Chem 335 - Winter 2002
Organic Chemistry II
Dr. Carl C. Wamser
1. (15 points) Write complete names for each of the following:
a) 
b) 
c) 
2 (15 points) Write clear structures or illustrations for each of the following:
a) 1-naphthalenecarboxylic acid
b) 2-methoxypyridine
c) trans-3-vinylcyclopentanol
d) allyl methyl sulfide
e) any benzylic Grignard reagent
3. (15 points) Complete each reaction by adding the missing part: either the starting materials, the necessary reagents and conditions, or the final major product.
a) 
b) 
c) 
d) 
e) 
4. (15 points) Complete each reaction by adding the missing part: either the starting materials, the necessary reagents and conditions, or the final major product.
a) 
b) 
c) 
d) 
e) 
5. (20 points) Write a complete mechanism for the Friedel-Crafts acylation of bromobenzene with acetyl chloride using aluminum chloride catalyst.
Show all steps and all resonance forms for any intermediates involved for the pathway to the expected major product.
6. (30 points) Write THREE synthetic sequences that can be used to prepare 1-bromo-1-phenylpropane. All must start with benzene and 1-propanol.
a) using a Grignard reagent
b) using a Gilman (organocopper) reagent
c) using a Friedel-Crafts acylation
7. (15 points) Write a balanced equation for the following reaction:
8. (15 points) Write a complete mechanism for the reaction
shown below.
Show all steps and all resonance forms for any intermediates involved.
The indicated product is the major product, but one other product is formed in significant yield as well.
Draw the structure of the other product and illustrate how it would be formed.
9. (15 points) Write a complete mechanism for the reaction
shown below.
Show all steps and all resonance forms for any intermediates involved.
10. (15 points) Write all resonance forms for the cationic intermediates that would be formed in the following reactions:
a) 
b) 
c) 
11. (15 points) Compound A ( C7H6O ) reacts with compound B ( C3H3Na ) to form (after aqueous workup) compound C ( C10H10O ).
Both A and C can be oxidized with hot acidic dichromate to benzoic acid.
B shows only a sharp singlet in proton NMR.
C shows prominent bands in its IR spectrum at 3400 and 2150 cm-1.
Identify compounds A, B, and C.
12. (15 points) Identify the unknown compound of molecular formula C10H14O that gives the following data:
IR:
no absorptions in the 3200 - 3600 cm-1 range
no absorptions in the 1700 - 1800 cm-1 range
1-H NMR:
1.0 ppm / doublet / 3H
2.5 ppm / multiplet / 1H
3.5 ppm / singlet / 3H
3.8 ppm / doublet / 2H
7-8 ppm / multiplet / 5H
13-C NMR:
2 peaks in the 10-40 range
2 peaks in the 50-65 range
4 peaks in the 110-170 range
