Chemistry 2000 (Spring 2013)
Problem Set #8: Organic Reactions and Acid/Base Chemistry
Reading (Olmsted text)
 Chapter 10 Sections 10.5 – 10.7
 Chapter 14 (review; this was assigned reading in CHEM 1000)
 Chapter 15 Sections 15.1 – 15.2
Textbook Questions
 Chapter 10 Section Exercises
o 10.5.1 – 10.5.2
o 10.7.1 – 10.7.3
 Chapter 10 End-of-Chapter Problems
o 29abce, 33abde, 39, 41(should say “Problem 10.40(d)” not “Problem 10.40(e)”), 43, 45,
47, 49, 59, 61, 69, 73, 77
 Chapter 14 Section Exercises
o 14.1.1 – 14.1.4*
o 14.4.1 – 14.4.3
o 14.7.1 – 14.7.3
o 14.2.1 – 14.2.2*
o 14.5.1 – 14.5.3
o 14.3.1 – 14.3.3
o 14.6.1 – 14.6.3*
 Chapter 14 End-of-Chapter Problems
o 1*, 3*, 5*, 7*, 9*, 11*, 13*, 15*, 29*, 45*, 47*, 17, 27, 33, 35abc, 39, 41, 43, 49, 51, 57,
61, 63, 65, 71, 75ab, 77ab, 79, 81
 Chapter 15 Section Exercises
o 15.1.1 – 15.1.3
o 15.2.1 – 15.2.3
 Chapter 15 End-of-Chapter Problems
o 1, 3, 5, 7, 9, 11, 13, 15, 17, 19, 53, 57, 67, 69
Questions or question sets marked with a * cover review material.
Additional Practice Problems
1.
For each of the reactions below, draw the major organic product(s).
(a)
HBr
(b)
Cl2
(c)
H2O
H2SO4
(d)
H3C C C H
2.
(a)
(b)
(c)
3.
(a)
(b)
4.
excess HCl
There are six isomers (including both structural isomers and stereoisomers) with the molecular
formula C4H8.
Draw all six isomers of C4H8.
Identify which isomers will react with HCl. For those reactions which proceed, draw the product.
Identify which isomers will react with Br2. For those reactions which proceed, draw the product.
Which of the following bases can exist in aqueous solution?
CH3CO2OHSHNH2Which of the following acids can exist in aqueous solution?
CH3CO2H
NH4+
HF
HBr
CH3-
In order for a pharmaceutical to reach its target site, it is often necessary for it to be (at least
temporarily) water soluble. One strategy that can be used to improve the water solubility of a drug
is to convert an alcohol group to a sulfate ester:
O
R OH
R O S OH
O
This reaction is reversible, but the product is ideally stable enough to reach the target site.
The pKa of a typical sulfate ester is approximately -3 while the pKa of a typical alcohol is
approximately 15-19. Why does converting an alcohol group to a sulfate ester increase the water
solubility of a drug in a biological system (pH ~7)?
5.
When sodium hydroxide is added to hydrogen peroxide (H2O2), the following reaction occurs:
H2O2(aq)
(a)
(b)
(c)
(d)
+
OH-(aq)
H2O(l)
+
O2H-(aq)
Rewrite this equation using Lewis structures and show the movement of electrons using curly
arrows.
Which is a stronger acid, water or hydrogen peroxide? Suggest one reason why this might be so.
If the equilibrium constant for the reaction above is 200 at 25C, calculate the Ka and pKa of H2O2.
Hint: If you add two reactions (1 and 2), the overall equilibrium constant will be K1K2.
Calculate the Kb and pKb of O2H- (at 25C).