MULTIPLE CHOICE. Choose the one alternative that best completes the statement or answers the question. 1) Which of the following alkyl halides is a primary alkyl halide? A) I B) II C) III B) II and IV C) III and IV 2) A D) I and II 3) What is the IUPAC name of the following compound? A) 2-Chloro-4-methylpentane C) 2-Methyl-4-chloropentane C D) IV 2) Which of the following structures have the correct common name? A) II and III 1) B) 2-Chloro-1-isopropylpropane D) 2-Chloro-2-methylpentane 3) A 4) What is the IUPAC name of the following compound? A) (R)-6-Chloro-3-ethyloctane C) (S)-6-Chloro-3-ethyloctane 5) B B) I > II > III > IV D) II > IV > I > III 6) Rank the following molecules in order of increasing polarity, putting the least polar first. A) I < II < III < IV C) IV < III < II < I D B) (R)-3-Chloro-6-ethyloctane D) (S)-3-Chloro-6-ethyloctane 5) Rank the following halides in order of decreasing polarity, putting the most polar first. A) IV > II > I > III C) IV > III > II > I 4) 6) C B) II < I < III < IV D) I < IV < III < II 7) Which of the following statements about the reactions of alkyl halides is true? A) The characteristic reactions of alkyl halides are oxidation and reduction. B) The characteristic reactions of alkyl halides are elimination and substitution. C) The characteristic reactions of alkyl halides are addition and elimination. D) The characteristic reactions of alkyl halides are addition and substitution. 7) B 8) Rank the following in order of decreasing leaving group ability, putting the best first. A) III > II > IV > I C) II > III > I > IV D 9) D B) IV > I > II > III D) III > II > I > IV 9) Which of the following solvents is not a polar protic solvent? A) I 8) B) II C) III D) IV 10) Rank the following ions in order of increasing nucleophilicity in polar protic solvents, starting with the least nucleophilic ion. A) I < II < IV < III C) I < II < III < IV 10) B) IV < III < I < II D) IV < III < II < I 11) Which of the following anions is the most nucleophilic in polar aprotic solvents? A) IB) ClC) FD) Br- 11) 12) Which of the following is the most nucleophilic? A) HF B) NH3 C) H 2O 12) C D D) CH4 13) The reaction of bromoethane with sodium acetate affords the substitution product ethyl acetate. What is the effect of doubling the concentration of sodium acetate on the rate of the reaction? A) The rate remains the same. B) The rate decreases by a factor of 2. C) The rate increases by a factor of 2. D) The rate increases by a factor of 4. Sn2, therefore rate increases D 13) C C 14) Which of the following statements about SN 2 reactions is true? A) The mechanism is a two-step process. B) The fastest reaction will occur with a tertiary alkyl halide. C) Displacement occurs with inversion of configuration. D) The rate of reaction is dependent on just the substrate. 14) 15) Which of the following statements about the SN 2 mechanism for nucleophilic substitution reactions is true? A) Involves one step and occurs with inversion of configuration. B) Involves one step and occurs with retention of configuration. C) Involves two steps and occurs with inversion of configuration. D) Involves one step and occurs with racemization. 15) 16) Rank the alkyl halides in order of decreasing SN 2 reactivity, putting the most reactive first. 16) C 17) Which of the following statements about an SN 1 reaction mechanism is true? A) The reaction is fastest with primary alkyl halide. B) The reaction exhibits a one-step mechanism. C) The reaction rate increases as the strength of the nucleophile increases. D) The reaction rate increases as the leaving group ability increases. 17) C 18) Which of the following alkyl halides will react fastest with CH3OH in an SN 1 mechanism? 18) D 19) A primary A tertiary secondary A) III > I > II B) I > II > III C) II > I > III D) I > III > II tertiary A) I B) II C) III D) IV 19) Which of the following rate laws describes the kinetics of an SN 1 reaction? A) Rate = k[alkyl halide][nucleophile] B) Rate = k[alkyl halide] C) Rate = k[nucleophile] D) Rate = k[solvent]