

6. Using pKa table 3.1, page 100, which base below is needed to
deprotonate the following structure?
H

 a. CH3CH2–

 b. F–

 c. NH2–

 d. OH–

 e. C6H5O–
Answer: a

Using the pKa table, refer to the conjugate base column. The
strength of base increases as you go down the column. The
conjugate base must be lower on the chart than the corresponding
acid. The CH3CH2– is the only base that is strong enough to
deprotonate the substrate. For more examples of this type of
problem, see Skillbuilder 3.3.
Section: 3.3

7. Using pKa values given, what is the product of the following reaction
(NH4+/NH3, pKa = 36)?

a.
c.

b.
d.
Answer: c

Only the carboxylic acid is acidic enough to be deprotonated by

the ammonia. For more examples of this type of problem, see
Skillbuilder 3.4.
Section: 3.4

8. Which of the following is the strongest base?

 a. H3C–

 b. H2N–

 c. HO–

 d. F–
Answer: a

The atoms containing the negative charge in the structures are in

the same period, so electronegativity is the deciding factor when
comparing basicity. More electronegative atoms are better able to
stabilize a negative charge, so d is the weakest base and a is the
strongest base.. For more examples of this type of problem, see
Skillbuilder 3.5.
Section: 3.4

9. Which of the following will have the conjugate acid with the
highest pKa?

 a. Br–

 b. Cl–

 c. F–

 d. I–
Answer: c

These bases are anions of atoms in the same group. Thus,

size is the dominant effect when comparing stability. Larger
atoms are better able to stabilize a negative charge, and thus I-
is the weakest base and F- is the strongest base. The stronger
the base the higher the pKa of the conjugate acid. For more
examples of this type of problem, see Skillbuilder 3.5.
Section: 3.4

10. Which of the following is the strongest acid?

 a. H2S

 b. HCl

 c. H3P

 d. SiH4
Answer: b

To compare acidity, consider the conjugate bases of these

compounds. S, Cl, P, and Si have a negative charge in the
conjugate base. Since these atoms are in the same period,
electronegativity is the dominant factor when comparing
stability. Cl is the most electronegative, thus Cl- is the most
stable conjugate base and HCl is the strongest acid. For more
examples of this type of problem, see Skillbuilder 3.5.
Section: 3.4

11. Which of the following is the most acidic?

A. B. C. H
H
H H
H
H
Answer: a

When structures have the most acidic proton on the same atom
(all of these have their most acidic proton on a carbon atom),
compare the orbitals of the lone pair in the conjugate bases.
Alkynes are sp hybridized. Alkenes are sp2 hybridized. Alkanes
are sp3 hybridized. The order of acidity is sp > sp2 > sp3
because the conjugate base is more stable when the lone pair
is in an sp orbital than sp2 and sp3. For more examples of this
type of problem, see Skillbuilder 3.8.
Section: 3.4

12. Which of the following is the most acidic?

A. B. C. D.
H H
O O O F3C O
F3C H H
O O
Answer: d

Inductive effect and resonance effect are the important factors

here. Structure C and D have both resonance structures and
strong inductive effect. Structure D has stronger inductive
effects because the fluorines are closer to the acidic hydrogen.
For more examples of this type of problem, see Skillbuilder 3.7.
Section: 3.4

13. The following structure is acetylsalicylic acid (Aspirin). Which

indicated proton is most acidic? (A-E)
Answer: A

Approaches to this problem include a) memorization of pKas

or look them up or b) compare the atom that the indicated proton
is attached for and check for size, electronegativity, orbitals,
resonance. In this case, B, C, D, and E are protons attached to
carbon. Only H is attached to the more electronegative oxygen.
Draw the potential conjugate bases to help students see what
equilibria are possible. For more examples of this type of
problem, see Skillbuilder 3.5.
Section: 3.5

14. Aspirin has a pKa of 3.5. In the stomach, of what form are the
majority of aspirin molecules?
Answer: A

The stomach has an approximate pH of 2. This is slightly

below the pKa of aspirin, which is equal to the pH that 50% of
aspirin molecules are in their neutral form and 50% are
deprotonated. Thus, most aspirin molecules will be in their neutral
form. For more examples of this type of problem, see
Skillbuilder 3.9.
Section: 3.5

