MolSynapsequestion bank
MolSynapse / Question bank / General Organic Chemistry II: Acids and Bases / Most acidic hydrogen in drawn molecules
JEE Advanced levelNumerical answerDifficulty 3 of 3g2256

In the compound shown, count the sets of chemically equivalent hydrogen atoms whose pKa is below 12. Use these approximate values: carboxylic acid O-H 4, phenolic O-H 8 to 10, CH2 flanked by two C=O groups 9 to 11, CH3 of a methyl ketone 20, aromatic C-H above 40. Each set of equivalent hydrogens counts once. Give the answer as an integer.

Numerical answer type, tolerance 0.5.

Answer: 3

Three sets qualify: the COOH hydrogen, the phenolic OH hydrogen (pKa about 9 to 10 even with the ortho acyl group), and the two CH2 hydrogens of the 1,3-diketone unit (pKa about 9 to 10). The CH3 hydrogens (pKa about 20) and the three aromatic hydrogens are not acidic enough. Number = 3.
Practice General Organic Chemistry II: Acids and Bases More on Most acidic hydrogen in drawn molecules

More questions on Most acidic hydrogen in drawn molecules