Organic Chemistry II KEY February 14, 2008
1. Which of the following starting material/ reagent combinations would give rise to
chlomiphene, a fertility agent? E
2. The major kinetic product(s) of the reaction of 2-methyl-2-pentene with Cl2, H2O is (are): A a) Organic Chemistry II KEY February 14, 2008
3. The major product of the reaction below is: B
4. Phase I metabolism of the anti-histamine, triprolidene involves an epoxidation process,
similar to the reaction of trans- 2-butene with p-chlorobperbenzoic acid. The epoxide metabolite(s) of triprolidine would be expected to be: B
a) a single stereoisomer b) a racemic mixture c) a mixture of only two diastereomers d) a mixture of multiple stereoisomers (enantiomers and
5. Which of the following alkenes would provide 1-bromo-1-methylcyclopentane as the major
kinetic product upon reaction with HBr without going through a rearrangement? C
a) I b) II c) I & II d) III & IV e) I, II, III, IV
Organic Chemistry II KEY February 14, 2008
6. Which of the following kinetically-controlled reactions will provide a racemic mixture as the
major products? A
7. Selegiline, an anti-histamine agent provides a ketone when reacted with aqueous acid and an
aldehyde when reacted with 1) BH3 and 2) H2O2, NaOH, H2O. Reaction with one equivalent of HCl gives a single product but reaction with one equivalent of Cl2 provides a mixture of stereoisomers. Which of the following structures represents selegiline? C Organic Chemistry II KEY February 14, 2008
8. Which of the following reaction intermediates is involved in the preparation of tramadol, an
analgesic, from treatment of the alkene (given below) with aqueous acid? A
9. Which set of reaction conditions will provide the product shown as the only product of the
reaction? A
10. Treatment of 1-methylcylobutene with 1) HgCl2, cyclobutanol and 2) NaBH4 will provide:
Organic Chemistry II KEY February 14, 2008
11. Which of the following alcohols will give methysticin the fastest upon treatment with
12. Which of the following alkenes will provide both of the products, A and B when reacted with
Organic Chemistry II KEY February 14, 2008
13. Which of the following reaction intermediates gives rise to the major kinetic product of the
reaction below? D
14. The carbonyl group of oxefedrine, an antianginal agent, is derived from which of the
following enols? D
15. Which of the following compounds can undergo E2 elimination? C Organic Chemistry II KEY February 14, 2008
16. Which of the following epoxides will give two ketone products when reacted with acid? (Assume no rearrangements occur) D
17. Reaction of compound I with sulfuric acid (no water) under thermodynamic conditions gives
compound II. Compound A (not a reaction intermediate) is generated from I and then goes on to react to give compound II. Which structure(s) represent(s) “A”? D
18. Rank the stability of the reaction intermediates below from most stable to least stable
(most>>least) B
a) II > I > > IV > III b) II > IV > I > III c) II > IV = I > III
d) I =IV > II > III e) I = II > IV > III
Organic Chemistry II KEY February 14, 2008
19. Which of the following reaction energy diagrams correspond to the reaction given below? D
20. Conversion of 2-methyl-2-butene to 2-methoxy-2-methylbutane can be accomplished with: D a) Organic Chemistry II KEY February 14, 2008
Questions 21-25: Matching column: Match the reactions (questions 21-25) with the appropriate set of reagents (choices a-e). Each reagent may be used once, more than once or not at all.
a) AcOH b) AcOH, H2O c) 1. m-ClPBA 2. AcOH d) 1. HgCl2, H2O 2. NaBH4
21. E 22. E 23. B 24. A 25. C
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