Practice Problems

Monday, October 24, 2005 1. Quinine is a compound that was used extensively for the treatment of malaria. a. Identify the hybridization of the atoms indicated by arrows. b. Identify the two most basic sites in this molecule. Which is more basic? Why?

N OH

quinine

2. Rank the following in order of decreasing boiling point:

O NH2

OH OH

3. Draw all the isomers of C5H10 (there are 9 excluding stereoisomers, 11 including stereoisomers). Name them all. PS this is good practice, but much too long to expect on an actual exam. 4. Rank the following in order of increasing basicity:

OH N

5. Rank the following in order of increasing pKa: HCl, HOCl, HOOH, HONH2, H2O

6. Rank the following compounds in order of polarity. Rank them in order of boiling point.
Cl Cl Cl

7. Using the pKa table in your book, calculate the equilibrium constant for each of the following reactions. On which side of the equation does the equilibrium lie? Explain the difference in pKa between acetic acid and ethanol.
O H N OH OO H2+ N

H N OH O-

H2+ N

8. The compound named 1,4-dimethylbicyclo[2.2.2]octane is sometimes called paddlane. Draw it as a line drawing. 9. Decalin can exist as two different isomers cis and trans. Draw clear 3-D representations of cis and trans-decalin. Which is more stable? Why?

decalin

10. Draw 2-methyl-3-chloro-1-pentanol as a line drawing.

11. Name the following compounds according to IUPAC rules:

H3C CH3

OH

Cl

12. There are two possible stereoisomers for the last compound in the previous problem. Give a clear 3-D representation of the most stable conformer of both stereoisomers. Which is more stable? 13. There are 2 isomers of 1-tert-butyl-3-methylcyclohexane. Identify them, and for each one, draw the preferred conformation in clear 3-D drawings. 14. Identify all the isomers of 1,2-dichlorocyclohexane. Draw all possible chair conformations of these isomers. Rank them in order of polarity. Rank them in order of stability. 15. You would like to make 2-bromobutane from an alcohol. What starting material and reagents should you use? 16. Predict the products of the following reactions. If you expect multiple products, indicate which one will be the major product. If you expect no reaction, say so.

Cl2

PBr3
OH

I2