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Question: Which of following reactions are shown with incorrect major product : $CH_3 - \begin{matrix} CH_3 \...

Which of following reactions are shown with incorrect major product :

CH3−CH3∣C∣CH3−ONa+CH3−Cl⟶CH3−CH3∣C∣CH3−O−CH3CH_3 - \begin{matrix} CH_3 \\ | \\ C \\ | \\ CH_3 \end{matrix} - ONa + CH_3 - Cl \longrightarrow CH_3 - \begin{matrix} CH_3 \\ | \\ C \\ | \\ CH_3 \end{matrix} - O - CH_3

A

CH3−CH3∣C∣CH3−ONa+CH3−Cl⟶CH3−CH3∣C∣CH3−O−CH3CH_3 - \begin{matrix} CH_3 \\ | \\ C \\ | \\ CH_3 \end{matrix} - ONa + CH_3 - Cl \longrightarrow CH_3 - \begin{matrix} CH_3 \\ | \\ C \\ | \\ CH_3 \end{matrix} - O - CH_3

Answer

The product shown in the reaction is the correct major product.

Explanation

Solution

The given reaction is a Williamson Ether Synthesis between sodium tert-butoxide and methyl chloride.

Sodium tert-butoxide is a strong, bulky base. Methyl chloride is a primary alkyl halide. The reaction proceeds via an SN2S_N2 mechanism.

The tert-butoxide ion acts as a nucleophile, attacking the carbon of methyl chloride and displacing the chloride ion.

CH3−CH3∣C∣CH3−O−+CH3−Cl⟶CH3−CH3∣C∣CH3−O−CH3+Cl−CH_3 - \begin{matrix} CH_3 \\ | \\ C \\ | \\ CH_3 \end{matrix} - O^- + CH_3 - Cl \longrightarrow CH_3 - \begin{matrix} CH_3 \\ | \\ C \\ | \\ CH_3 \end{matrix} - O - CH_3 + Cl^-

Elimination (E2E2) is not favored because methyl chloride does not have beta-hydrogens. Therefore, the major product is tert-butyl methyl ether, which matches the product shown.