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  1. Which dimethylcyclobutane is chiral?

    A) 1,1-dimethylcyclobutane
    B) trans-1,2-dimethylcyclobutane
    C) cis-1,3-dimethylcyclobutane
    D) cis-1,2-dimethylcyclobutane
    B) trans-1,2-dimethylcyclobutane
    (this multiple choice question has been scrambled)
  2. What is the relationship between an enantiomer's configuration and its specific rotation?

    A) There is no relation
    B) R are dextrorotatory
    C) R are levorotatory
    A) There is no relation
    (this multiple choice question has been scrambled)
  3. (+)-Mandelic acid has a specific rotation of +158 degrees. What specific rotation would be observed for a sample with 50% optical purity?

    A) 79.0 degrees
    B) 00.0 degrees
    C) 39.5 degrees
    D) 52.7 degrees
    B) 00.0 degrees
    (this multiple choice question has been scrambled)
  4. Which best defines a meso compound?

    A) a molecule that has no mirror image
    B) a molecule that cannot be superposed on its mirror image even though it has no chiral centers
    C) a molecule with a plane of symmetry and no chiral center
    D) a molecule that can be superposed on its mirror image and that does contain chiral centers
    D) a molecule that can be superposed on its mirror image and that does contain chiral centers
    (this multiple choice question has been scrambled)
  5. Which of the following compounds is a meso compound?

    A) trans-1,2-dichlorocyclopropane
    B) cis-1,2-dichlorocyclopropane
    C) 1,1-dichlorocyclopropane
    D) cis-1-chloro-2-bromocyclopropane
    B) cis-1,2-dichlorocyclopropane
    (this multiple choice question has been scrambled)
  6. If a molecule has 5 stereogenic center, it will have __?__ stereoisomers

    A) 32
    B) 25
    C) 5
    D) 0
    A) 32
    (this multiple choice question has been scrambled)
  7. This process occurs when both bonding electrons remain with one product fragment.

    A) Heterolytic bond breaking
    B) radical formation
    C) homolytic bond formation
    D) homolytic bond breaking
    A) Heterolytic bond breaking
    (this multiple choice question has been scrambled)
  8. How many degree of unsaturation are in valium (diazepam),?

    A) 10
    B) 11
    C) 7
    D) 12
    B) 11
    (this multiple choice question has been scrambled)
  9. In a radical reaction, the following step, is an example of___?___.
    Cl⋅+CH3-CH2-CH3 → CH3-CH-CH3 + HCl

    A) initiation
    B) propagation
    C) addition
    D) termination
    B) propagation
    (this multiple choice question has been scrambled)
  10. The reason that the chemical shift for an alkyne hydrogen atom is upfield from an alkene hydrogen atom is:

    A) it is more acidic than the alkene hydrogen atoms.
    B) the alkyne carbon has a grate relative electronegativity due to the fact that it is sp hybridized.
    C) there are 2 pi bonds for resonance in the alkyne versus only 1 pi bond in the alkene.
    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.
    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.
    (this multiple choice question has been scrambled)
  11. Which of the following will be the most abundant fragment ion formed from 2-butanone in the mass spectrum? 

    A) CH3
    B) CH3-CH3+
    C) CH3-C☰O:+
    D) CH3-CH2-C☰O:+
    D) CH3-CH2-C☰O:+
    (this multiple choice question has been scrambled)
  12. Why is the infrared absorption for the stretching motion of internal alkynes rarely observed?

    A) They are too strong.
    B) C☰C stretching does not change the dipole moment.
    C) They do not form cations.
    D) The force constant for stretching of C☰C is too high.
    B) C☰C stretching does not change the dipole moment.
    (this multiple choice question has been scrambled)
  13. Why is the oxygen-hydrogen absorption of CH3OH such a broad band in the infrared?

    A) Hyperconjugation resonance broadens the absorption.
    B) Hydrogen bonding broadens the absorption.
    C) Resonance broadens the absorption.
    D) Rotational energy levels broaden the absorption.
    B) Hydrogen bonding broadens the absorption.
    (this multiple choice question has been scrambled)
  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

    A) Greater/inductive and/or Anisotropic effects.
    B) Greater/resonance effects.
    C) Less/resonance effects.
    D) Less/inductive and/or anisotropic effects.
    A) Greater/inductive and/or Anisotropic effects.
    (this multiple choice question has been scrambled)
  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

    A) Triplet
    B) Doublet
    C) Singlet
    D) Quartet
    D) Quartet
    (this multiple choice question has been scrambled)
  16. What is the intensity ratio of the peaks of a quartet in a  spectra?

    A) 1:4:4:1
    B) 1:1:1:1
    C) 1:2:2:1
    D) 1:3:3:1
    D) 1:3:3:1
    (this multiple choice question has been scrambled)
  17. Which of the following molecule orbital diagrams for butadiene represents the highest occupied molecular orbital in the excited state?

