Solving mechanism problems is not a matter of remembering particular mechansms and particular compounds. A logical series of steps can be followed:
- Analyze the transformation: define the correlations between reactants and products.
- Identify stereoelements and possible stereochemical outcomes; that is, determine if your mechanism must explain a stereochemical event, and if so, what it is.
- If necessary after the analysis of (B), draw clear stereoprojections of reactants and products.
- Identify the fundamental mechanistic class or classes of the reaction. Only ten classes exist.
- For pericyclic processes, identify and draw the frontier orbitals or the fully interacting basis sets. Proceed to determine the feasibility of the process.
- For all other reactions, write the mechanism as a series of elementary processes.
- Elementary processes are reaction steps that proceed through single transition states; for heterolytic reactions they are always Bronsted or Lewis acid-base reactions.
- To keep track of bond making and breaking, use curly arrows or fishhooks.
- Curly arrows are for heterolytic processes and the arrowheads have two barbs.
- Fishhooks are for homolytic processes; the fishhook has but a single barb.
Some pitfalls:
- The problem doesn't tell us that the given product is not the only product, or is perhaps a minor product
- Information about conditions and reagents may not be complete
- Stereochemical information may be incomplete
This is where experience comes in.