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  1. Which dimethylcyclobutane is chiral?




    B) trans-1,2-dimethylcyclobutane
  2. What is the relationship between an enantiomer's configuration and its specific rotation?



    A) There is no relation
  3. (+)-Mandelic acid has a specific rotation of +158 degrees. What specific rotation would be observed for a sample with 50% optical purity?




    B) 00.0 degrees
  4. Which best defines a meso compound?




    D) a molecule that can be superposed on its mirror image and that does contain chiral centers
  5. Which of the following compounds is a meso compound?




    D) cis-1,2-dichlorocyclopropane
  6. If a molecule has 5 stereogenic center, it will have __?__ stereoisomers




    C) 32
  7. This process occurs when both bonding electrons remain with one product fragment.




    A) Heterolytic bond breaking
  8. How many degree of unsaturation are in valium (diazepam),?




    C) 11
  9. In a radical reaction, the following step, is an example of___?___.
    Cl⋅+CH3-CH2-CH3 → CH3-CH-CH3 + HCl




    D) propagation
  10. The reason that the chemical shift for an alkyne hydrogen atom is upfield from an alkene hydrogen atom is:




    D) the anisotropic effect of the triple bond shields the alkyne hydrogen atoms whereas the anisotropic effect of the double bond deshields the alkene hydrogen atom.
  11. Which of the following will be the most abundant fragment ion formed from 2-butanone in the mass spectrum? 




    B) CH3-CH2-C☰O:+
  12. Why is the infrared absorption for the stretching motion of internal alkynes rarely observed?




    A) C☰C stretching does not change the dipole moment.
  13. Why is the oxygen-hydrogen absorption of CH3OH such a broad band in the infrared?




    B) Hydrogen bonding broadens the absorption.
  14. The beta alkene carbon atom (marked with a star) of the following compund will have a chemical shift in the carbon NMR spectrum _?_ than the normal shift for ethene () primarily due to _?_.
    H2C★=CH-F




    B) Greater/inductive and/or Anisotropic effects.
  15. What is the multiplicity expected in the ^1 spectrum for the hydrogen atoms marked by a "star" in the following compound?
    CH3-C(=O)- ★CH2-CH3




    D) Quartet
  16. What is the intensity ratio of the peaks of a quartet in a  spectra?




    B) 1:3:3:1
  17. Which of the following molecule orbital diagrams for butadiene represents the highest occupied molecular orbital in the excited state?




    B) ⇞-⇞↗⇟-⇟
  18. The amount of energy in infrared light corresponds to:




    D)  The amount of energy needed to increase certain molecules motions, such as bond vibrations.
  19. The major monobromination product in the following reaction is:





    C)
  20. Which compounds give four signals in their ^1H spectra?
    I. (CH3)2CHCH2CH3
    II. H3CHC=CH2
    III.CH3(Br)CHCH2CH3








    H) All of these
  21. How many absorptions will the following compound have in its CMR spectrum?
    CH3CH2CH=C(CH3)2





    B) none of these
  22. Which characterizes the splitting of the indicated protons in the structure below?
    (Cl)CH=CHCH2Cl H's in trans





    D) doublet
  23. How many peaks are present in the NMR signal for the starred protons.
    CH3-CH2-CH2-CH2-CH3





    D) 5
  24. Which of the following alkene is expected to have the highest heat of hydrogenation?




    D) 1-pentene
  25. Which of the following is not a possible reaction of a carbocation?




    B) Addition of a proton to form an alkane
  26. Which statement most accurately describes why alkenes react the way they do?




    A) A pi bond is lost but a stronger sigma bond is gained.
  27. Addition of HCl to 3-methyl-1-pentene gives two products. one of these is 2-chloro-3-methylpentane. What is the other product?




    B) 3-chloro-3-methylpentane
  28. Predict which of the following alkenes react the fastest with HCl.




    C) (CH3)2C=CHCHH2CH3
  29. Which of the following alkenes gives 1-bromo-2-methyl-2-pentanol upon reaction with Br2/H2O?




    C) CH3CH2CH2C-(CH3)=CH2
  30. Which of the following is least likely to react with an alkene?




    D) NaOCH2CH3
  31. The rearrangement which occurs in the following reaction can be described as a

    (CH3)2CHCH=CH2 -HBr->
                3   2    1



    A)  Hydride shift from C-3 to C-2.
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