An excess of $CH X_{3} MgBr$ in dry ether is added to 1 mol of the compound shown. Count only the acidic hydrogens that are removed as methane: those of $O - H$ groups and of a terminal alkyne $C \equiv C - H$ (ignore any addition of the Grignard reagent to carbonyl groups). How many moles of $CH X_{4}$ are evolved? Answer as an integer.

Numerical answer type, tolerance 0.5.

Answer: 3

The compound is 2-ethynyl-4-hydroxybenzoic acid. Each active hydrogen protonates one CH3MgBr: carboxylic O-H (1), phenolic O-H (1) and the terminal alkyne C-H (1) give 3 mol of CH4 per mole of compound (RDKit count of such hydrogens: 3).

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