15. Niacin (Vitamin B3) has a pKa of 4.85. In the blood, what is the
form of the majority of niacin molecules?
Answer: B

The blood has a pH of about 7.4. This is a few units above

the pKa of niacin, which is equal to the pH at which 50% of aspirin
molecules are in their neutral form and 50% are deprotonated.
Thus, most niacin molecules will be deprotonated. For more
examples of this type of problem, see Skillbuilder 3.10.
Section: 3.5

16. In which direction does the following equilibrium lie?

A. Left
B. Right
Answer: A

Compare the conjugate bases on each side. The conjugate

base on the left is more stable than the one on the right
because the Cl inductively withdraws electrons towards it,
which stabilizes it. Acid/base equilibria lie towards the more
stable conjugate base. For more examples of this type of
problem, see Skillbuilder 3.10.
Section 3.5

17. Which bases are strong enough to deprotonate H2O?

Answer: a, b, d, e

Water has a pKa of 15.7. The conjugate base of an acid with a

pKa higher than 15.7 can deprotonate water. For more
examples of this type of problem, see Skillbuilder 3.11.
Alternate Answers:

Section 3.5

17. Which bases are strong enough to deprotonate H2O?

 a. A, B, C, D, E

 b. B, C, D, E, F

 c. A, B, D, E

 d. B, C, D, E

 e. B, C, D, F
Answer: c

Water has a pKa of 15.7. The conjugate base of an acid with

a pKa higher than 15.7 can deprotonate water. For more
examples of this type of problem, see Skillbuilder 3.11.
Section 3.5

18. Which acids are strong enough to protonate an ethoxide ion

(CH3CH2O-)?

A. B. C. D. E. F.
H O
H HCl O H2SO4
H H OH
OH
Answer: c, d, e, f

The conjugate acid of the ethoxide ion has a pKa of 16.

Acids with pKa lower than 16 can protonate ethoxide. For
more examples of this type of problem, see Skillbuilder 3.11.
Alternate Answers:

Section 3.5

18. Which acids are strong enough to protonate an ethoxide ion

(CH3CH2O-)?

A. B. C. D. E. F.
H O
H HCl O H2SO4
H H OH
OH

 a. A, B, C, D

 b. B, C, D, E

 c. C, D, E, F

 d. A, C, D, F

 e. B, C, D, F
Answer: c

Ethoxide ion has a pKa of 16. Acids with pKa lower than 16
can protonate ethoxide. For more examples of this type of
problem, see Skillbuilder 3.11.
Section: 3.9

19. Which of the following structures are Lewis acids?

A. BF3 B. H2O C. NH3 D. AlCl3

 a. A

 b. B

 c. C

 d. D

 e. A
and D

 f. B
and C

 g. A, C
and D
Answer: e

Boron trifluoride and aluminum trichloride both have open p

orbitals that can accept electrons and act as Lewis Acids
(electron pair acceptors). For more examples of this type of
problem, see Skillbuilder 3.12.
Section: 3.9

19. Which of the following structures are Lewis acids?

A. BF3 B. H2O C. NH3 D. AlCl3

 a. A ONLY

 b. A and B

 c. A and C

 d. A and D

 e. All of them

Answer: d

Boron trifluoride and aluminum trichloride both have open p

orbitals that can accept electrons and act as Lewis Acids
(electron pair acceptors). For more examples of this type of
problem, see Skillbuilder 3.12.
Section: 3.9

20. Which of the following structures are Lewis bases?

A. B. C. D.
NH2 O

 a. A

 b. B

 c. C

 d. D

 e. A and D

 f. B and D

 g. B, C and D
Answer: g

Structures B, C and D all have lone pairs that can donate

electrons and act as Lewis Bases (electron pair donors). For
more examples of this type of problem, see Skillbuilder 3.12.
Section: 3.9

20. Which of the following structures are Lewis bases?

A. B. C. D.
NH2 O

 a. B ONLY

 b. B and C

 c. B and D

 d. B, C and D

 e. All of them

Answer: d

Structures B, C and D all have lone pairs that can donate

electrons and act as Lewis Bases (electron pair donors). For
more examples of this type of problem, see Skillbuilder 3.12.
Section: 3.1

21. Which of the following is the conjugate acid of CH3CH2NH2?

A. CH3CH2NH3+
B. CH3CH2NH2
C. CH3CH2NH−
D. −CH2CH2NH2
E. It depends on the acid or base it
reacts with.
Answer: A.

Conjugate acids have an additional proton compared to its

base.