a) Why does this reaction not invert stereochemistry? Explain your answer using the example substrate shown to the right:
(hint: there is an SN2 reaction going on here, but the electrophile is not a carbon atom...)
b) Design a reaction sequence whereby (S)-3-hexanol is converted to (R)-3-chlorohexane in two steps.
c) Draw the products and complete arrow-pushing mechanism for the reaction that would occur if you tried to use HCl to catalyze this substitution reaction.
d) Which reaction is better for producing (R)-3-chlorohexane, the one from part (b) or the one from part (c)? Why?