48. For the reaction shown, which of the compounds listed below would be the expected major, and final, organic product?  
(A) I
(B) II
(C) III
(D) IV
(E) V

44. What is the major product of the following reaction? 1. OsO4, pyridine ?   

45. The 1 H NMR spectrum of which of the compounds below, all of formula C7H12O2, would consist of three singlets only? (A) I (B) II (C) III (D) IV (E) V

46. Arrange the following in order of increasing basicity: aniline, p-nitroaniline, p-toluidine, and p-methoxyaniline. (A) p-toluidine < p-methoxyaniline < aniline < p-nitroaniline (B) p-nitroaniline < p-toluidine < aniline < p-methoxyaniline (C) p-nitroaniline < aniline < p-toluidine < p-methoxyaniline (D) p-methoxyaniline < p-nitroaniline < p-toluidine < aniline (E) None of the above 

47. What is the thermodynamic product of the sulfonation of naphthalene?

49. Predict the major product for the following Claisen rearrangement. (A) I (B) II (C) III (D) IV (E) None of the above

50. Predict the major product for the following reaction.  (A) I (B) II (C) III (D) IV (E) V

51. Which of the following reagents can be used to cleave a tert-butoxycarbonyl (Boc) protecting group from a peptide? (A) H2/Pd (B) CF3CO2H (C) Na2CO3, H2O (D) LiAlH4 (E) None of the above

52. The reaction shown below would be expected to produce as major products which of the following compounds?(A)+ enantiomer(B)  + enantiomer (C)  + enantiomer (D)  + enantiomer (E)  + enantiomer

53. What is the best method for the preparation of m-dibromobenzene from benzene? (A) 1). HNO3/H2SO4; 2). Sn/HCl; 3). NaNO2/HCl, 0°C; 4). Br2/FeBr3, twice. (B) 1). HNO3/H2SO4; 2). Sn/HCl; 3). NaNO2/HCl, 0°C; 4). Br2/FeBr3; 5). H3PO2. (C) 1). HNO3/H2SO4; 2). Sn/HCl; 3). NaNO2/HCl, 0°C; 4). H3PO2; 5). Br2/FeBr3, twice. (D) 1). HNO3/H2SO4; 2). Br2/FeBr3; 3). Sn/HCl; 4). NaNO2/HCl, 0°C; 5). CuBr. (E) Br2/FeBr3, twice.

54. Which is the best method for the synthesis of tert-butyl methyl ether? (A) CH3ONa + (CH3)3CBr → (B) (CH3)3CONa + CH3I → (C) CH3OH + (CH3)3COH + H2SO4 at 140°C → (D) (CH3)3CONa + CH3OCH3 →(E) CH3ONa + (CH3)3COH →