Chapter 2 HW

1) A conjugate base of sulfuric acid is:

a) H3SO4+
b) SO3
c) HSO4
d) H2SO3
e) HSO3

2) Which of the following is not a Bronsted-Lowry acid?

a) H2O
b) (CH3)3N
c) NH4+
d) CH3CO2H
e) HCCH

3) Consider the equilibrium

PO 43- + H 2O HPO 42- + HO -
Which are the Bronsted-Lowry bases?
a) PO43 and HPO42
b) PO43 and OH
c) PO43 and H2O
d) H2O and OH
e) H2O and HPO42

4) What is/are the product(s) of the following acid-base mechanism?

O
H CH3O Na

CH3OH

Na
O
+ CH3OH
a)
O
+ CH3OH
b)
O OCH3
H

c)
Na O
+ CH3OH
d)
e) None of these choices.

5) What is/are the product(s) of the following acid-base mechanism?

 O
O
H Na H

O H
O
O
Na O
+ H2
O
a) O
O
O
+ H2
O
b) O

O Na
O H
+ H2
H
O
c) O

O Na
O
+ H2
O
d) O

e) None of these choices.

6) Which of the following is a Lewis acid?

a) H3O+
b) BF3
c) NF3
d) OH
e) More than one of these choices.

7) This species is a carbon-based Lewis acid:

a) CH4
b) HCCl3
c) CH3+
d) :CH3
e)·CH3

8) Which pair of species are both bases in the following reaction?

HCN + H2O -CN + H 3O +
a) H2O and CN
b) H3O+ and H2O
c) HCN and H3O+
d) HCN and CN-
e) H3O+ and CN

9) Which of the following organic compounds is the strongest acid?

a) C6H12 pKa = 52
b) CH3CH3 pKa = 50
c) CH3CH2OH pKa = 18
d) CH3CO2H pKa = 5
e) CF3CO2H pKa = 0

10) Which of the following substances has a hydrogen atom with pKa ≈25?
a) CH3CH2CH2CH2CO2H
b) CH3CHCH2C≡CCH3
c) CH3CH2CH2C≡CH
d) CH3CH2CH2CH2CH=CH2
e) CH3CH2CH2CH2NH2

11) Hydrogen atom(s) from which position(s) is (are) most likely to be abstracted when the
following substance is treated with NaH?
10 9
8
1
6 4 2
7 5 3

a) 1
b) 1, 5, 6
c) 1, 2
d) 3, 4, 7, 8, 9, 10
e) Hydrogens from all of the positions are equally likely to be abstracted by NaH.

12) Which is the strongest acid?

a) CH3CH2OH
b) CH3CO2H
c) HCCH
d) CH2=CH2
e) CH3CH3

13) Rank the bold-faced hydrogens for the following compounds from most acidic to least
acidic.
H
O
H
O O
H NH
CO2CH3
H N H

I II III IV V
a) I > IV > II > V > III
b) II > IV > I > V > III
c) II > IV > V > I > III
d) IV > I > II > V > III
e) IV > II > I > V > III

14) Rank the bold-faced hydrogens for the following compounds from most acidic to least
acidic.
H H
H
CH3 H
N
COO H H H
O
H
I II III IV V
a) I > II > III > IV > V
b) II > V > III > I > IV
c) II > III > V > I > IV
d) III > I > V > II > IV
e) V > II > III > I > IV

15) A group of acids arranged in order of decreasing acidity is:

HNO3 > CH3COOH > C6H5OH > H2O > HCCH

What is the arrangement of the conjugate bases of these compounds in decreasing order of
basicity?
a) NO3 > CH3COO > C6H5O > OH > HCC
b) CH3COO > C6H5O > NO3 > OH > HCC
c) C6H5O > NO3 > HCC > OH > CH3COO
d) HCC > OH > C6H5O > CH3COO > NO3
e) No prediction of relative base strength is possible.

16) Which of the acids below would have the strongest conjugate base?

a) CH3CH2OH pKa = 18
b) CH3CO2H pKa = 4.75
c) ClCH2CO2H pKa = 2.81
d) Cl2CHCO2H pKa = 1.29
e) Cl3CCO2H pKa = 0.66

17) Which of the acids below would have the strongest conjugate base?

a) CH3CH2OH pKa = 18
b) CH3CO2H pKa = 4.75
c) ClCH2CO2H pKa = 2.81
d) Cl2CHCO2H pKa = 1.29
e) Cl3CCO2H pKa = 0.66
18) Which is the strongest acid?
a) CH2ClCH2CH2CH2CH2CO2H
b) CH3CHBrCH2CH2CH2CO2H
c) CH3CH2CH2CBr2CH2CO2H
d) CH3CH2CH2CHFCH2CO2H
e) CH3CH2CH2CF2CH2CO2H

19) Which is the strongest acid?

a) CH2ClCH2CH2CH2CH2CO2H
b) CH3CHBrCH2CH2CH2CO2H
c) CH3CH2CH2CBr2CH2CO2H
d) CH3CH2CH2CHFCH2CO2H
e) CH3CH2CH2CF2CH2CO2H

20) What reactants would give the following products?

H
N
Reactants? Li +
O
Li
N
+

a) HO
O Li
N

b)
H
N
+

c) O
H

+ H N
O
d)
e) No reaction

21. Predict the outcome of the following acid-base reactions. Draw in the curved arrows that
demonstrate the movement of electrons in this reaction:
22. For each of the following reaction:
a. Label the acid and base
b. Label the conjugate acid and conjugate base.
c. Give the pKa for the acid and the conjugate acid.
d. Compare the pKas – which side of the reaction is favored? Why?