Answer to Question #348075 in Organic Chemistry for Rzf

Question

Why phenol is much stronger acid than 2,6 di tert butyl phenol ? Explain

Answer 1

The solvation effect is a reason for the difference between the acidity of phenol and 2,6-Di-tert-butylphenol. The conjugate base of phenol can be easily stabilized by solvent molecules. Simultaneously, the conjugate base of 2,6-Di-tert-butylphenol is sterically hindered by two methyl groups, and such stabilization is much weaker in this case.

Therefore conjugate base of phenol is much more stable than the conjugate base of 2,6-Di-tert-butylphenol. The more stable the conjugate base, the stronger the acid. For that reason, phenol is a stronger acid than 2,6-Di-tert-butylphenol.