10. What is the major product from the following rearrangement?

6. Which sequence of reagents works best to convert 3-hexene to 3-hexyne? (A) 1. HCl 2. NaNH2 (B) 1. BH3．THF 2. HO- , H2O2 3. NaNH2 (C) 1. NaNH2 2. HI 3. H3O+ (D) 1. Br2, CH2Cl2 2. NaNH2 (excess) (E) 1. Cl2, CH2Cl2 2. NaCN(excess)

7. Which of the following technique(s) can readily distinguish between: (A) NMR (B) IR (C) MS (D) A and B (E) A and C

8. What is the major product of the following reaction?

9. What is the major product of the following reaction?

11. At what position of the pyridine ring in the coenzyme below will oxidation-reduction reaction take place?  (A) 1 (B) 2 (C) 3 (D) 4 (E) 5

12. Which of the following reaction is called Knoevenagel reaction? 

13. Which of the following structures is a Fischer projection of (2R,3R,4S)-2,3,4-tribromoheptane?(A)(B)(C)(D)(E) None of the above

14. Arrange the following substrates in order of their increasing SN2 reactivity with NaCN: (I) 1-bromopentane, (II) 1-chloro-2,2-dimethylpentane, (III) 2-bromo-2-methylpentane, and (IV) 1-chloro-3,3-dimethylpentane. (A) IV < II < I < III (B) III < I < IV < II (C) IV < II < III < I (D) III < II < IV < I (E) None of the above

15. Both [E]- and (Z)-hex-3-ene can be treated with D2 in the presence of a platinum catalyst. How are the products from these two reactions related to each other? (A) The [E]- and (Z)-isomers generate the same products but in differing amounts. (B) The [E]- and (Z)-isomers generate the same products in exactly the same amounts. (C) The products of the two isomers are related as constitutional isomers. (D) The products of the two isomers are related as diastereomers. (E) The products of the two isomers are related as enantiomers.

16. Consider the data illustrated below. The formula of unknown compound is C9H9N IR (cm-1): 3050, 2950, 2240, 1630 1H NMR (δ): 7.5 (2H, d), 7.1 (2H, d), 2.3 (2H, q), 0.9 (3H, t) 13C NMR (δ): 137 (s), 130, (s), 126 (d), 122 (d), 95 (s), 25 (t), 15 (q) The structure of unknown compound is? (A)(B)(C)(D)(E)