Chemistry 2440 - Quiz #2 - 10 points - Dr. Howard Black - Sept. 8, 2003 - KEY

1. (4 pts) Rate the following entities as Lewis acids (A), Lewis bases (B), or neither (N); do this by placing the appropriate letter (A, B, or N) on the line under the species.



2. (4 pts) The following questions will use the table below of several compounds and their pKa values


Compound pKa
Cl3CO2H 0.9
ClCH2CO2H 2.9
lactic acid 3.9
phenol 9.9
CH3CH2OH 15.9


a.
What compound is the most acidicCl3CO2(lowest pKa)

b. Draw the conjugate base of the least acidic molecule, showing resonance structures if appropriate:

CH3CH2O(no resonance possible)
(I wonder if that has anything to do with its low acidity....)

c. Rounding off the pKa values for phenol (to 10) and CH3CH2OH (to 16), which of these is the stronger acid? phenol  How many times more acidic is it than the weaker acid?

16 - 10 = 6   This is the difference in pKa units, which, like pH units, are reciprocal logs, so to get the actual difference, just raise 10 to the 6th power.  So, 106 = 1,000,000 = one million times more acidic

3. (2 pts) For the six molecules/ions below, decide whether each one is planar (P), nonpolar (N), or neither. Then, designate the planar/nonpolar entities by placing the letters P and/or N on the line below the species. In other words, the line below each molecule might have one letter, two letters, or none.