Chemistry Department

 

University of Alberta

           

CHEM 263 B1

 

Exam I

 

Thursday, February 11, 2010

 

1.    The IR and ¹H NMR spectra of a compound of molecular formula C₁₀H₁₂O are given below. 

 

 

SDBSWeb : http://riodb01.ibase.aist.go.jp/sdbs/ (07-01-10)

 

 

a.    Calculate the degree of unsaturation. (1 point)

 

b.    List the possible functional groups gleaned from the molecular formula. (2 points)

 

c.    What is the functional group that the IR spectrum shows to be present in the unknown? (2 point)

 

d.    Propose a structure for this compound. (10 points)

 

2.    Propose a structure for the compound that fits the following data: (5 points)

 

C₃H₄Br₂                d = 4.19 ppm (2H, singlet)

                                    d = 5.63 ppm (1H, singlet)

                              d = 6.03 ppm (1H, singlet)

 

3.    Sketch the expected ¹H NMR spectrum of the following compound:

 

 

           

 

4.    Consider the following reaction which involves one equivalent of HCl:

 

 

a.    Draw the product(s) of this reaction.

 

b.    Propose a mechanism that accounts for the formation of the product(s).

 

c.    Draw the thermodynamic product.

 

5.    Propose a mechanism that accounts for the following reaction:

 

 

6.    Provide a synthetic pathway for the following transformation: