JEE Main · 2020 · 03 Sep 2020 · Shift 1 · General Organic Chemistry

Which one of the following compounds possesses the most acidic hydrogen?

(A) $H_{3} C - C \equiv C - H$
(B)(see structure)
✓ Correct
(C)(see structure)
(D)(see structure)

Answer: (B)

Solution

The acidity of a hydrogen is set by how well the anion left behind is stabilised, and electron-withdrawing groups acting through inductive and resonance effects do this strongly. The compound whose

C H_{2}

is flanked by three ester groups lets the resulting carbanion spread its charge over all three

- COOC H_{3}

units, giving the most stabilised anion and hence the most acidic hydrogen of the set.

JEE Main · 2020 · 03 Sep 2020 · Shift 1 · Single correct option

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