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Q6.19(xi):
How the following conversions can be carried out? (xi) Ethyl chloride to propanoic acid

Solution :

Step 1: Conversion of Ethyl Chloride to Propyl Nitrile

The conversion of $CH_3CH_2Cl$ (ethyl chloride) to $CH_3CH_2CN$ (propanenitrile) is achieved via a nucleophilic substitution reaction [Per the $S_N2$ mechanism]. Ethyl chloride is reacted with potassium cyanide ($KCN$) in an aqueous alcoholic medium.

Reaction:
$CH_3CH_2Cl + KCN_{(alc)} \rightarrow CH_3CH_2CN + KCl$

[Justification: The cyanide ion ($CN^-$) acts as an ambident nucleophile, attacking the electrophilic carbon attached to the chlorine atom, resulting in the elongation of the carbon chain by one carbon atom.]

Step 2: Hydrolysis of Propanenitrile to Propanoic Acid

The nitrile functional group ($R-CN$) undergoes complete acid-catalyzed hydrolysis to form a carboxylic acid. Propanenitrile is treated with water in the presence of a strong mineral acid (like $H_2SO_4$ or $HCl$) or a strong base followed by acidification.

Reaction:
$CH_3CH_2CN + 2H_2O + H^+ \xrightarrow{\Delta} CH_3CH_2COOH + NH_4^+$

[Justification: The $C\equiv N$ triple bond is polarized. The nucleophilic attack of water on the carbon atom, followed by sequential proton transfers and the loss of ammonia ($NH_3$), converts the cyanide group into a carboxylic acid group ($COOH$).]

Summary of Reaction Pathway

Stage Reactant/Condition Product
1. Nucleophilic Substitution $CH_3CH_2Cl + KCN$ $CH_3CH_2CN$
2. Acidic Hydrolysis $CH_3CH_2CN + H_3O^+ / \Delta$ $CH_3CH_2COOH$
$CH_3CH_2Cl$ $KCN(alc)$ $CH_3CH_2CN$ $H_3O^+ / \Delta$ $CH_3CH_2COOH$

Final Solution: The conversion of ethyl chloride to propanoic acid is performed in two steps: first, nucleophilic substitution with $KCN$ to yield propanenitrile, followed by complete acidic hydrolysis to yield propanoic acid ($CH_3CH_2COOH$).


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