Compound X is treated as shown : X NaHC O 3 A ( gas ) + B ; B C H 3 MgBr ( excess ) C ( gas ) + D The sum of the molecular masses of the gases A and C is (an integer):

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Compound X is treated as shown : X NaHC O 3 ​ ​ A ( gas ) + B ; B C H 3 ​ MgBr ( excess ) ​ C ( gas ) + D The sum of the molecular masses of the gases A and C is (an integer):

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Only the –COOH group of X ( p K a ​ about 4) is acidic enough to react with NaHC O 3 ​ : A = C O 2 ​ (44) and B is the sodium carboxylate. The phenol and the terminal alkyne do not react with NaHC O 3 ​ . Excess C H 3 ​ MgBr (dry) takes up the remaining active hydrogens, the phenolic O − H and the terminal ≡ C − H , and releases methane: C = C H 4 ​ (16). Sum = 44 + 16 = 60. Answer: 60.

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