Chapter FRP, Problem 38P

In addition to more highly fluorinated products, fluorination of 2-methylbutane yields a mixture of compounds with the formula $C_5{H}_{11}F$.

(a) How many different isomers with the formula $C_5{H}_{11}F$ would you expect to be produced, taking stereochemistry into account?

(b) If the mixture of $C_5{H}_{11}F$ isomers were subjected to fractions distillation, bow many fractions would you expect to obtain?

(c) Which fractions would be optically inactive?

(d) Which would you be able to resolve into enantiomers?