1. Using the following four data to estimate the ring strain in cyclobutane (ΔE₁) and cyclopentane (ΔE₂). If heat of combustion (in kJ/mol) of following four compounds are:

What is the number of AE1 + AE2 (in kJ/mol)?
(A) 400
(B) 450
(C) 500
(D) 550
(E) 600

2. Select the most acidic H in each of the following compounds (I and II), (A) Compound I: Hₐ, Compound II: Hₐ (B) Compound I: Hc, Compound II: Hc (C) Compound I: Hc, Compound II: Hₐ (D) Compound I: Hc, Compound II: He (E) Compound I: Hₐ, Compound II: He

3. Select the right configuration assignment (E or Z) for the following two alkenes. (A) Compound I: E, Compound II: E (B) Compound I: Z, Compound II: Z (C) Compound I: E, Compound II: Z (D) Compound I: Z, Compound II: E (E) None of above assignments is correct.

4. trans-1-tert-Butyl-4-isopropylcyclohexane has two conformers. Using the following data to calculate the strain in this two conformers, by how much kJ/mol that one is favored than the other?If, H-C-C-H eclipsed interaction strain: 4 kJ/mol;CH3-C-C-H eclipsed interaction strain: 6 kJ/molCH3-C-C-CH3 eclipsed interaction strain: 11 kJ/mol;CH3-C-C-CH3 gauche interaction strain: 3.8 kJ/mol     Each one      strain (S) of 1, 3-X-H diaxial interaction in monosubstitutedcyclohexane (kJ/mol):  (A) 9.2 (B) 22.8 (C) 32 (D) 16 (E) 11.4

5.  Select the right configuration assignment (R or S) for the following two compounds.  (A) None of below assignments is correct. (B) Compound I: S, Compound II: R (C) Compound I: R, Compound II: S (D) Compound I: R, Compound II: R (E) Compound I: S, Compound II: S

6. Select the right stability order for the following four Hexenes. Arrange the more stable alkene first.  ex: I (if it is your most stable one) > II > III > IV. (A) I ＞ II ＞ III ＞ IV (B) II ＞ III ＞ I ＞ IV (C) III ＞ II ＞ I ＞ IV (D) IV ＞ I ＞ II ＞ III (E) III ＞ II ＞ IV ＞ I

7. The optically pure tosylate of 2,2-dimethyl-1-phenyl-1-propanol ([α]D = -50°) was heated in acetic acid to yield the corresponding acetate ([α]D = +10°). If complete inversion had occurred, the optically pure acetate would have had [α]D = +50°. What percentage racemization occurred in this reaction? (A) 80% (B) 60% (C) 50% (D) 40% (E) 20%

8. For the following three compounds, select the      achiral      compound(s). (A) Compounds X and Y (B) Compounds X and Z (C) Compounds Y and Z (D) Only compound X (E) Only compound Z

9. Select the best fit chemical structure for compound X which with the following 1H NMR data.  (A) (B)(C) (D)(E)

10. If a H exhibits a triplet at δ 1.105, 1.085, and 1.065 ppm, data collected by a 300 MHz NMR. Where will this triplet peaks show up (δ:ppm) if this same sample was measured in a 600 MHz NMR? (A) 1.105, 1.085, 1.065 (B) 1.105, 1.095, 1.085 (C) 1.115, 1.085, 1.055 (D) 1.095, 1.085, 1.075 (E) 1.085, 1.075, 1.065

11. Select the best fit chemical structure for compound C₁₀H₁₀O₂ which with the following NMR data. ¹H NMR: δ 9.5 (1 H, d, J = 7 Hz), 7.5 (2 H, d, J = 6 Hz), 7.3 (2 H, d, J = 6 Hz), 6.8 (1 H, dd, J = 14, 7 Hz), 6.5 (1 H, d, J = 14 Hz), 3.6 (3 H, s). ¹³C NMR: δ 190, 145, 135, 130, 125, 120, 115, 60. (A) (B)(C) (D) (E)

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