Organic Chemistry 354 Quiz - September 30, 1999
Dr. Sundin
- 1. Give the structure of the products of 1,2-dimethylcyclohexene
with the following. Give the stereochemistry if it is known.
If no reaction occurs, write NR.
- a. HBr
Answer
- b. Dilute KMnO4, NaOH, room temperature
Answer
- c. H2, Pd
Answer
- d. Br2, CCl4
Answer
- 2. Which reactions in 1 above are:
- a. Stereoselective with syn addition
Answer
- b. Stereoselective with anti addition
Answer
- 3. Give the structure of the alkene you would hydrate (alkene plus
water and acid) to give the following alcohol.
Answer
- 4. Compound A, C8H16, had a carbon-13 nmr
spectrum which revealed six different carbon atoms. A reacted with
dilute, basic permanganate solution to give a brown-black precipitate.
When A was treated with hot, acidic permanganate, two compounds,
B, C3H6O, and
C, C5H10O2, were formed.
The carbon-13 nmr spectrum of B revealed two different carbon atoms.
The carbon-13 nmr spectrum of C revealed three different carbon atoms.
- a. _______ How many rings are in A?
Answer
- b. _______How many pi bonds are in A?
Answer
- c. Is B a ketone or a carboxylic acid?
Answer
- d. Is C a ketone or a carboxylic acid?
Answer
- e. What are the structures of A, B, and C?
Answer
- 5. Give the structure of the product and the mechanism for the
reaction of 1,2-dimethylcyclopentene and bromine.
Answer
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