2 thoughts on “What Reaction(s) Should Come First?

  1. I am also starting my discussion of reactivity with substitution and elimination, partly because of the wide applicability of nucleophilic substitution. For instance, it had always occurred to me that it would be natural to introduce the Williamson ether synthesis when discussing SN2 reactions. Other examples I’m covering include epoxide reactions, acetylide alkylation and enolate alkylation.

    1. Jeremy,

      What you describe is exactly why I thought it made so much sense to me. After I give students a solid foundation for working with multistep mechanisms, I teach the SN1/SN2/E1/E2 competition, and then I cover relatively extensively how those reactions are applied in useful ways. The outline of my coverage of that material is below and, as you can see, it hits those reactions you mentioned.

      1. NUCLEOPHILIC SUBSTITUTION: Converting alcohols to alkyl halides using PBr3 and PCl3
      2. NUCLEOPHILIC SUBSTITUTION: Alkylation of ammonia and amines
      3 NUCLEOPHILIC SUBSTITUTION: Alkylation of alpha carbons
      4. NUCLEOPHILIC SUBSTITUTION: Halogenation of alpha carbons
      5. NUCLEOPHILIC SUBSTITUTION: Diazomethane formation of methyl esters
      6. NUCLEOPHILIC SUBSTITUTION: Formation of ethers
      7. NUCLEOPHILIC SUBSTITUTION: Epoxides and oxetanes as substrates
      8. ELIMINATION: Generating alkynes via elimination reactions
      9. ELIMINATION: Hofmann elimination

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