How will you bring about the following conversion?

Ethanol to ethyl fluoride

Arrange the compounds of each set in order of reactivity towards ${\mathrm{S}}_{\mathrm{N}}2$ displacement:

$2$-Bromo-$2$-methylbutane, $1$-Bromopentane, $2$-Bromopentane.

How the following conversions can be carried out?

Toluene to benzyl alcohol

How the following conversion can be carried out?

2-Bromopropane to 1-Bromopropane