The reaction of 1 -chlorobutane with sodium hydroxide to give 1 -butanol is catalyzed by sodium iodide.
a. Work out the stereochemistry to be expected for both the catalyzed and the uncatalyzed reactions if [tex]\ \textless \ [/tex] smiles [tex]\ \textgreater \ \mathrm{CCCC}(\mathrm{C}(=\mathrm{O}) \mathrm{Cl}) \mathrm{c1ccccc}\space 1\ \textless \ [/tex] smiles [tex]\ \textgreater \ [/tex] (optically active) were used as the starting material. Show your reasoning.
b. Does retention of configuration, as the overall result of an [tex]\mathrm{S}_{\mathrm{N}} 2[/tex], automatically preclude operation of the usual mechanism? Explain.