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Q7.24 (iv):
Write the names of reagents and equations for the preparation of the following ethers by Williamson’s synthesis: 1-Methoxyethane

Solution :

Step 1: Theoretical Foundation of Williamson’s Synthesis

Williamson’s synthesis is a laboratory method for the preparation of symmetrical and unsymmetrical ethers. It involves the reaction of an alkoxide ion ($RO^-$) acting as a nucleophile with a primary alkyl halide ($R'-X$) via an $S_N2$ mechanism [Per the Mechanism of Nucleophilic Substitution].

The general reaction is: $R-O^-Na^+ + R'-X \rightarrow R-O-R' + NaX$. For the preparation of 1-Methoxyethane ($CH_3-O-CH_2CH_3$), we must choose the combination that avoids competing $E2$ elimination reactions by ensuring the alkyl halide is primary.

Step 2: Selection of Reagents

1-Methoxyethane consists of a methoxy group ($-OCH_3$) and an ethyl group ($-CH_2CH_3$). To optimize yield, the alkyl halide component should be the least sterically hindered species to facilitate the $S_N2$ attack.

  • Option A: Sodium methoxide ($CH_3ONa$) + Chloroethane ($CH_3CH_2Cl$). Preferred because the alkyl halide is primary.
  • Option B: Sodium ethoxide ($CH_3CH_2ONa$) + Chloromethane ($CH_3Cl$). Also feasible, though methyl halides are highly reactive.

Step 3: Chemical Equation

Using Sodium methoxide and Chloroethane:

$CH_3ONa + CH_3CH_2Cl \xrightarrow{\Delta} CH_3-O-CH_2CH_3 + NaCl$

Step 4: Visualizing the $S_N2$ Mechanism

CH₃O⁻ (Nucleophile) CH₃-CH₂-Cl (Electrophile) Transition State: [CH₃O...CH₂CH₃...Cl]⁻ → CH₃-O-CH₂CH₃ + Cl⁻

Step 5: Analytical Summary Table

Component Chemical Formula
Nucleophile (Alkoxide) $CH_3ONa$ (Sodium methoxide)
Electrophile (Alkyl halide) $CH_3CH_2Cl$ (Chloroethane)
Target Ether $CH_3-O-CH_2CH_3$ (1-Methoxyethane)

Final Solution: The preparation of 1-Methoxyethane via Williamson’s synthesis is achieved by reacting sodium methoxide ($CH_3ONa$) with chloroethane ($CH_3CH_2Cl$), resulting in $CH_3-O-CH_2CH_3$ and sodium chloride ($NaCl$).


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