Organic Chemistry 354 Quiz - October 23, 1997
Dr. Sundin
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- 1. a. How many stereoisomers are in 2-deuterocitric acid,
HO2CCHDC(OH)(CO2H)CH2CO2H?
- b. Give a three dimensional sketch of (2R,3R)-2-deuterocitric acid.
- c. Dehydration of (2R,3R)-2-deuterocitric acid by the enzyme, Aconitase, gave Z-aconitic
acid, HO2CCH=C(CO2H)CH2CO2H.
Sketch Z-aconitic acid showing stereochemistry.
- d. Is this dehydration of (2R,3R)-2-deuterocitric acid an E1 or E2 reaction?
- e. Explain how one knows if it is E1 or E2. (Note that deuterium is gone.)
- f. In the laboratory, we dehydrate alcohols using concentrated sulfuric acid at
elevated temperatures. However, Aconitase catalyzes the dehydration at physiological pH
and physiological temperature. Aconitase contains an iron ion which gets involved in
the reaction. Are iron ions generally Lewis acids or Lewis bases?
- g. Suggest how the iron ion might catalyze this dehydration.
- 2. Give simple chemical tests to differentiate between members of the following pairs.
- a.
- b.
- 3. Starting from benzene and compounds containing no more than three carbon atoms, synthesize:
- a. p-nitrophenyl propyl ether
- b. cis-1,2-dihydroxycyclohexane
- b. trans-1,2-dihydroxycyclohexane
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