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The least acidic among the following compounds

M methyl propiolate, MeO2C-C triple bond C-H; N butanoic acid; O 3-methoxyphenol; P benzenesulfonic acid

is:

  • A.M
  • B.N
  • C.O
  • D.P

Answer: A

The least acidic compound is M, methyl propiolate.

Its only acidic hydrogen is the terminal alkyne C-H. Even with the ester pulling electron density, removing it leaves the negative charge on carbon, so it is a far weaker acid than any of the O-H acids here.

The others are all O-H acids whose conjugate bases put the charge on oxygen: 3-methoxyphenol (O) has pKa about 10, butanoic acid (N) about 4.8, and benzenesulfonic acid (P), whose anion is spread over three oxygens, is a strong acid with a negative pKa. So the acid strength order is P \(\gt\) N \(\gt\) O \(\gt\) M.

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