PROBLEM 6.6: Reactions that involve substitution at a chiral center can be used to relate the configuration of one molecule to another, because we know that the SN2 reaction will occur with inversion. Illustrate how this is true by assigning R,S configurations to the 2-chlorobutane enantiomers based on the following data: [The configuration of (−)-2-butanol is given in Section 5.8C.] (+)-2-Chlorobutane (−)-2-Butanol 872 [α]D +36.00 [α]D -13.52 (Enantiomerically pure) (Enantiomerically pure)
(6) When an enantiomerically pure (+)-2-chlorobutane is allowed to react with potassium iodide in acetone in an SN2 reaction, the 2-iodobutane that is produced has a negative optical rotation. What is the configuration of (−)-2-iodobutane? What is the configuration of (+)-2-iodobutane?