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CHEMISTRY 2311-EXAMINATION IV
DECEMBER 11, 1998
DR. MARK A. FORMAN
NAME:
QUESTION POINTS SCORE
1 7 _______
2 9 _______
3 8 _______
4 6 _______
5 6 _______
6 9 _______
7 10 _______
8 6 _______
9 9 _______
10 18 _______
11 12 _______
TOTAL _______
- Provide an IUPAC name for each of the following compounds (7 points). a.) (^) b.) c.) CH 3 ________________ _________________
Br Br
- Draw structures corresponding to each of the following IUPAC names (9 points). a.) p -chlorobenzoicacid b.) 2,4,6-trinitrophenol c.) 2-chloro-1,4-dintrobenzene
- a.) Circle all compounds that are expected to be aromatic. You may assume that all are planar (8 points). O
- The five-membered heterocycle imidazole is aromatic. Draw an orbital picture of imidazole to accountfor its aromaticity. Be sure to include a discussion of the hybridization of the nitrogen atoms in your answer (6 points). H^ N^ N
- Briefly explain why the –CFinductive and/or resonance effects of the –CF 3 group is a meta-directing deactivator. Be sure to include a discussion of 3 group in your answer (6 points).
- Define each of the following terms in words, with a chemical structure, or with an equation (9 points). a.) a charged aromatic compound b.) a Friedel-Crafts acylation reaction c.) a deactivating; o,p-director
- Predict the product of each of the following reactions (18points). a.) (^) SO 3 H
OH
HNO 3 , H 2 SO 4 b.) CH 2 CH (^3) Br 2 , FeBr 3
c.) O C CH 2 CH (^3) CH 3 CH 2 Cl, AlCl 3
d.) OH , AlCl 3 CH 3 CH^3
Cl COCH 3
- Show how you would accomplish each of the following syntheses, listing all required reagents andshowing all transformations (12 points). a.) (^) NO 2 Br
b.) (^) CH 2 CH 2 CH 3 Cl
