Dr. Andrew L. Korich
Grand Valley State University
Bronsted-Lowery Acid-Base Chemistry
Last Updated: September 13, 2016
1. Draw the Lewis dot structure of each of the following acids and rank them in INCREASE order (least
to most) of acidity.
A. Methane
B. Ethanol
C. Acetic Acid
D. Hydrochloric Acid
E. Acetylene
F. Ethylene
Ranking: (Least) _____< _____< _____< _____< _____< _____ (Most)
2. For acetylene, ethylene and methane explain the relationship between hybridization and acidity. Be
sure to clearly articulate and justify your rational.
3. For each chemical reaction a) label the acid, base, conjugate acid and conjugate base; b) identify the
pka value of the acid and conjugate acid; c) indicate if the equilibrium is located toward the reactions
or products.
+
HCl
O
H2O
+
+
Cl
H2O
K OH
OH
+
H3O
O
O K
H
Na OH
+
+
H2O
1
Dr. Andrew L. Korich
Grand Valley State University
Bronsted-Lowery Acid-Base Chemistry
Last Updated: September 13, 2016
O
H3C
H
N
N
+
O
+
CH3
H3C
O
NH3
OH
+
OH
HBr
O
+
NH4
CH2
O
OH2
+
Br
4. Predict the products of each acid-base reaction. Indicate if the equilibrium favors the reactants or the
products.
+
NH2
H
H
H2SO4
+
+
K2CO3
Na NH2
OH
O
+
5. Rake the following organic molecules in increasing order of acidity. Place a box around the
molecules that can be deprotonated using KOH.
H
OH
OH
O
OH
A
B
C
D
Ranking: (Least) _____< _____< _____< _____ (Most)
2
Dr. Andrew L. Korich
Grand Valley State University
Bronsted-Lowery Acid-Base Chemistry
Last Updated: September 13, 2016
6. Rank the following molecules in INCREASING (weakest to strongest) order of basicity.
NH
O
A
B
C
NH2
D
Ranking: (Least) _____< _____< _____< _____ (Most)
O
Br
A
B
O
O
C
D
Ranking: (Least) _____< _____< _____< _____ (Most)
7. Using proper arrow formulism, draw a reaction mechanism for each acid-base reaction
O
+
O H
O
H3C
OH
+
H
O
H O S OH
O
+
CH3
NH3
H Br
+
3