Organic Chemistry — Question 4

(a) Ethanoic acid to ethyl ethanoate. :

$\underset{\text{ethyl alcohol}}{\text{C}_2\text{H}_5\text{OH}} + \underset{\text{acetic acid}}{\text{CH}_3\text{COOH}} \xrightarrow{\text{Conc. H}_2\text{SO}_4} \underset{\text{ethyl ethanoate}}{\text{CH}_3-\text{COO}-\text{C}_2\text{H}_5} + \text{H}_2\text{O}$

(b) Ethyne is formed

$\underset{\text{calcium carbide}}{\text{CaC}_2} + \underset{\text{water}}{2\text{H}_2\text{O}} \longrightarrow \underset{\text{ethyne [acetylene]}}{\text{C}_2\text{H}_2} + \text{Ca(OH)}_2$

(c) Sodium ethanoate to methane

$\underset{\text{sodium acetate}}{\text{CH}_3\text{COONa}} + \underset{\text{sodalime}}{\text{NaOH}} \xrightarrow[\Delta]{\text{CaO}} \underset{\text{methane}}{\text{CH}_4} + \text{Na}_2\text{CO}_3$

(d) By boiling ethyl chloride with aqueous NaOH.

$\underset{\text{ Chloroethane [ethyl chloride]}}{\text{C}_2\text{H}_5\text{-Cl}} + \text{NaOH [aq.]} \xrightarrow{\text{boil}} \underset{\text{ Ethanol [ethyl alcohol]}}{\text{C}_2\text{H}_5\text{OH}} + \text{NaCl}$

(e) By boiling ethyl chloride with alcoholic KOH.

$\underset{\text{ Chloroethane [ethyl chloride]}}{\text{C}_2\text{H}_5\text{-Cl}} + \underset{\text{ alcoholic KOH}}{\text{KOH [aq.]}} \xrightarrow{\text{boil}} \underset{\text{ Ethene [ethylene]} }{\text{C}_2\text{H}_4} + \text{KCl} +\text{H}_2\text{O}$

(f) Ethene is absorbed in conc. sulphuric acid at 80 °C under 30 atmos. to give ethyl hydrogen sulphate, which on hydrolysis with steam gives ethanol.

$\underset{\text{ Ethene} }{\text{C}_2\text{H}_4} + \underset{\text{conc.}}{\text{H}_2\text{SO}_4} \underset{30 \text{ atmos.}}{\xrightarrow{80 \degree \text{C}}} \underset{\text{ Ethyl hydrogen sulphate} }{\text{C}_2\text{H}_5\text{-HSO}_4}$

$\underset{\text{ Ethyl hydrogen sulphate }}{\text{C}_2\text{H}_5\text{-HSO}_4} + \underset{\text{steam}}{\text{H}_2\text{O}} \longrightarrow \underset{ \text{ Ethanol [ethyl alcohol]} }{\text{C}_2\text{H}_5\text{-OH}} + \text{H}_2\text{SO}_4$

(g) By heating ethyl alcohol with concentrated H₂SO₄ at 170°C.

$\underset{\text{ ethyl alcohol}}{\text{C}_2\text{H}_5\text{OH}} \xrightarrow[170\degree\text{C}]{\text{Conc. H}_2\text{SO}_4\text{[excess]}} \underset{ \text{ethene}}{\text{C}_2\text{H}_4} + \text{H}_2\text{O}\$