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- Can you help select the best reagent for the transformation below?Following are the steps in one of the several published syntheses of frontalin, a pheromone of the western pine beetle. (a) Propose reagents for Steps 18. (b) Propose a mechanism for the cyclization of the ketodiol from Step 8 to frontalin.Propose a mechanism for this isomerization.
- Provide the mechanism and products for the acid-catalyzed epoxide opening reactions below, including appropriate stereochemistry.Solvolysis of the following bicyclic compound in acetic acid gives a mixture of products, two of which are shown. The leaving group is the anion of a sulfonic acid, ArSO3H. A sulfonic acid is a strong acid, and its anion, ArSO3, is a weak base and a good leaving group. Propose a mechanism for this reaction.Knoevenagel condensation is a reaction involving an active methylene compound (a CH2 flanked by two electron-withdrawing groups) and an aldehyde and ketone. Propose a mechanism for the reaction below.
- The Meerwein-Ponndorf-Verley reaction involves reduction of a ketone by treatment with an excess of aluminum triisopropoxide, [(CH3)2CHO]3Al. The mechanism of the process is closely related to the Cannizzaro reaction in that a hydride ion acts as a leaving group. Propose a mechanism.Use your general knowledge of alkene chemistry to suggest a mechanism for the following reaction.Draw the structures of the organoboranes formed when borane reacts with each alkene below, including the regiochemistry and stereochemistry as appropriate. Propose a mechanism for each reaction.