    A) ⇞-⇞↗⇟-⇟
    B) ⇞-⇟↗⇟-⇞
    C) ⇞-⇟↗⇞-⇟
    D) ⇞-⇞↗⇞-⇞
    A) ⇞-⇞↗⇟-⇟
    (this multiple choice question has been scrambled)
  18. The amount of energy in infrared light corresponds to:

    A) The amount of energy needed to "flip" the spin of a 13C or a 1H nucleus.
    B) The amount of energy needed to increase certain molecules motions, such as bond vibrations.
    C) The amount of energy needed to strip a molecules of one electron to generate a cation radical.
    D) The amount of energy needed to promote one electron from a bonding to an antibonding molecular orbital.
    B) The amount of energy needed to increase certain molecules motions, such as bond vibrations.
    (this multiple choice question has been scrambled)
  19. The major monobromination product in the following reaction is:


    A)
    B) 
    C) 
    D) 
    C)
    (this multiple choice question has been scrambled)
  20. Which compounds give four signals in their ^1H spectra?
    I. (CH3)2CHCH2CH3
    II. H3CHC=CH2
    III.CH3(Br)CHCH2CH3

    A) All of these
    B) II and III
    C) III only
    D) I only
    E) II only
    F) I and II
    G) None of these
    H) I and III
    A) All of these
    (this multiple choice question has been scrambled)
  21. How many absorptions will the following compound have in its CMR spectrum?
    CH3CH2CH=C(CH3)2

    A) 2
    B) 5
    C) 4
    D) none of these
    E) 3
    D) none of these
    (this multiple choice question has been scrambled)
  22. Which characterizes the splitting of the indicated protons in the structure below?
    (Cl)CH=CHCH2Cl H's in trans

    A) singlet
    B) doublet of doublet
    C) triplet
    D) doublet
    E) none of these
    D) doublet
    (this multiple choice question has been scrambled)
  23. How many peaks are present in the NMR signal for the starred protons.
    CH3-CH2-CH2-CH2-CH3

    A) 4
    B) 5
    C) 2
    D) 3
    E) none of these
    B) 5
    (this multiple choice question has been scrambled)
  24. Which of the following alkene is expected to have the highest heat of hydrogenation?

    A) 2-methyl-2-butene
    B) trans-2-pentene
    C) cis-2-pentene
    D)1-pentene
    D)1-pentene
    (this multiple choice question has been scrambled)
  25. Which of the following is not a possible reaction of a carbocation?

    A) Addition of a nucleophile
    B) Rearrangement to a more stable carbocation
    C) Addition of a proton to form an alkane
    D) Loss of a Beta-hydrogen to form an alkene
    C) Addition of a proton to form an alkane
    (this multiple choice question has been scrambled)
  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.
    B) C=C pi bonds are attacked by nucleophiles.
    C) C=C double bonds are weak.
    D) C=C double bonds are unstable.
    A) A pi bond is lost but a stronger sigma bond is gained.
    (this multiple choice question has been scrambled)
  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?

    A) 3-chloro-3-methylpentane
    B) 3-chloro-2-methylpentane
    C) 1-chloro-3-methylpentane
    D) 2-chloro-2-methylpentane
    A) 3-chloro-3-methylpentane
    (this multiple choice question has been scrambled)
  28. Predict which of the following alkenes react the fastest with HCl.

    A) CH3CH2CH2CH2CH=CH2
    B) cis-CH3CH2CH=CHCH2CH3
    C) trans-CH3CH2CH=CHCH2CH3
    D) (CH3)2C=CHCHH2CH3
    D) (CH3)2C=CHCHH2CH3
    (this multiple choice question has been scrambled)
  29. Which of the following alkenes gives 1-bromo-2-methyl-2-pentanol upon reaction with Br2/H2O?

    A) CH3CH2C-(CH3)HCH=CH2
    B) CH3CH2CH=C(CH3)2
    C) CH3CH2CH2C-(CH3)=CH2
    D) CH3CH=CHCH(CH3)2
    C) CH3CH2CH2C-(CH3)=CH2
    (this multiple choice question has been scrambled)
  30. Which of the following is least likely to react with an alkene?

    A) CH3CH2 (ethyl radical)
    B) NaOCH2CH3
    C) BrCl
    D) H3O+
    B) NaOCH2CH3
    (this multiple choice question has been scrambled)
  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.
    B) Methyl shift from C-3 to C-2.
    C) Hydride shift from C-2 to C-1.
    D) Proton shift from C-2 to C-1.
    A) Hydride shift from C-3 to C-2.
    (this multiple choice question has been scrambled)

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