Assessment Exam:Organic

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  1. What structure has a parent name heptane?(2)
    A. CH3(CH2)2CH(CH3)CH2C(CH3)2
    B. (CH3)3C(CH2)3CH(CH3)CH2CH3
    C. CH3(CH2)2C(CH3)2CH=CHCH2CH3
    D. (CH3)2CHCH(CH3)CH(CH3)2

  2. What orbitals overlap to form the indicated C-C bond?(5)
    Org5:
    A. sp3-sp2
    B. sp2-sp2
    C. sp2-sp
    D. sp-sp3

  3. The large difference in the boiling point of these two compounds can be explained by which factor?(9)
    org9:
    A. the steric effect of the methyl group in compound 1
    B. a resonance effect in compound 1
    C. hydrogen bonding between molecules of compound 2.
    D. the electron donation of the methyl group in compound 2


  4. Which reaction coordinate diagram is most likely to represent the reaction pathway? (12)

    CH3CH2 CH2 CH2Cl + CN- --> CH3CH2 CH2 CH2CN + Cl-
    A. org4a:
    B. org4b:
    C. org4c:
    D. org4d:

  5. What R and/or S configuration notation would be used for this structure?(21)
    A. 2R,3R
    B. 2S,3R
    C. 2R,3S
    D. 2S,3S

  6. What is the major product from this reaction, if it takes place via a SN2 pathway?(23)
    A.
    B.
    C.
    D.

  7. What is the product of this Diels-Alder reaction?(35)
    A.
    B.
    C.
    D.

  8. What is the order of reactivity of these substituted benzenes toward electrophilic aromatic substitution?(39)
    A. I>II>III
    B. II>I>III
    C. III>II>I
    D. III>I>II

  9. When allowed to react with HCl, which alkene will give an alkyl chloride in which the carbon skeleton has changed?(40)
    A. CH3CH2C(CH3)=CHCH3
    B. CH2=CHC(CH3)2
    C. CH3CH=CHCH2CH(CH3)2
    D. CH3C(CH3)2)CH=CH2

  10. What is the mmajot product of this reaction?(45)
    A.
    B.
    C.
    D.

  11. What would be the product of careful hydrogenation of 3-hexyne with one equivalent of hydrogen and Lindlar (poisoned Pd) catalyst?(54)
    A. CH3CH2 CH2 CH2 CH2 CH3
    B. org54b:
    C. org54c:
    D. CH3CH2COOH

  12. Which polymer would be produced by this reaction?(60)
    A.
    B.
    C.
    D.

  13. Which site(s) in the molecule is(are) likely to react with a nucleophile such as (CN-)? (62)
    A. II only
    B. III only
    C. I and III
    D. III and IV

  14. Which ion is not aromatic? (68)
    A.
    B.
    C.
    D.

  15. Which choice ranks these compounds from strongest to weakest acid?(11)
    A. 1>3>2>4
    B. 2>4>3>1
    C. 4>2>3>1
    D. 4>3>2>1

  16. Which isomeric alcohol gives rise to this carbon-13 NMR spectrum? (47)
    A. CH3 CH2CH2 CH2OH
    B. CH3 CH2CH(OH) CH3
    C. CH3 CH(CH3) CH2OH
    D. (CH3)33COH

  17. In which reaction is an organic compound oxidized?(55)
    A. CH3CH2O-Na+ + CH3I -->CH3CH2OCH3 + NaI
    B.
    C.
    D.

  18. Which structure is consistent with the proton NMR spectrum? (65)
    A.
    B.
    C.
    D.