In addition to more highly chlorinated products, chlorination of butane yields a mixture of compounds with the

Question:

In addition to more highly chlorinated products, chlorination of butane yields a mixture of compounds with the formula C4H9Cl.

(a) Taking stereochemistry into account, how many different isomers with the formula C4H9Cl would you expect?
(b) If the mixture of C4H9Cl isomers were subjected to fractional distillation (or gas chromatography), how many fractions (or peaks) would you expect?
(c) Which fractions would be optically inactive?
(d) Which fractions could theoretically be resolved into enantiomers?
(e) Predict features in the 1H and 13C DEPT NMR spectra for each that would differentiate among the isomers separated by distillation or GC.
(f) How could fragmentation in their mass spectra be used to differentiate the isomers?