37. Which sequence of steps below describes the best synthesis of 5-oxohexanoic acid starting with 1-methylcyclopentan-1-ol?
(A) 1. Conc. KMnO₄; 2. Dry gaseous HBr; 3. Mg/ether; 4. CO₂
(B) 1. H₂SO₄ and heat; 2. Conc. KMnO₄
(C) 1. Conc. KMnO₄; 2. CH₃MgBr/ ether; 3. H₃O⁺
(D) 1. H₂SO₄ and heat; 2. O₃; 3. (CH₃) ₂S; 4. PCC
(E) 1. H₂SO₄ and heat; 2. Conc. KMnO₄; 3. LiAlH₄; ₄. H₃O⁺

33. Which of the following compounds will react with methyl vinyl ketone in a Robinson annulation to generate the cyclic enone below?  (A) 1-pentene (B) cyclohexanone (C) 2-pentanone (D) pentanal (E) None of the above

34. Provide the structure of the major organic product in the reaction below. (A)(B)(C)(D)(E)

35. The product of the following reaction immediately undergoes a dimerization at room temperature. What is the structure of the dimer? (A) (B) (C) (D) (E)

36. For the following multistep synthesis, choose the best reaction conditions to give the desired product? (A) (i) HBr, (ii) O3 followed by Zn/H+ , (iii) Li/NH3 (B) (i) NaNH2/NH3 followed by CH3CH2I, (ii) Lindlar’s catalyst/H2, (iii) OsO4 followed by NaHSO3 (C) (i) H2/Pd/C (1 equivalent), (ii) NaNH2/NH3 followed by CH3CH2Br, (iii) KMnO4/H2O (D) (i) HgSO4/H2O/H2SO4, (ii) Lindlar’s catalyst/H2, (iii) OsO4 followed by NaHSO3 (E) (i) Lindlar’s catalyst/ H2, (ii) NaNH2/NH3 followed by CH3CH2Br, (iii) OsO4 followed by NaHSO3

38. Which of the following amines could be formed by reduction of an amide? (I) benzylamine (II) isopropylamine (III) aniline (IV) triethylamine (A) I (B) III & IV (C) I & IV (D) II & III (E) I, III & IV

39. What is the major product of the following reaction? (A) I (B) II (C) III (D) IV (E) V

40. Predict the major product of the following reaction sequence. (A) I (B) II (C) III (D) IV (E) V

41. Predict the major product of the following dehydration reaction. (A) I (B) II (C) III (D) IV (E) V

42. Which of the following oxidants will convert a primary alcohol to an aldehyde? (I) sodium dichromate /sulfuric acid (II) copper oxide (III) pyridinium chlorochromate (IV) dimethylsulfoxide, oxalyl chloride (A) III & IV (B) II, III & IV (C) III (D) I, II, III & IV (E) None of the above

43. Protons Ha and Hb in the following compound are? CH3 Ha Hb CH3 (A) homotopic (B) enantiotopic (C) diastereotopic (D) mesotopic (E) None of the above