(i) Give a reason for each of the following

(a) Ethoxy ethane does not react with sodium, but ethanol does
(b) Ethoxy ethane with conc. HI at 373K gives C2HsOH and CHs3I but not CH₃0H and C₂H₅I.

OR

(ii) An organic compound [A] having molecular formula C₄H₁₀O forms a compound [B] with molecular formula C₄H₈O on oxidation. Compound [B] gives a positive iodoform test. The reaction of compound [B] with CH₃MgBr followed by hydrolysis gives compound [C] with molecular formula C₅H₁₂0.

Identify the compounds [A], [B] and [C]. Write the reaction for the conversion of compound [A] to compound [B].

Solution

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