67. What is the rearrangement product of 3,3-dimethyl-1-butene reacting with HCl?
(A) 3-chloro-2,2-dimethylbutane
(B) 1,2-dichloro-3,3-dimethylbutane
(C) 1-chloro-3,3-dimethylbutane
(D) 2-chloro-3,3-dimethylbutane
(E) 2-chloro-2,3-dimethylbutane

68. Which of the following exhibits the correct (increasing) orders for atomic radius and ionization energy, respectively? (A) Atomic radius: F, S, O; ionization energy: O, S, F (B) Atomic radius: F, O, S; ionization energy: S, O, F (C) Atomic radius: S, O, F; ionization energy: F, O, S (D) Atomic radius: S, F, O; ionization energy: S, F, O (E) None of the above

69. To determine the calcium carbonate (CaCO3) content in a 500.0 mg solid sample, a chemist prepared two identical flasks (sample flask and blank flask), each containing exactly the same volume and concentration of hydrochloric acid (HCl). For sample flask, 500.0 mg sample was added, allowing the CaCO3 to react completely with the HCl. For the blank flask, no sample was added; this flask represents the total initial amount of HCl. After the reaction completed, the acid in both flasks was titrated with 0.1000 M NaOH. The blank flask required 45.00 mL of NaOH, while the sample flask required 25.00 mL of NaOH. What is the mass of CaCO3 in the sample? (Molar mass of CaCO3 = 100.0 g/mol) (A) 50.0 mg (B) 100.0 mg (C) 200.0 mg (D) 250.0 mg (E) 450.0 mg

70. In an E2 reaction, what geometric relationship must exist between the leaving group and the β-hydrogen? (A) Syn-periplanar (B) Gauche (C) Anti-periplanar (D) Forming a 90° dihedral angle (E) Can be randomly oriented

71. A quartet and a triplet (area ratio 2:3) in 1H-NMR most likely indicates the presence of a(n) ______. (A) Ethyl group (B) Isopropyl group (C) tert-Butyl group (D) Propyl group (E) Vinyl group

72. A chemist uses the standard addition method to determine the concentration of copper (Cu2+) in a river water sample to account for matrix interferences. Two 25.0 mL aliquots of the river water are processed as follows: Solution A: 25.0 mL of the sample is diluted to a final volume of 50.0 mL with distilled water. The measured absorbance is 0.25. Solution B: 25.0 mL of the sample plus 1.00 mL of a 500 ppm Cu2+ standard is diluted to a final volume of 50.0 mL. The measured absorbance is 0.50. Assuming the absorbance is directly proportional to the Cu2+ concentration, what is the concentration of Cu2+ in the original river water sample? (A) 5.0 ppm (B) 10.0 ppm (C) 20.0 ppm (D) 25.0 ppm (E) 40.0 ppm

73. At a certain temperature, the half-life of a zero-order reaction is 40.0 minutes. How long will it take for the reactant concentration to be reduced by 75%? (A) 40.0 min (B) 60.0 min (C) 80.0 min (D) 120.0 min (E) 160.0 min

74. Which of the following molecules can undergo the Cannizzaro reaction? (A) Acetaldehyde (B) Benzaldehyde (C) Acetone (D) Cyclohexanone (E) Propionaldehyde

75. An analyst uses a HPLC method to determine a pesticide residue. A 1.00 ppm standard solution of the pesticide produces a peak height (signal) of 40.0 mV. When a blank solution is injected, the standard deviation of the baseline noise is measured to be 0.20 mV. Using the common IUPAC criterion of S/N = 3, what is the Limit of Detection (LOD) for this method (assuming the signal is directly proportional to the analyte concentration)? (A) 0.005 ppm (B) 0.015 ppm (C) 0.045 ppm (D) 0.060 ppm (E) 0.150 ppm

76. A compound with the sum formula C3H6O has an IR peak at 1715 cm-1 and only one singlet in 1H-NMR. The compound is ______. (A) Propionaldehyde (B) Acetone (C) Allyl alcohol (D) Propylene oxide (E) Methyl vinyl ether

77. In mass spectrometry, a molecule with one bromine atom shows M and M+2 peaks in a ratio of approximately ______. (A) 1:1 (B) 3:1 (C) 1:3 (D) 9:6:1 (E) 1:2:1

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