Chemistry 201-101
Test # 3
November 10, 2011
Dr. Richard Rogers
Name: _______________________________________
1. Give the major elimination and/or substitution product(s) for the following reactions. Hints:
consider the relative nucleophilicity vs. basicity vs. steric bulk for each nucleophile/base.
Amide anions are much better bases than nucleophiles while organic sulfides are much
better nucleophiles than bases. (12 points)
2. Calculate the number of degrees of unsaturation of a compound with a molecular formula
of C8H6Cl2N2O. (5 Points)
3. Draw the structure of 5-bromo-6-methyl-2-phenylhepta-2E,4Z-diene. (5 points)
4. Draw the product of the following elimination reactions. Hint: think anti-coplanar. (15
points)
5. Draw the structure of the three products generated by the following dehydration reaction
and circle the major product. (6 points)
6. Predict the product of the following reactions. (18 points)
7. Give the reagents (A-E) necessary to carry out the reaction sequence shown below. (15
points)
8. On the following pages are several infrared spectra. For each spectra list the functional
group(s) that is (are) present. There may be more than one functional group present!
Some examples of functional groups are: alcohol, amine, alkene, nitrile alkyne, aldehyde,
conjugated aldehyde, ketone, conjugated ketone, carboxylic acid, conjugated carboxylic
acid, amide, conjugated amide, ester, conjugated ester. (24 points)