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Chem 333
Chem 337
Chem Dept

Chemistry 331: Objectives for Exam 2

Go to a summary listing of reactions for Exam 2

You should be able to: 

  1. Nomenclature: Given a structure write the IUPAC name, or given an IUPAC name draw the structure, for any alcohol, alkyl halide, or alkene (including E-Z designation). Radicofunctional nomenclature will not be emphasized. [4.1, 4.2, 5.1, 5.3, 5.4]
  2. Structure-Property Relationships: Predict relative boiling points, solubilities, and stabilities (heats of combustion and hydrogenation) for alcohols, alkyl halides, and alkenes. Know how to predict differences in thermodynamic stabilities of the different types of substituted alkenes. [4.5, 5.5] Recognize the different classes of alkyl halides and alcohols. [4.3]
  3. Mechanisms (Note that mechanisms are very important.)
    1. Write out the steps for the acid-catalyzed SN1 and SN2 mechanisms for reactions of alcohols and predict the relative reactivities of alcohols toward these mechanisms. Use curved arrows. [4.10-4.14]
    2. Write out the steps for the mechanism for free-radical halogenation of alkanes and predict the number of monohalogenated products and relative product distributions in the halogenation of higher alkanes. [4.16-4.20]
    3. Write out the steps for the E1 mechanism for the acid-catalyzed dehydration of alcohols and explain regiochemistry, stereochemistry, and rearrangements in terms of the mechanism. Use curved arrows. [5.10-5.13]
    4. Diagram the E1 and E2 mechanisms for the dehydrohalogenation of alkyl halides and explain the regiochemistry and stereochemistry of the reactions. [5.14-5.17] (The E2 mechanism is more important than the E1 mechanism for alkyl halide eliminations.) Use curved arrows. Note the anti-periplanar orientation needed for the E2 reaction.
    5. Explain regioselectivity and stereoselectivity in electrophilic and free-radical additions to alkenes. [6.6-6.8, 6.15-6.16] (The step-by-step mechanism of peroxide catalyzed addition of HBr to alkenes is not covered for Exam 2.)
    6. Show the mechanism of addition of HX to alkenes, which proceeds by a carbocation intermediate. Be aware of situations where carbocations may rearrange. Use curved arrows.
    7. Write the mechanism of addition of Br2 and Cl2 to alkenes. Know that the important intermediate is a bridged halonium ion (3-membered ring). For halohydrin formation, the mechanism is similar to halogenation except that the halonium ion is attacked by water instead of a halide ion. Both reactions proceed via anti addition. Use curved arrows.
    8. Although the mechanism of hydroboration-oxidation is not covered on Exam 2, you should know that the reaction gives syn addition of water to an alkene and that the addition has anti-Markovnikov regiochemistry.
  4. Reactions: (Categorize these according to type of mechanism.)
    1. Reactions of alcohols
      1. alkyl halides from alcohols and hydrogen halides [4.9]
      2. other methods for converting alcohols to alkyl halides [4.15]
    2. Free-radical halogenation of alkanes [4.20]
    3. Preparation of alkenes
      1. dehydration of alcohols [5.9-5.11]
      2. dehydrohalogenation of alkyl halides [5.14]
    4. Reactions of alkenes
      1. hydrogenation (syn addition of H2) [6.1]
      2. addition of hydrogen halides [6.4] (Markovnikov)
      3. addition of HBr and peroxides [6.8] (anti-Markovnikov)
      4. addition of sulfuric acid and then water [6.9]
      5. hydration using sulfuric acid and water [6.10]
      6. hydroboration-oxidation (syn addition of H2O)[6.11]
      7. addition of halogens (anti addition of X2)[6.14]
      8. halohydrin formation (anti addition of HOX) [6.17]
      9. epoxidation [6.18]
      10. ozonolysis [6.19]

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