71. Under what condition would phenylalanine exist as the following structure?

(A) at a low pH
(B) at a high pH
(C) at the pI
(D) when pH = pKa
(E) none of the above

72. Rank the bold hydrogens for the following compounds from most acidic to least acidic. I. (toluene with CF₃ and COOH, H on COOH) II. (alkene H) III. (oxonium H) IV. (benzene H) V. (phenol OH) (A) I ＞ II ＞ III ＞ IV ＞ V (B) III ＞ V ＞ II ＞ I ＞ IV (C) V ＞ II ＞ IV ＞ III ＞ I (D) III ＞ I ＞ V ＞ II ＞ IV (E) V ＞ III ＞ I ＞ II ＞ IV

73. Which will be the major product when trans-1-bromo-2-methylcyclohexane reacts with sodium isopropoxide in isopropanol? (A) I (cyclohexene) (B) II (methylcyclohexene) (C) III and IV (D) III (E) IV

74. Which conformation of trans-1-isopropyl-3-methylcyclohexane would be present in greatest amount at equilibrium? (A) The conformation with the methyl group equatorial and the isopropyl group axial. (B) The conformation with the methyl group axial and the isopropyl group equatorial. (C) The conformation with both groups axial. (D) The conformation with both groups equatorial. (E) The twist boat conformation.

75. Which of the following reagents can be used to convert cyclopentanol to cyclopentane? (A) TsCl, pyridine followed by LiAlH₄ (B) Na₂Cr₂O₇, H₂SO₄ (C) NaBH₄ followed by H₃O⁺ (D) H₂SO₄, heat followed by H₂, Pt-catalyst (E) both A and D

76. When two carbenes collide, they immediately dimerize to give? (A) an alkane (B) an alkene (C) an alkyne (D) an aromatic ring (E) a carbanion

77. Each of the diagram shown below represents the atomic orbitals that described the π electron system in butadiene: shade areas are positive; unshaded areas are negative. Which of these diagrams would be expected to represent the highest energy molecular orbital? (A) (B) (C) (D) (E) none of the above

78. Calculate the total number of unpaired electrons in the following complex ions: Zn(H₂O)₆²⁺, Ni(CN)₄²⁻ (square planar), Co(NH₃)₆³⁺ (strong field). (A) 0 (B) 1 (C) 2 (D) 3 (E) 4

79. Which will be the major product when diethyl heptanedioate reacts with sodium ethoxide? (A) I (B) II (C) III (D) IV (E) V

80. What is the symmetry of BF₃? (A) C₃ (B) C₃ᵥ (C) C₆ (D) D₃ₕ (E) D₆

81. How many moles of carbon dioxide are generated when one mole of the compound shown below (bicyclic alkene structure) is treated with warm, concentrated KMnO₄? (A) 1 (B) 2 (C) 3 (D) 4 (E) 8

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