Chemistry Department

 

University of Alberta

           

CHEM X61

 

Exam I

 

October 19, 2006

 

1. The IR spectrum of a compound of molecular formula C₆H₁₅N is given below. Identify the functional group.

 

 

 

 

 

 

 

 

 

 

 

2. Calculate the degree of unsaturation indicated by the molecular formula C₈H₁₀ClNO.

 

      Calculate the degree of unsaturation indicated by the molecular formula C₈H₁₂ClNO.

 

      Calculate the degree of unsaturation indicated by the molecular formula C₈H₁₄ClNO.

 

 

      Calculate the degree of unsaturation indicated by the molecular formula C₈H₁₆ClNO.

 

3. Name the following compounds:

 

1.  

 

 

 

 

 

 

 

 

 

2.  

 

                       

 

                       

                       

 

                       

                       

 

                       

                       

 

                       

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

 

1. 1,3-dioxacyclopentane

 

                1,3-dioxacyclohexane

 

                1,3-dioxacycloheptane

 

                1,3-dioxacyclooctane

                       

2. 2,3-dimethylbicyclo[4.3.0]nonane

 

2,4-dimethylbicyclo[4.3.0]nonane

 

2,3-dimethylbicyclo[4.2.0]octane

 

2,4-dimethylbicyclo[4.2.0]octane    

 

5. Viracept is an antiviral drug used to treat HIV:

 

           

           

a.         Name the oxygen-containing functional groups in Viracept.

 

b.         Estimate the bond angle labeled A.

 

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

 

d.         What is the classification of the carbon labeled C? 

 

6. Draw the resonance structures of the azide ion N₃^-, a linear ion.

 

7.  Draw the functional group of an ester.

 

8. Compound A has molecular formula C₃H₉N and is soluble in 1M HCl.  Its IR spectrum shows no peaks in the region 3500 - 3300 cm^-1.  Propose a structure for compound A.

 

9. CH₃COCH₂COCH₃ has a pK_a of 9.0 and the pK_a of H₂O is 15.7.

 

a)        Will CH₃COCH₂COCH₃ react with NaOH?                                 

 

b)        Explain your answer.

 

10. The pK_a of H₂ is 35 and that of HCΞCH is 25.

 

a.      Draw the products of the following reaction.

 

                       

 

b.      Determine the direction of the equilibrium.                       

 

11. In each of the following pairs of acids, circle the stronger acid:

           

1.  

 

 

2.  

 

                                    

 

3.  

 

                 

 

12. The pK_a of CH₃NO₂ is 10, making its C-H bond more acidic than most C-H bonds.  Explain using Lewis structures.