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PRACTICE PROBLEM 6.6 SN2 reactions that involve substitution at 1 chirality center can be used to relate the configuration of one molecule to another; because we know the SN2 reaction will occur with inversion. (a) 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 HO (−)-2-Butanol [α] = +36.00 [α] = -13.52 (Enantiomerically pure) (Enantiomerically pure) (b) When 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 minus optical rotation. What is the configuration of (−)-2-iodobutane? Of (+)-2-iodobutane?

          PRACTICE PROBLEM 6.6 SN2 reactions that involve substitution at 1 chirality center can be used to relate the configuration of one molecule to another; because we know the SN2 reaction will occur with inversion. (a) 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 HO (−)-2-Butanol [α] = +36.00 [α] = -13.52 (Enantiomerically pure) (Enantiomerically pure) (b) When 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 minus optical rotation. What is the configuration of (−)-2-iodobutane? Of (+)-2-iodobutane?

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