(Solution) - SN2 reactions that involve breaking a bond to a chirality -(2025 Original AI-Free Solution)

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Academic Level: Undergrad. (yrs 3-4)

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SN2 reactions that involve breaking a bond to a chirality center can be used to relate configurations of molecules because the stereochemistry of the reaction is known.
(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.]

SN2 reactions that involve breaking a bond to a chirality
(b) When optically 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 rotation.
What is the configuration of (-)-2-iodobutane? Of (+)-2-iodobutane?