Reacting (2R)−2−pentanol with HBr leads to the formation of equal amounts of (2R)−2−bromopentane and (2S)−2−bromopentane. Draw a stepwise mechanism for the reaction that is consistent with this observation.

Complete the sentences to best explain the ranking. match the words below to the appropriate blanks in the sentences. a less polar bondhigher molar massion-dipole forcesstronger intermolecular forcesdipole-dipole forcesdispersion forceshydrogen bonding1. h2s and h2se exhibit the following intermolecular forces:.2. therefore, when comparing h2s and h2se the one with a has a higher boiling point .3. the strongest intermolecular force exhibited by h2o is . therefore, when comparing h2se and h2o the one with has a higher boiling point.