8. Which of the following reagents will react with propane to give 2-propanol?
(A) H₂O/H₂SO₄
(B) MgOH
(C) NaBH₄
(D) Br₂/H₂O
(E) H₂O₂/Pt

9. Which of the following reagents can be used to prepare epoxide from alkenes? (A) MCPBA in methylene chloride (B) Peroxyformic acid in water (C) Formic acid in water (D) Peroxybenzoic acid in sodium hydroxide (E) Peracid in water

10. Which of the following best describes DDT? (A) A chlorocarbon used to decaffeinate coffee beans. (B) A polybrominated organic compound used as a herbicide. (C) A polychlorinated organic compound used as an insecticide. (D) Mixed alkyl halides used as an anesthetic. (E) Freon used as a foaming agent.

11. Sᴺ2 reactions usually proceed with: (A) Equal amounts of inversion and retention at the center undergoing substitution. (B) Slightly more inversion than retention at the center undergoing substitution. (C) Slightly more retention than inversion at the center undergoing substitution. (D) Complete inversion at the center undergoing substitution. (E) Complete retention at the center undergoing substitution.

12. Which of the following alkyl halides can produce only a single alkene product when treated with sodium methoxide? (A) 2-chloro-2-methylpentane. (B) 3-chloro-3-ethylpentane. (C) 3-chloro-2-methylpentane. (D) 2-chloro-4-methylpentane. (E) 2-chloro-3-ethylpentane.

13. What would be the reaction product(s) from the following E2 reaction? (A) (B) (C) (D) (E) No reaction

14. Which of the following compounds are chiral? (A) I only. (B) II and III. (C) III and IV. (D) I and IV. (E) V only.

15. Which of the following solvents could be described as polar aprotic? (I) ethanol, (II) acetonitrile, (III) dimethylformamide, (IV) THF, and (V) diethyl ether. (A) I only. (B) II and III. (C) III only (D) I and III. (E) III and V.

16. Which of the following alcohols is not likely to yield a product where skeletal rearrangement occurred when treated with sulfuric acid? (A) 3-methyl-3-pentanol. (B) 3,3-dimethyl-2-butanol. (C) 2,2-dimethylcyclohexanol. (D) cyclopentylmethyl alcohol. (E) 2,3-dimethyl-butan-2,3-diol.

17. If a mixture contains 75% of one compound and 25% of its enantiomer, what is the e.e. of the mixture? (A) 100. (B) 75. (C) 50. (D) 25. (E) 3.

18. Rank the following species in order of decreasing acid-dissociation constant: methanol (I), ethanol (II), 2-chloroethanol (III), t-butyl alcohol (IV), and phenol (V). (A) V ＞ IV ＞ III ＞ II ＞ I (B) V ＞ III ＞ I ＞ II ＞ IV (C) III ＞ V ＞ I ＞ IV ＞ II (D) V ＞ I ＞ III ＞ II ＞ IV (E) III ＞ IV ＞ V ＞ II ＞ I

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