Consider the monochlorination of 2-methylbutane. (a) Assuming that the product mixture was subjected to fractional distillation, which

Question:

Consider the monochlorination of 2-methylbutane.

(a) Assuming that the product mixture was subjected to fractional distillation, which fractions, if any, would show optical activity?
(b) Could any of these fractions be resolved, theoretically, into enantiomers?
(c) Could the components of each fraction from the distillation be identified on the basis of 1H NMR spectroscopy? What specific characteristics in a 1H NMR spectrum of each fraction would indicate the identity of the component(s) in that fraction?