19. What method will produce the transformation? 

 
(A) Li / ND₃
(B) (sia)₂BD then H₂O
(C) CH₃CH₂MgBr then D₃O⁺
(D) (sia)₂BD then D₂O
(E) LiAlD₄ then D₂O

15. When indole is treated with bromine in dioxane at 0o C, the major organic product is . (A) 2-bromoindole (B) 3-bromoindole (C) 4-bromoindole (D) 5-bromoindole (E) 6-bromoindole

16. Which compound has a 1 H NMR spectrum consisting of the following peaks: 0.9 (6H, d), 1.0 (3H, t), 2.2 (2H, q), and 4.0 (1H, septet)? 

17. How many distinct alkene products are possible when the alkyl iodide below undergoes E2 elimination?  (A) 1 (B) 2 (C) 3 (D) 4 (E) 5

18. Which of the following describes the compound below?  (A) bridged bicyclic (B) fused bicyclic (C) spiro bicyclic (D) bridged tricyclic (E) fused tricyclic

20. Energy is __________ when bonds are formed and is __________ when bonds are broken; therefore, bond dissociation energies are always __________. (A) released / consumed / exothermic (B) released / consumed / endothermic (C) consumed / released / exothermic (D) consumed / released / endothermic (E) consumed / released / isothermic

21. Which of the following are correct Lewis structures, including formal charges, for nitric acid, HNO3?  (A) A only (B) B only (C) C only (D) both B and C (E) A, B, and C

22. Which of the following alkyl chlorides is least likely to undergo rearrangement during a solvolysis reaction? (A) cis-1-chloro-2-ethylcyclohexane (B) trans-1-chloro-2-ethylcyclohexane (C) 2-chloro-4-methylpentane (D) 2-chloro-3-methylpentane (E) 2-chloro-2-methylpentane

23. Which of the following descriptions of the nucleoside uridine does not apply to the structure of the molecule? (A) The uracil base is directly bonded to the 1' position of ribofuranose in the α position. (B) The ribofuranose moiety is found in only the D configuration. (C) Nitrogen, at position 1 in the uracil base, is directly bonded to the ribofuranose moiety. (D) The 5' OH group is replaced with phosphate(s) in the nucleotide structure. (E) none of the above

24. Which of the following is correct in order of decreasing nucleophilicity toward methyl iodide in methanol? (A) CH3O- > CH3S- > CN- > Br- (B) CH3O- > CN- > CH3S- > Br- (C) CN- > CH3O- > CH3S- > Br- (D) CH3S- > Br- > CH3O- > CN- (E) CH3S- > CN- > CH3O- > Br-

25. Which of the following compounds will undergo SN2 reaction most readily? (A) (CH3)3CCH2I (B) (CH3)3CCl (C) (CH3)2CHI (D) (CH3)2CHCH2CH2CH2I (E) (CH3)2CHCH2CH2CH2Cl