Question

Show how to convert ethylene to these compounds. (a) Ethane (b) Ethanol (c) Bromoethane (d) 2-Chloroethanol (e) 1,2 -Dibromoethane (f) 1,2 -Ethanediol (g) Chloroethane

Short answer

Question: Describe the reactions necessary to convert ethylene to the following compounds: a) Ethane, b) Ethanol, c) Bromoethane, d) 2-Chloroethanol, e) 1,2-Dibromoethane, f) 1,2-Ethanediol, and g) Chloroethane. Answer: a) Ethane can be formed from ethylene through hydrogenation using hydrogen gas and a catalyst like palladium or platinum. b) Ethanol can be formed from ethylene by oxymercuration-reduction involving water, mercuric acetate, and sodium borohydride. c) Bromoethane can be formed from ethylene through hydrohalogenation using hydrogen bromide. d) 2-Chloroethanol can be formed from ethylene by oxyhalogenation involving water and hydrochloric acid catalyst. e) 1,2-Dibromoethane can be formed from ethylene through halogenation using bromine. f) 1,2-Ethanediol can be formed from ethylene by hydroxylation using osmium tetroxide and sodium bisulfite. g) Chloroethane can be formed from ethylene through hydrohalogenation using hydrogen chloride.

Step-by-step solution

a) Ethane (C2H6)

To convert ethylene to ethane, we need to convert the carbon-carbon double bond of ethylene to a single bond, a reaction known as hydrogenation. This can be achieved by treating ethylene with hydrogen gas (H2) in the presence of a catalyst such as a palladium or platinum. The reaction is as follows: C2H4 + H2 -> C2H6

b) Ethanol (C2H5OH)

To convert ethylene into ethanol, we will use an oxymercuration-reduction mechanism. This involves the addition of water (H2O) and mercuric acetate [Hg(OAc)2] followed by the reduction with sodium borohydride (NaBH4). The reaction is as follows: C2H4 + H2O / Hg(OAc)2 -> C2H5OH / NaBH4

c) Bromoethane (C2H5Br)

We can convert ethylene into bromoethane by reacting it with hydrogen bromide (HBr) in a hydrohalogenation reaction. The reaction is as follows: C2H4 + HBr -> C2H5Br

d) 2-Chloroethanol (C2H4ClOH)

To convert ethylene into 2-chloroethanol, we use the reaction between ethylene and water (H2O) in the presence of a hydrochloric acid (HCl) catalyst. This reaction follows an oxyhalogenation mechanism. The reaction is as follows: C2H4 + H2O / HCl -> C2H4ClOH

e) 1,2-Dibromoethane (C2H4Br2)

To convert ethylene into 1,2-dibromoethane, we utilize a halogenation reaction with bromine (Br2). The reaction is as follows: C2H4 + Br2 -> C2H4Br2

f) 1,2-Ethanediol (C2H4(OH)2)

To convert ethylene to 1,2-ethanediol, we use a hydroxylation mechanism, reacting ethylene with osmium tetroxide (OsO4) followed by sodium bisulfite (NaHSO3). The reaction is as follows: C2H4 + OsO4 -> C2H4(OH)2 / NaHSO3

g) Chloroethane (C2H5Cl)

To convert ethylene into chloroethane, we perform a hydrohalogenation reaction using hydrogen chloride (HCl). The reaction is as follows: C2H4 + HCl -> C2H5Cl