How will you convert methane to the following: (a) propane (b) butane (c) methyl butanoate (d) ethanoic acid (e) ethanol?

Question

Isabella Acosta · Accepted Answer

Warning! Long Answer. Here are some possibilities.

(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) Propane #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) Methyl Butanoate (c) #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) Acid ethanol #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) Alcohol #underbrace("CH"_3"CH"_2"-Cl")_color(red)("chloroethane") stackrelcolor(blue)("OH"^"-"color(white)(mm))(→) underbrace("CH"_3"CH"_2"-OH")_color(red)("ethanol")#

Sarah Angotti · Answer

undefined (a) Propane: By subjecting methane to a dehydrogenation process, followed by oligomerization.

(b) Butane: Achieved through the dehydrogenation of methane, leading to ethylene, which is then oligomerized to form butanes.

(c) Methyl Butanoate: Methane is converted to methanol via steam reforming, and then methanol is esterified with butanoic acid.

(d) Ethanoic Acid: Methane is first converted to synthesis gas (a mixture of carbon monoxide and hydrogen), followed by carbonylation to produce acetic acid, which is subsequently converted to ethanoic acid.

(e) Ethanol: Methane undergoes steam reforming to produce synthesis gas, which is then converted to ethanol through a series of catalytic reactions.

Delilah Anderson · Answer

undefined (a) To convert methane to propane, you can use a series of chemical reactions known as the propane synthesis process. This process involves several steps, including steam reforming of methane to produce synthesis gas (a mixture of hydrogen and carbon monoxide), followed by the Fischer-Tropsch synthesis to convert the synthesis gas into longer-chain hydrocarbons, including propane.

(b) Similar to the conversion to propane, methane can be converted to butane through the propane synthesis process, but the process would need to be extended to produce even longer hydrocarbon chains, including butane.

(c) To convert methane to methyl butanoate, you would need to start by converting methane to methanol, using a process such as steam reforming followed by synthesis gas conversion to methanol. Then, methanol can undergo esterification with butanoic acid to produce methyl butanoate.

(d) Methane can be converted to ethanoic acid through several steps. First, methane can be converted to methanol via steam reforming and synthesis gas conversion. Then, methanol can be further oxidized to formaldehyde, followed by oxidation to formic acid and then to ethanoic acid.

(e) To convert methane to ethanol, you would first need to convert methane to synthesis gas using steam reforming. Then, the synthesis gas can undergo catalytic hydrogenation to produce ethanol.

It's important to note that these conversion processes often involve multiple steps and specific reaction conditions, and they may require catalysts to facilitate the reactions. Additionally, the efficiency and feasibility of each conversion route can vary depending on factors such as cost, availability of raw materials, and desired product purity.