(a) Propane
"CH"_4 stackrelcolor(blue)("Cl"_2"/hν"color(white)(mm))(→) underbrace("CH"_3"-Cl")_color(red)("chloromethane")
"CH"_3"-Cl" stackrelcolor(blue)("Na/ether"color(white)(mm))(→) underbrace("CH"_3"-CH"_3)_color(red)("ethane") (Wurtz synthesis)
"CH"_3"-CH"_3 stackrelcolor(blue)("Cl"_2"/hν"color(white)(mm))(→) underbrace("CH"_3"CH"_2"-Cl")_color(red)("chloroethane")
"CH"_3"CH"_2"-Cl" stackrelcolor(blue)("Li/ether"color(white)(mm))(→) underbrace("CH"_3"CH"_2"-Li")_color(red)("ethyllithium")
"CH"_3"CH"_2"-Li" stackrelcolor(blue)("CuI"color(white)(mm))(→) underbrace(("CH"_3"CH"_2)_2"CuLi")_color(red)("lithium diethylcuprate") (Corey-House synthesis)
("CH"_3"CH"_2)_2"CuLi" + "CH"_3"-Cl" → underbrace("CH"_3"CH"_2"-CH"_3)_color(red)("propane")
(b) Butane
underbrace("CH"_3"CH"_2"-Cl")_color(red)("chloroethane") stackrelcolor(blue)("Na/ether"color(white)(mm))(→) underbrace("CH"_3"CH"_2"-CH"_2"CH"_3)_color(red)("butane") (Wurtz synthesis)
(c) Methyl Butanoate
underbrace("CH"_3"CH"_2"CH"_3)_color(red)("propane") stackrelcolor(blue)("Cl"_2"/hν"color(white)(mm))(→) underbrace("CH"_3"CH"_2"CH"_2"-Cl")_color(red)("1-chloropropane")
"CH"_3"CH"_2"CH"_2"-Cl" stackrelcolor(blue)("CN"^"-"color(white)(mm))(→) underbrace("CH"_3"CH"_2"CH"_2"-CN")_color(red)("1-butanenitrile")stackrelcolor(blue)(
"CH"_3"CH"_2"CH"_2"-CN" stackrelcolor(blue)("H"_3"O"^"+", Δcolor(white)(m))(→) underbrace("CH"_3"CH"_2"CH"_2"-COOH")_color(red)("butanoic acid")
underbrace("CH"_3"Cl")_color(red)("chloromethane") stackrelcolor(blue)("aq. KOH", Δ color(white)(mm))(→) underbrace("CH"_3"-OH")_color(red)("methanol")
"CH"_3"CH"_2"CH"_2"COOH" + "CH"_3"-OH" stackrelcolor(blue)("H"_3"O"^"+"color(white)(mm))(⇌) underbrace("CH"_3"CH"_2"CH"_2"CO-OCH"_3)_color(red)("methyl butanoate")
(d) Ethanoic acid
underbrace("CH"_3"-Cl")_color(red)("chloromethane") stackrelcolor(blue)("Mg/dry ether"color(white)(mm))(→) underbrace("CH"_3"-MgCl")_color(red)("methylmagnesium chloride")
"CH"_3"-MgCl" stackrelcolor(blue)("1. CO"_2; "2. H"^"+"color(white)(mm))(→) underbrace("CH"_3"-COOH")_color(red)("ethanoic acid") (Grignard synthesis)
(e) Ethanol
underbrace("CH"_3"CH"_2"-Cl")_color(red)("chloroethane") stackrelcolor(blue)("OH"^"-"color(white)(mm))(→) underbrace("CH"_3"CH"_2"-OH")_color(red)("ethanol")
