In a Zerewitinoff-type analytical determination, of pure methanol () reacts completely with an exces — Alcohols Phenols and Ethers Chemistry Question
Question
In a Zerewitinoff-type analytical determination, $1 \text{ mole}$ of pure methanol ($CH_3OH$) reacts completely with an excess of methylmagnesium iodide ($CH_3MgI$). Exactly how many moles of methane gas ($CH_4$) will be evolved?
💡 Solution & Explanation
Grignard reagents act as exceptionally strong bases in the presence of acidic protons. The slightly acidic proton of the hydroxyl group in methanol immediately reacts with the methyl carbanion equivalent of the Grignard reagent: $CH_3MgI + CH_3OH \rightarrow CH_4 \uparrow + CH_3OMgI$. One mole of methanol contains one acidic proton, yielding exactly one mole of methane gas.