Folder test bank is orgo chapter 8 ne wa

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In organic and inorganic chemistry, nucleophilic substitution is a fundamental class of reactions in which an electron nucleophile selectively bonds with or attacks the positive or partially positive charge of an atom or a group of atoms to replace a so-called leaving group; the positive or partially positive atom is referred to as an electrophile. The whole molecular entity of which the electrophile and the leaving group are part is usually called the substrate

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Folder test bank is orgo chapter 8 ne wa

  1. 1. Chapter 8
  2. 2. • 1. Identify the nucleophile in the following reaction. • • • • A. B. C. D. CH3Br OH¯ H2 O Br¯
  3. 3. • 2. Identify the leaving group in the following reaction. • • • • A. B. C. D. CH3CH2Br HS¯ Br¯ CH3OH
  4. 4. • 3. Which of the following cannot act as a nucleophile? • • • • A. B. C. D. NH3 H2O I¯ CH4
  5. 5. 4. • • • • In the SN2 reaction, the "2" stands for A. B. C. D. two reactants in the reaction. two steps in the reaction. two intermediates in the reaction. bimolecular kinetics for the reaction.
  6. 6. 5. Which of the following undergoes a substitution reaction with sodium cyanide in DMSO at the fastest rate? • • • • • A. B. C. D. CH3CH2F CH3CH2Cl CH3CH2Br CH3CH2I
  7. 7. 6. 1-Chloro-4-fluorobutane is reacted with one equivalent of sodium iodide in acetone. During the reaction a precipitate forms. What is the precipitate? • • • • A. B. C. D. FCH2CH2CH2CH2I ClCH2CH2CH2CH2I NaCl NaF
  8. 8. • 7. The rate law for the following reaction is • • • • A. B. C. D. rate = k[CH3CH2CH2Cl]. rate = k[CH3CH2CH2Cl][NaCN]. rate = k[CH3CH2CH2Cl][NaCN]2. rate = k[NaCN].
  9. 9. • 8. Which of the following reacts the fastest by the SN2 mechanism? • • • • • A. B. C. D. CH3Br CH3CH2Br (CH3)2CHBr (CH3)3CBr
  10. 10. • 9. Give the product(s) of the following reaction? • • • • A. B. C. D. A B C a mixture of A and B
  11. 11. • 10. Which halide ion reacts the fastest with cyclopentyl p-toluenesulfonate in ethanol/water? • • • • A. B. C. D. A B C D
  12. 12. • 11. Which one of the following species forms the strongest ion-dipole attraction with 18-crown-6? • • • • A. B. C. D. FK+ Cr2O72Br2
  13. 13. • 12. Identify the major product(s) in the reaction of (R)-2-bromopentane with sodium cyanide in DMSO? • • • • A. B. C. D. (R)-2-cyanopentane (S)-2-cyanopentane racemic mixture of 2-cyanopentane trans-2-pentene
  14. 14. • 13. Which of the following reacts fastest with methanol by the SN1 mechanism? • • • • A. B. C. D. A B C D
  15. 15. • 14. A pentacoordinate carbon is a transient species in the _____ mechanism. • • • • A. B. C. D. S N1 SN2 E1 E2
  16. 16. • 15. What is the leaving group in the following reaction? • • • • A. B. C. D. OHH2O CH3CH2+ C1-
  17. 17. • 16. Considering the SN1, SN2, E1, and E2 mechanisms, the energy diagram shown below corresponds to • • • • A. B. C. D. only the SN1 mechanism. only the SN2 mechanism. both the SN1 and E1 mechanisms. both the SN2 and E2 mechanisms.
  18. 18. • 17. Which of the following is the rate law for the SN1 mechanism of an alkyl halide with a nucleophile? • • • • A. B. C. D. rate = k[alkyl halide] rate = k[nucleophile] rate = k[alkyl halide][nucleophile] rate = k[alkyl halide]2[nucleophile]
  19. 19. • 18. Which of the following bases works best to maximize the E2 product in the reaction shown below? • • • • • A. B. C. D. KOCH2CH3 NaOCH2CH3 NaOC(CH3)3 NaOH
  20. 20. 19. Which of the following does not correctly describe SN2 reactions of alkyl halides? • A. Tertiary halides react faster than secondary halides. • B. Rate of reaction depends on the concentrations of both the alkyl halide and the nucleophile. • C. The mechanism consists of a single step with no intermediates. • D. The transition state species has a pentavalent carbon atom.

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