MolSynapsequestion bank
MolSynapse / Question bank / General Organic Chemistry II: Acids and Bases / Acidic strength of organic compounds and pKa comparisons
JEE Main levelSingle correct optionDifficulty 2 of 3g2021

Which of the following compounds reacts with sodamide () to give a sodium salt with evolution of ammonia?

  1. A
  2. B
  3. C
  4. D

Answer: B

Only a terminal alkyne has an sp-hybridised C-H bond acidic enough (pKa about 25) to be deprotonated by the amide ion (conjugate acid ammonia, pKa 38). But-1-yne gives sodium but-1-yn-1-ide; but-2-yne has no sp C-H, and the alkene and alkane C-H bonds are much less acidic.
Practice General Organic Chemistry II: Acids and Bases More on Acidic strength of organic compounds and pKa comparisons

More questions on Acidic strength of organic compounds and pKa comparisons