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Chapter 15: Problem 17

Phenols made by the Sandmeyer reaction can be used further in synthesis. Explain why phenol \(\left(\mathrm{p} K_{\Delta}=10\right)\) is easier to deprotonate than cyclohexanol \(\left(\mathrm{p} K_{\mathrm{a}}=16\right)\).

Short Answer

Expert verified
Phenol is easier to deprotonate because it has a lower pKa and its conjugate base is stabilized by resonance.

Step by step solution

01

Understand pKa Values

The pKa value measures the acidity of a compound. Lower pKa values indicate stronger acids, meaning the compound can donate its proton more easily.
02

Compare pKa Values of Phenol and Cyclohexanol

Phenol has a pKa of 10, while cyclohexanol has a pKa of 16. Since phenol has a lower pKa, it is a stronger acid compared to cyclohexanol.
03

Relate pKa to Deprotonation

A compound with a lower pKa (i.e., phenol) is easier to deprotonate because it holds on to its proton less tightly compared to a compound with a higher pKa (i.e., cyclohexanol).
04

Reason for Ease of Deprotonation

Phenol is easier to deprotonate because the phenoxide ion (the conjugate base of phenol) is stabilized by resonance. Cyclohexanol lacks this stabilization, making it harder to deprotonate.

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Key Concepts

These are the key concepts you need to understand to accurately answer the question.

deprotonation
Deprotonation is the process of removing a proton (H+) from a molecule, resulting in the formation of its conjugate base. In the context of acid-base reactions, a compound's pKa value helps us understand how easily it can be deprotonated.

Phenol, with its lower pKa of 10, can be deprotonated more easily than cyclohexanol, which has a higher pKa of 16. The ease of deprotonation is also influenced by the stability of the resulting conjugate base.

Phenol's conjugate base, the phenoxide ion, is stabilized by resonance. This greatly enhances the likelihood of phenol giving up its proton. On the other hand, the conjugate base of cyclohexanol lacks such stabilization, making it harder to deprotonate.
Understanding deprotonation is important for predicting and controlling chemical reactions, especially in organic synthesis and pharmaceutical applications.

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