Chapter 7 Exam Questions PDF

Exam Name___________________________________ MULTIPLE CHOICE. Choose the one alternative that best completes the statement or answers the question. C 1) Which of the following alkyl halides is...

Exam Name___________________________________ MULTIPLE CHOICE. Choose the one alternative that best completes the statement or answers the question. C 1) Which of the following alkyl halides is a primary alkyl halide? 1) A) I B) II C) III D) IV A 2) Which of the following structures have the correct common name? 2) A) II and III B) II and IV C) III and IV D) I and II A 3) What is the IUPAC name of the following compound? 3) A) 2-Chloro-4-methylpentane B) 2-Chloro-1-isopropylpropane C) 2-Methyl-4-chloropentane D) 2-Chloro-2-methylpentane 1  D 4) What is the IUPAC name of the following compound? 4) A) (R)-6-Chloro-3-ethyloctane B) (R)-3-Chloro-6-ethyloctane C) (S)-6-Chloro-3-ethyloctane D) (S)-3-Chloro-6-ethyloctane B 5) Rank the following halides in order of decreasing polarity, putting the most polar first. 5) A) IV > II > I > III B) I > II > III > IV C) IV > III > II > I D) II > IV > I > III C 6) Rank the following molecules in order of increasing polarity, putting the least polar 6) first. A) I < II < III < IV B) II < I < III < IV C) IV < III < II < I D) I < IV < III < II B 7) Which of the following statements about the reactions of alkyl halides is true? 7) 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. 2  8) Rank the following in order of decreasing leaving group ability, putting the best first. 8) D A) III > II > IV > I B) IV > I > II > III C) II > III > I > IV D) III > II > I > IV 9) Which of the following solvents is not a polar protic solvent? 9) D A) I B) II C) III D) IV 10) Rank the following ions in order of increasing nucleophilicity in polar protic solvents, 10) D starting with the least nucleophilic ion. A) I < II < IV < III B) IV < III < I < II C) I < II < III < IV D) IV < III < II < I 11) Which of the following anions is the most nucleophilic in polar aprotic solvents? 11) C A) I- B) Cl- C) F- D) Br- 12) Which of the following is the most nucleophilic? 12) D A) HF B) NH3 C) H 2O D) CH4 C 13) The reaction of bromoethane with sodium acetate affords the substitution product ethyl 13) 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 3  C 14) Which of the following statements about SN 2 reactions is true? 14) 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. 15) Which of the following statements about the SN 2 mechanism for nucleophilic 15) A 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. 16) Rank the alkyl halides in order of decreasing SN 2 reactivity, putting the most reactive 16) C first. tertiary primary secondary A) III > I > II B) I > II > III C) II > I > III D) I > III > II 17) Which of the following statements about an SN 1 reaction mechanism is true? 17) C 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. D 18) Which of the following alkyl halides will react fastest with CH3OH in an SN 1 18) mechanism? tertiary A) I B) II C) III D) IV 19) Which of the following rate laws describes the kinetics of an SN 1 reaction? 19) A A) Rate = k[alkyl halide][nucleophile] B) Rate = k[alkyl halide] C) Rate = k[nucleophile] D) Rate = k[solvent] 4  20) Which of the following carbocations is the most stable? 20) B Most stable because it is tertiary A) I B) II C) III D) IV D 21) Which of the following is not a characteristic of an SN 1 reaction? 21) A) The reaction is favored in polar protic solvents. B) The electrophilic carbon undergoes only inversion of stereochemistry. C) The rate is proportional to the concentration of substrate. D) The rate is independent of the concentration of the nucleophile. 22) For the following reaction, use the identity of the alkyl halide and nucleophile to 22) B determine which substitution mechanism occurs. Then determine which solvent affords the faster reaction. nucleophile is always the same as solvent alkyl halide therefore can only be SN1 A) SN 2, DMSO B) SN 1, CH3OH C) SN 2, CH3OH D) SN 1, DMSO 23) For the following reaction, use the identity of the alkyl halide and nucleophile to 23) C determine which substitution mechanism occurs. Then determine which solvent affords the faster reaction. primary therefor SN2 A) SN 2, H2O B) SN 1, DMF C) SN 2, DMF D) SN 1, H2O 5  B 24) What is the product of the nucleophilic substitution reaction shown below? 24) A) Only I B) Only II C) I and II D) None 25) What is the product of the nucleophilic substitution reaction shown below? 25) C Tertiary therefore SN2 SN2 gives two products A) Only I B) Only II C) I and II D) None 26) What is the starting material in the reaction shown below? 26) D secondary secondary tertiary A) I B) II C) III D) IV 6 Answer Key Testname: UNTITLED2 1) A 2) A 3) A 4) D 5) C 6) D 7) B 8) D 9) B 10) C 11) C 12) B 13) C 14) C 15) A 16) C 17) D 18) D 19) B 20) B 21) B 22) B 23) C 24) B 25) C 26) D 7