Organic Chemistry Exam Questions

Chapter 6: Ionic Reactions

  • Know the properties of alkyl halides
  • Understand SN1, and SN2 reactions, and know how to write out the mechanism (curved arrows, intermediates, etc) for a given reaction that falls into one of these categories.
  • Understand the kinetics (1st order or 2nd order) of SN1 and SN2 reactions
  • Understand carbocation structure and stability.
  • Understand transition state theory and be able to sketch free energy diagrams and transition states for given reactions. Understand the difference between exergonic and endergonic. Be familiar with the Hammond-Leffler postulate.
  • Understand how the nature of the leaving group, substrate, nucleophile (base), solvent and temperature can affect substitution reactions. Be familiar with various nucleophiles and solvents discussed in lecture.
  • Understand stereochemistry of substitution reactions
  • Be able to predict the major product(s) of a given reaction, and be able to determine which mechanism (SN1 or SN2) leads to its formation.





Chapter 7: Alkenes and Alkynes I

  • Understand the kinetics (1st order or 2nd order) and mechanisms of E1 and E2 reactions.
  • Be able to predict the major product(s) of a given reaction, and be able to determine which mechanism (SN1, SN2, E1 or E2) leads to its formation.
  • Know physical properties of alkenes, cycloalkenes and alkynes. Understand relative stability of alkenes.
  • Be able to name alkenes using the EZ system of nomenclature
  • Dehydrohalogenation: Know this reaction, stereochemistry and mechanism, and be able to predict the major product that would be formed with a given set of conditions and reactants. Understand dehydrohalogenation on cyclohexane rings.
  • Know Zaitzev’s rule and be able to identify the Zaitzev product and Hofmann product for a given reaction. Also, be able to predict which of these would be the major product in a given reaction.
  • Acid-catalyzed dehydration of alcohols: Know this reaction and possible mechanisms (E1 or E2)
  • Understand carbocation rearrangements and be able to write mechanisms for these types of reactions.
  • Understand the synthesis of alkynes by elimination reactions of vicinal dibromides
  • Understand acidity and reactivity of terminal alkynes
  • Understand hydrogenation of alkenes and alkynes (know the various reagents and catalysts discussed in lecture, and the types of products formed in each case).
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