10. Which of the following amine can be resolved into enantiomers?
(A)
(B)
(C) 
(D)
(E)

11. At some temperatures, the relative reactivities of 3°, 2° and 1° alkane hydrogens in free radical chlorination are in the ratio of 5:3:1. What would be the expected percentages of monochlorination of isopentane produced? (i) 2-chloro-2-methylbutane, (ii) combined 1-chloro-2-methylbutane and 1-chloro-3-methylbutane, and (iii) 2-chloro-3-methylbutane. (A) 10% (i), 75% (ii), 15% (iii) (B) 25% (i), 45% (ii), 30% (iii) (C) 29% (i), 44% (ii), 18% (iii) (D) 30% (i), 35% (ii), 35% (iii) (E) 36% (i), 43% (ii), 21% (iii)

12. Rank the pKa values in the increasing order for the indicated protons. (A) Hb ＜ Hd ＜ He ＜ Hc ＜ Hₐ (B) Hₐ ＜ Hc ＜ Hd ＜ Hb ＜ He (C) He ＜ Hc ＜ Hd ＜ Hb ＜ Hₐ (D) He ＜ Hb ＜ Hd ＜ Hc ＜ Hₐ (E) Hb ＜ He ＜ Hd ＜ Hc ＜ Hₐ

13. Chih-Ming is an undergraduate student working in the organic chemistry laboratory. He found two compounds with chemical structure labelled on the round flasks from his senior's shelf in the fridge. Those compounds (I and II) are:  (A) constitutional isomers. (B) enantiomers. (C) identical. (D) diastereomers. (E) not isomeric.

14. Which of the final product is correct for the reactions listed below? (A) (B) (C) (D)  (E)

15. Which annulene would you not expect to be aromatic? (A) [6]Annulene (B) [14]Annulene (C) [16]Annulene (D) [18]Annulene (E) [22]Annulene

16. Which the following combination best answer the following questions (step-i to step-iii)? (i) what type of reaction is step-(i)? (ii) which is the correct condition for step-(ii)? (iii) which is the correct final product for step-(iii)?  (A) (Sₙ2) (CF₃C(O)OOH) (cyclopropane) (B) (E1) (H₂O₂, NaOH) (cyclopropane) (C) (E1cb) (CF₃C(O)OOH) (cyclopropane) (D) (E1cb) (CF₃C(O)OOH) (epoxide) (E) (E2) (H₂O₂, NaOH) (epoxide)

17. Remdesivir, one of the most popular molecules in the past three years, was approved or authorized for emergency use to treat COVID-19 in numerous countries. How many stereogenic centers are there in Remdesivir? (A) 4 (B) 5 (C) 6 (D) 7 (E) 8

18. (continued) Consider the ¹H-NMR spectrum of very pure Remdesivir. Presuming that      J  ab is sufficiently different from      J  bc and that the instrument has sufficient resolving power. Assuming the maximum multiplicity of signals and non-superposition of peaks, what is the expected signal splitting pattern for each signal, in the order (Hₐ, Hb, Hc). Note: s: singlet, d: doublet, t: triplet, dd: doublet of doublet, dt: doublet of triplet (A) d, dd, dt (B) s, dd, dt (C) d, dd, d (D) d, t, d (E) s, t, dt

19. In the following reactions, which is the correct major product? (A) (B) (C) (D) (E)

20. Starting with benzene, the best method for preparing para-nitrobenzoic acid is: (A) HNO₃/H₂SO₄; then CH₃Cl/AlCl₃; then separation of isomers; then KMnO₄/⁻OH/heat, followed by H₃O⁺. (B) CH₃Cl/AlCl₃; then HNO₃/H₂SO₄; then separation of isomers; then KMnO₄/⁻OH/heat, followed by H₃O⁺. (C) CH₃Cl/AlCl₃; then KMnO₄/⁻OH/heat, followed by H₃O⁺; then HNO₃/H₂SO₄. (D) HNO₃/H₂SO₄; then KMnO₄/⁻OH/heat, followed by H₃O⁺; then CH₃Cl/AlCl₃. (E) HNO₃/H₂SO₄; then CO₂, followed by H₃O⁺.

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