Outline reaction mechanisms by which ethyne may be converted to; Ethanamide, chloroehtene, Ethane , and Ethanol?
Organic chemistry
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Jan 20
(i) Reaction mechanism for the conversion of ethyne to ethanamide:
Step 1: Protonation of ethyne Ethyne (C2H2) reacts with a strong acid, such as sulfuric acid (H2SO4), to form a protonated ethyne intermediate. C2H2 + H2SO4 → C2H3+ + HSO4-
Step 2: Nucleophilic attack by ammonia Ammonia (NH3) acts as a nucleophile and attacks the protonated ethyne intermediate, forming an imine intermediate. C2H3+ + NH3 → C2H3NH2+
Step 3: Hydrolysis The imine intermediate undergoes hydrolysis in the presence of water (H2O), resulting in the formation of ethanamide (also known as acetamide). C2H3NH2+ + H2O → C2H5CONH2 + H+
(ii) Reaction mechanism for the conversion of ethyne to chloroethene:
Step 1: Chlorination Ethyne (C2H2) reacts with chlorine (Cl2) in the presence of a catalyst, such as iron (Fe), to form 1,2-dichloroethene as an intermediate. C2H2 + Cl2 → C2H2Cl2
Step 2: Dehydrochlorination 1,2-dichloroethene undergoes dehydrochlorination in the presence of a strong base, such as sodium hydroxide (NaOH), to form chloroethene (also known as vinyl chloride). C2H2Cl2 + NaOH → C2H3Cl + NaCl + H2O
(iii) Reaction mechanism for the conversion of ethyne to ethane:
Step 1: Hydrogenation Ethyne (C2H2) reacts with hydrogen gas (H2) in the presence of a catalyst, such as palladium (Pd) or platinum (Pt), to form ethene (C2H4) as an intermediate. C2H2 + H2 → C2H4
Step 2: Hydrogenation Ethene (C2H4) further reacts with hydrogen gas (H2) in the presence of the same catalyst to form ethane (C2H6). C2H4 + H2 → C2H6
(iv) Reaction mechanism for the conversion of ethyne to ethanol:
Step 1: Hydration Ethyne (C2H2) reacts with water (H2O) in the presence of a strong acid catalyst, such as sulfuric acid (H2SO4), to form an enol intermediate. C2H2 + H2O → C2H3OH
Step 2: Tautomerization The enol intermediate undergoes tautomerization, converting it into the more stable keto form, which is ethanol (C2H5OH). C2H3OH → C2H5OH