The IUPAC name

  1. The IUPAC name for the following compounds: (3 pts)
  2. Using cis/trans prefixes as appropriate, give the IUPAC names for the following: (3 pts)
  3. Starting with CnH2n+2, derive the general formula for the compounds shown: (3 pts)
  4. Determine the degree of unsaturation for the each of the compounds shown below. (3 pts)
    (a) C9H11Cl5O2 (b) C10H12Br2N4
  5. Using appropriate E/Z prefixes, write the correct IUPAC names for the following compounds: (3 pts)
  6. Draw structural formulas for the following compounds: (3 pts)
    (a) (2Z,4Z)-2,4-dibromo-3-methylhepta-2,4-diene
    (b) ((2E,4Z)-2-bromo-3,5-dichloro-4-methylhexa-2,4-diene
  7. Classify the following carbocations as primary, secondary, tertiary, methyl, or vinyl carbocations as applicable: (3 pts)
  8. Classify the following compounds as E/Z- structures: (3 pts)
  9. Classify each of the following compounds as a cis-trans structure. Write NA if the compound cannot exist be classified as cis or trans. (4 pts)
  10. Rank the following alkenes in order of increasing stability (least to most stable): (3 pts)
  11. Rank the following carbocations in order of increasing stability: (3 pts)
  12. Classify each of the following species as a nucleophile or an electrophile: (4 pts)
  13. Rank the following free radicals in order of increasing stability: (3 pts)
  14. Rank the following carbanions in order of increasing stability: (3 pts)
  15. Which of the following carbocations are likely to rearrange by a 1,2-hydride or a 1,2-methyl shift? (3 pts)
  16. Consider the energy diagrams (I, II, and III) for the three different reactions shown below when answer questions 18(a) – (f). Write NA if an applicable answer is not given. (6 pts)

(a) Which diagram if any represents the slower endergonic reaction? _
(b) Which diagram if any represents the faster endergonic reaction? __

(c) Which diagram if any represents the slower exergonic reaction? _
(d) Which diagram if any represents a faster exergonic reaction? ___

(e) Which reaction has the lowest activation energy?
(f) Based on the energy diagrams, which reaction leads to the least stable product?

(g) Based on the energy diagrams, which reactant is thermodynamically least stable? __

(h) Based on the energy diagrams, which product is thermodynamically most stable? _

  1. Consider the energy diagram shown below when answer questions 19 (a) – (f). (6 pts)