Chemistry Department

 

University of Alberta

           

CHEM 263 B2

 

Exam II

 

Thursday, March 17, 2011

                                                                                                               

1.    The IR and ¹H NMR spectra of a compound of molecular formula C₉H₁₀O are given below. 

 

SDBSWeb : http://riodb01.ibase.aist.go.jp/sdbs/ (National Institute of Advanced Industrial Science and Technology, 1 March 2011)

 

 

 

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

 

(2 x 9 – 10 + 2)/2 = 5

 

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

 

Alcohol, aldehyde, ether, ketone, phenol

 

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

 

aldehyde

 

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

 

 

2.    Name the following compounds:

 

1. (3 points)

 

 

(E)-3-phenylpropenal

 

2. (4-points)

 

 

(R)-2-ethoxy-2-hydroxy-3-pentanone

 

3.    Draw the structures of the following molecules:

 

a.    3-nitrobenzenecarbaldehyde (3 points)

 

 

b.    1,3,5-trioxacyclohexane (3 points)

 

 

4.    What reagents would you use to effect the following conversions?  (21 points)

 

1.  

 

2.  

 

3.  

 

4.  

           

5.  

 

5.    Give the structure(s) of the principle organic products of the following reactions:  (15 points)

 

1.  

 

2.  

 

 

 

 

 

3.  

 

 

4.  

           

           

5.  

 

6.    Provide a synthetic pathway for the following transformations using the starting material provided and any other reagents:  (27 points)

 

1.  

 

 

 

 

2.  

 

 

 

3.  

 

 

 

7.    Propose a mechanism for the following reaction:  (8 points)

 

 

 

8.    Propose a mechanism for the following reaction:  (14 points)

 

 

Or accept initial attack by ethanol followed by ring closure.