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Problem :

Sketch the reaction coordinate vs. energy diagram of the following unimolecular reaction. Reactant A is solvated to carbocation B. Then carbocation B rearranges to carbocation C. Finally the solvent reacts with carbocation C to form product D

Remember that:
  • the initial carbocation formation is the rate-limiting step.
  • carbocations are very unstable (high energy)
  • carbocations rearrange to increase stability

Problem : Predict all possible SN1 and E2 products.

Problem : A sample of this molecule is 100% "S."

Predict its stereochemistry after a predominantly SN1 reaction.

A SN1 reaction on an enantiomeric α-carbon creates a racemate**. Thus there will be equal amounts of "S" and "R" nucleophilic substitution product.