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Q6.19(xvii):
How the following conversions can be carried out? (xvii) Chloroethane to butane

Solution :

Step 1: Chemical Transformation Identification

The conversion of chloroethane ($CH_3CH_2Cl$) to butane ($CH_3CH_2CH_2CH_3$) requires the doubling of the carbon chain length. This type of transformation is characteristic of the Wurtz Reaction, which utilizes sodium metal to couple two alkyl halide molecules. [Per the mechanism of the Wurtz Reaction, an alkyl halide reacts with sodium in the presence of dry ether to form a symmetrical alkane].

Step 2: Chemical Equation and Mechanism

The reaction involves the following stoichiometry:

$2CH_3CH_2Cl + 2Na \xrightarrow{\text{dry ether}} CH_3CH_2CH_2CH_3 + 2NaCl$

The mechanism proceeds via the formation of an alkyl sodium intermediate followed by a nucleophilic substitution (coupling):

  • $CH_3CH_2Cl + 2Na \rightarrow CH_3CH_2Na + NaCl$
  • $CH_3CH_2Na + CH_3CH_2Cl \rightarrow CH_3CH_2CH_2CH_3 + NaCl$

Step 3: Schematic Representation

2 CH₃CH₂Cl 2Na / Dry Ether CH₃CH₂CH₂CH₃ + 2NaCl

Step 4: Experimental Considerations

Parameter Specification
Reagent Metallic Sodium ($Na$)
Solvent Anhydrous (Dry) Ether
By-product Sodium Chloride ($NaCl$)
Yield Note High yields are typically obtained for symmetrical alkanes like butane due to the absence of mixed product formation.

Final Solution: The conversion of chloroethane to butane is achieved by treating two equivalents of chloroethane with sodium metal in the presence of dry ether, resulting in the coupling of the ethyl groups to form butane via the Wurtz Reaction: $2CH_3CH_2Cl + 2Na \xrightarrow{\text{dry ether}} CH_3CH_2CH_2CH_3 + 2NaCl$.


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