Chapter 10, Problem 10.49P

Interpretation Introduction

Interpretation:

Phenol is considerably stronger acid than cyclohexanol; the reason has to be proposed.

Concept Introduction:

Base and its conjugate Acid: A Base is a species that can gain a proton. When a base gains a proton $\left({\text{H}}^{\text{+}}\right)$, it forms its conjugate acid. In order to gain a proton, a base must possess lone pair that it can use to form a new bond with the proton. Neutral base forms a positively charged conjugate acid, whereas a positively charged base forms a neutral conjugate acid.

Electron delocalization stabilizes base: If a base has delocalized electrons, then the negative charge that results when the base’s conjugate acid loses a proton will belong to one atom. If a base has delocalized electrons, then the negative charge that results when the base’s conjugate acid loses a proton will be shared by two or more atoms. A base with delocalized electron is more stable than a similar base with localized electrons.

Effect of hybridization on Acidity: The electronegativity of an atom depends on its hybridization.

The stronger acid will have its proton attached to the more electronegative atom.