Chem 240 - Spring 1999

First Exam, February 3, 1999

1. (8) Give correct IUPAC names for the following compounds.

a.
b.

2. (8) Draw structures which correspond to the following IUPAC names.

a. 4-methyl-2-pentanone b. 2,2-dimethylpropanal

 

 

 

3. (16) a. Circle the resonance relationship. Underline the tautomeric relationship

b. Circle the sp2 hybridized carbon atom. Underline the sp hybridized carbon atom(s).

c. Circle the Lewis base. Underline the Lewis acid.

d. Circle the functional group which is polar. Underline the functional group which has a pi (p) bond.

4 (24) Write structural formulas for the products of the following reactions.

a.

 

b.

 

c.

 

d.

 

e.

 

f.

5. (16) For each of the following reactions, place the structure of the needed reactant in the box.

 

a.

 

 

b.

 

 

c.

 

 

 

 

6. (12) The following compound might be made by a Grignard synthesis. Give structures for the necessary reactants and show the order of the steps you would take to carry out the synthesis.

 

 

 

 

 

 

 

 

7. (8) Write out the steps in the mechanism for the acid catalyzed reaction of benzaldehyde with butylamine. The overall reaction is shown below.

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

8. (8) A quote from the text: "Formaldehyde (H2C=O) exists in aqueous solution almost completely in the hydrate form (99+%), whereas only about 0.1% of acetone, (CH3)2C=O, is present as the hydrate." What structural influences explain this result? Illustrate your answer with reactions and structures.