Chapter 12.2, Problem 6ATS

Interpretation Introduction

Interpretation:

An explanation for difference in acidity between given hydroxyl groups in naringenin has to be provided.

Concept Introduction:

Factors affecting acidity of alcohol:

• Resonance is the most important factor affecting acidity. An alcohol with more resonance structures is more stabilized which becomes weak base and strong acid.
• An alcohol attached with more electron withdrawing groups easily loses proton and produces stable conjugate base.
• An alcohol with more steric hindrance does not solvate well and becomes less stable conjugate base.  Alcohol with more solvation is more stable and gives stable conjugate base, which is strong acid.