Question:hard

The correct gas phase acidity order for alcohols \(FCH_2OH\), \(CH_3OH\), \(ClCH_2OH\) and \(BrCH_2OH\) is

Show Hint

In gas phase acidity, conjugate base stabilization depends not only on inductive effect but also on polarizability of the substituent.
Updated On: Jun 5, 2026
  • \(ClCH_2OH > BrCH_2OH > CH_3OH > FCH_2OH\)
  • \(FCH_2OH > BrCH_2OH > ClCH_2OH > CH_3OH\)
  • \(CH_3OH > FCH_2OH > BrCH_2OH > ClCH_2OH\)
  • \(ClCH_2OH > BrCH_2OH > FCH_2OH > CH_3OH\)
Show Solution

The Correct Option is B

Solution and Explanation

Step 1: Frame the comparison.
Acidity here means how easily $X\!-\!CH_2OH$ gives up its proton. Anything that steadies the resulting $RO^-$ makes the acid stronger.

Step 2: Start with methanol.
The $CH_3$ group pushes electron density toward the oxygen, which makes $CH_3O^-$ less stable. So plain methanol is the weakest acid of the set.

Step 3: Add the halogen pull.
A halogen on the carbon drains electron density away and spreads the negative charge, steadying the anion. So all three halo-alcohols beat methanol.

Step 4: Order the halogens in the gas phase.
Here size and polarizability help share the charge. Fluorine's strong electron withdrawal puts $FCH_2OH$ on top, and bromine's bigger, softer cloud handles the charge better than chlorine, so Br comes before Cl.

Step 5: Answer.
The order is \[ \boxed{FCH_2OH > BrCH_2OH > ClCH_2OH > CH_3OH} \]
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