SMIRKS Practice

Write SMIRKS for each of the transforms described below. Note that answers may not be uniquely correct.

  1. Acid Dissociation: Produce hydronium cations (H30+) plus the appropriate anions from water and an acid ( either hydrochloric, sulfuric, or a carboxylic acid).
  3. Reduction of Nitriles to Amines: Produce primary amines from the corresponding nitriles (e.g. using Lithium Aluminum Hydride followed by acid).
  5. Partial Reduction of Nitriles to Aldehydes: Produce aliphatic aldehydes from aliphatic nitriles (e.g. using Diiso-Butyl Aluminum Hydride).
  7. Grignard Reactions: React alkyl bromides or iodides with carbonyl-containing compounds to produce the corresponding aldehyde, ketone, or carboxylic acid.
  9. Dehydrogenation: Perform dehydrogenation of alkenes to produce alkynes (e.g. via halide addition and double dehydrohalogenation with a strong base).
  11. Keto-Enol Tautomerization: Convert enols (vinyl alcohols) into the corresponding ketone or aldehyde.
  13. Cis Hydrogenation of Alkynes: Hydrogenate alkynes to produce only cis alkenes (e.g. using the Lindlar Catalyst).
  15. Tetrahedral Stereocenter Inversion: Perform a displacement reaction (nucleophylic substitution) of a mono-halogenated tetrahedral center with a carboxylate ion. The products should be a molecule with an inverted stereo center plus a halide anion.
  17. Stereo Retention: Perform a ring opening of a cyclic anhydride using Acephenone ( c1ccccc1C(=O)C ) to produce a 1,3 diketone. Be sure that all products have the same E/Z configuration as the original anhydrides.