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Organic Test

23 Questions
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Questions and Answers
  • 1. 
    Provide two  circumstances under which solvolysis of chiral alkyl halide would not result in the generation of a mixture of enantiomeric products. 
  • 2. 
    Which of the following statements correctly describe(s) E1 reactions of alkyl halides (RX)?I.    Rate= k[base]II.   Rate= k[base][RX]III.  Rate= k[RX]IV. The reactions occur in twwo or more distinct steps.V.  Rearrangements are sometimes seen.     A) III and V           B) II and IV           C) I,IV, and V          D) I only      E) III,IV, and V
  • 3. 
    Which of the compounds below undergoes solvolysis in aqueous ethanol most rapidly?
    • A. 

      3-chloropentane

    • B. 

      3-iodo-3-methylpentane

    • C. 

      Methyl iodide

    • D. 

      Cyclohexyl bromide

  • 4. 
    When ioniztion occurs at the single sterocenter of a chiral compound, the resulting carbocation is:
    • A. 

      Achiral

    • B. 

      Racemic

    • C. 

      Optically active

    • D. 

      Chiral

    • E. 

      None of the above

  • 5. 
    Which alkanes have largely replaced Freons as propellants in aerosol cans?
    • A. 

      Pentane and hexane

    • B. 

      Methane and ethane

    • C. 

      Propane and butane

    • D. 

      Nonane and decane

    • E. 

      None of the above

  • 6. 
    Which of the following statements is(are) true for the compound (3R, 4R)-3,4-dimethylhexane?
    • A. 

      This compound is chiral.

    • B. 

      This compound is a diastereomer of (3R, 4S)-3,4-dimethylhexane.

    • C. 

      The enantiomer of this compound is (3S, 4S)-3,4-dimethylhexane.

    • D. 

      All the above

    • E. 

      None of the above

  • 7. 
    Which of the following correctly expressed the standard Gibbs free energy change of a reaction in terms of the changes in enthalpy and entropy?
    • A. 

      DG°= DH° + TDS°

    • B. 

      DG°= DS° + TDH°

    • C. 

      DG°= DS° - TDH°

    • D. 

      DG°= DH° - TDS°

  • 8. 
    Which of the following reactive intermediates can best be descibed as both nucleophilic and strongly basic?
    • A. 

      Free radicals

    • B. 

      Carbanions

    • C. 

      Alkanes

    • D. 

      Carbocations

    • E. 

      Carbenes

  • 9. 
    Which of the following statements is(are) true for the compound (R)-butanol?
    • A. 

      This compound is optically active.

    • B. 

      This compound has enantiomer.

    • C. 

      This compound is chiral.

    • D. 

      All the above

    • E. 

      None of the above

  • 10. 
    In the first propagation step of the free radical chlorination of methane, which of the following occurs?
    • A. 

      A chlorine radical abstracts a hydrogen

    • B. 

      A carbon radical reacts with Cl2

    • C. 

      Cl2 dissociates

    • D. 

      A carbon radical reacts with a chlorine radical

    • E. 

      Two chlorine radicals combine

  • 11. 
    The major product from the reaction of 2-chloro-2-methylpentane with sodium ethoxide in ethanol results from which of the following mechanistic pathways?
    • A. 

      SN2

    • B. 

      SN1

    • C. 

      E1

    • D. 

      E2

    • E. 

      E1cb

  • 12. 
    What term describes the structural relationship between (E)- and (Z)-2-pentene?
    • A. 

      Conformers

    • B. 

      Not isomers

    • C. 

      Constitutional isomers

    • D. 

      Enantiomers

    • E. 

      Diastereomers

  • 13. 
    The bond dissociation energy is the amount of energy required to break a bond_____.
    • A. 

      Homolytically

    • B. 

      So as to produce the more stable pair of ions

    • C. 

      Heterolytically

    • D. 

      Via hydrogenation

    • E. 

      None of the above

  • 14. 
    Which of the following is a vicinal dihalide?
    • A. 

      Isobutyl chloride

    • B. 

      Trans-1,4-diiodocyclohexane

    • C. 

      3,3-dichloropentane

    • D. 

      Cis-1,2-dibromocyclopentane

    • E. 

      1,3-dibromoheptane

  • 15. 
    Which of the following best describes DDT?
    • A. 

      A polybrominated organic compound used as a herbicide

    • B. 

      A polychlorinated organic compound used as an insecticide

    • C. 

      A mixed alkyl halide used as an anesthetic

    • D. 

      A chlorocarbon used to decaffinate coffee beans

    • E. 

      A Freon used as a foaming agent

  • 16. 
    Which of the following is true for the initiation step of a free radical chloroniation reaction?
    • A. 

      DH° = 0 and DS°<=0

    • B. 

      DH° > 0 and DS°> 0

    • C. 

      DH° > 0 and DS°< 0

    • D. 

      DH° < 0 and DS°> 0

    • E. 

      DH° < 0 and DS°< 0

  • 17. 
    Given the chloronation of acetone sown below, choose the correct rate law.   CH3COCH3 + Cl2 ® CH3COCH2Cl + HCl
    • A. 

      Rate = [CH3COCH3]

    • B. 

      Rate = [CH3COCH3][Cl2]

    • C. 

      Rate = [CH3COCH3][Cl2]1/2

    • D. 

      Rate = [Cl2]

    • E. 

      Cannot be determined from stoichometry; must be determined experimentally

  • 18. 
    What term describes the structural relationship between cis-1,2-dimethylcyclopentane and trans- 1,3-dimethylcyclopentane?
    • A. 

      Enantiomers

    • B. 

      Constitutional isomers

    • C. 

      Conformers

    • D. 

      Diastereomers

    • E. 

      Not isomers

  • 19. 
    Which of the following is a carbene?
    • A. 

      NCO-

    • B. 

      CH2=CHO-

    • C. 

      CH3CH2·

    • D. 

      CH3CH2+

    • E. 

      :CCl2

  • 20. 
    Which of the following statements correctly pertains to a pair of enantiomers?
    • A. 

      They rotate the plane of polarized light by differing amounts and in opposite directions.

    • B. 

      They rotate the plane of polarized light by differing amounts and in the same direction.

    • C. 

      They have different melting points.

    • D. 

      They have the same melting point, but they have different boiling points,

    • E. 

      They rotate the plane of polarized light by exactly the same amount and in opposite directions.

  • 21. 
    How many carbons do the primary alkane constituents of gasoline contain?
    • A. 

      C1-C2

    • B. 

      C8-C12

    • C. 

      C3-C4

    • D. 

      C12-C16

    • E. 

      C5-C8

  • 22. 
    Which of the following correctly lists the conformations of cyclohexane in order of increasing energy?
    • A. 

      Chair

    • B. 

      Chair

    • C. 

      Half-char

    • D. 

      Half-chair

    • E. 

      Chair

  • 23. 
    ______ is the study of reaction rates.
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