Which Is The Most Acidic Proton In The Following Compound

Agustus 29, 2022

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The hydrogen of phenol and substituted phenols are acidic in general. Acidity, is roughly a measure of the ease with which the compound (s) lose a proton. Hence, the compound which gives the most stable conjugate base will be the most acidic. Methyl groups tend to increase the electron density of the ring by hyperconjugation.

Proton (a) is the most acidic. Proton (a) is part of a protonated n so pka ≈ 9. Proton (b) is part of an alcohol so pka ≈ 16. Protons (c) are bonded to sp3 carbons so pka ≈ 50 **. This guess is a bit off for the four protons adjacent to the c=o. The functional groups that show − i effect increase the acidity of the compound. Fluorine f shows maximum − i inductive effect among halogens. Therefore f substituted alcohol is more acidic than i substituted. The effectiveness of substituted f increases with the decrease in distance from hydroxylic proton.