Chemistry Department

 

University of Alberta

           

CHEM 261

 

Exam I

 

February 12, 2008

 

1. From the perspective of viewing along the bond between carbon 2 and carbon 3, draw the Newman projection of the most stable conformation of 2,3-dimethylbutane.

 

2. Give the structural formula of each of the following compounds:

 

a.    cis-4-isopropyl-2-octen-1-ol

 

b.    oxacyclobutane

 

3. Name the following compounds:

 

1.  

 

 

2.  

 

                       

                               

 

4. The pK_a of H₂ is 35 and that of (CH₃)₃COH is 18.

 

a.    Draw the products of the following reaction.

 

                       

 

b.    Determine the direction of the equilibrium and explain your answer.

 

5. In each of the following pairs of acids, circle the stronger base:

 

           

1.  

 

 

2.  

 

                       

 

 

3.  

 

           

6. The IR spectrum of a compound of molecular formula C₁₁H₈O is given below. Identify the functional group.

 

 

 

7. Calculate the degree of unsaturation indicated by the molecular formula C₁₁H₈O.

 

 

8. Juvenile hormone is produced by the male wild silk moth Hyalophora cecropia L., and its presence prevents the maturation of insect larvae:

 

           

           

a.      Name the oxygen-containing functional groups in Juvenile hormone.

 

b.      Estimate the bond angle labeled A.

 

c.      What is the classification of the carbon labeled B? (Primary, etc.)

 

d.      What is the hybridization of the oxygen labeled C?

 

9. Draw the functional group of a secondary amine.

 

10.  Draw the resonance structures of the following cation:

 

 

11. Compound A has molecular formula C₃H₆O.  Its IR spectrum shows no peaks in the 3500 - 3300 cm^-1 region and none in the 1650 - 1750 cm^-1 region.  Propose a structure for compound A.