1. Arrange the following in increasing order of acidity with suitable explanation. ClCH2COOH, BrCH2COOH, ICH2COOH, FCH2COOH
Question
Arrange the following in increasing order of acidity with suitable explanation.
- ClCH2COOH
- BrCH2COOH
- ICH2COOH
- FCH2COOH
Solution
The acidity of a molecule is determined by the stability of its conjugate base. In this case, the conjugate base is the carboxylate anion (RCOO-). The more stable the conjugate base, the more acidic the original molecule.
The stability of the carboxylate anion is increased by electron-withdrawing groups, which help to disperse the negative charge. In this case, the halogens (Cl, Br, I, F) are the electron-withdrawing groups.
The strength of the electron-withdrawing effect decreases down the group (F > Cl > Br > I). Therefore, the acidity of the molecules decreases in the same order: FCH2COOH > ClCH2COOH > BrCH2COOH > ICH2COOH.
So, the increasing order of acidity is: ICH2COOH < BrCH2COOH < ClCH2COOH < FCH2COOH.
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