Question

Consider the following compounds: CONCOc1ccccc1 Experimentally, phenol is found to be a stronger acid than methanol. Explain this difference in terms of the structures of the conjugate bases. (Hint: A more stable conjugate base favors ionization. Only one of the conjugate bases can be stabilized by resonance.)

Short answer

Phenol is stronger due to the resonance-stabilized phenoxide ion.

Step-by-step solution

Identify the compounds

The given compounds are phenol and methanol. Their chemical formulas are C₆H₅OH for phenol and CH₃OH for methanol.

Understand the acid-base reaction

When phenol or methanol donates a proton (H⁺), they form their respective conjugate bases, namely phenoxide ion (C₆H₅O⁻) and methoxide ion (CH₃O⁻). The stability of these conjugate bases determines the acidity of the original compounds.

Analyze the resonance stability of phenoxide

In phenol, the conjugate base is the phenoxide ion. It can undergo resonance because the negative charge on the oxygen is delocalized onto the aromatic ring. This delocalization leads to several resonance structures, making the phenoxide ion more stable.

Analyze the methoxide ion structure

Methanol, when it loses a proton, forms methoxide ion. This ion does not have any resonance structures since the negative charge is localized on the oxygen atom, making it less stable compared to the phenoxide ion.

Compare conjugate base stability

The resonance stabilization in the phenoxide ion makes it more stable than the methoxide ion, which lacks resonance. The greater stability of the phenoxide ion means that phenol is a stronger acid than methanol, as a more stable conjugate base promotes ionization.

Key concepts

Phenol

Phenol is an aromatic compound consisting of a hydroxyl group (-OH) attached to a benzene ring. This structure is important in acid-base chemistry because phenol can donate a proton (H⁺) from its hydroxyl group, forming the phenoxide ion

• Chemical Formula: C₆H₅OH
• Structure: Hydroxyl group (-OH) attached to an aromatic ring

Being an acidic compound, phenol is unique compared to aliphatic alcohols like methanol. It has greater acidity, signifying enhanced ability to ionize and release a proton. This difference is crucial when comparing phenol to compounds like methanol, where the arylic nature of phenol plays a key role in its chemical behavior, particularly in the enhancement of acidity through stabilization of its conjugate base.

Conjugate Base Stability

The stability of a conjugate base directly influences the acidity of a compound. More stable conjugate bases result in stronger acids as they favor dissociation. In the case of phenol and methanol:

• Phenol forms the phenoxide ion (C₆H₅O⁻) upon losing a proton.
• Methanol forms the methoxide ion (CH₃O⁻) when it loses a proton.

The phenoxide ion is more stable due to resonance, a key factor in determining the conjugate base stability. This increased stability in the case of phenol's conjugate base leads to phenol being a stronger acid than methanol. The inability of the methoxide ion to undergo resonance results in higher localization of charge, leading to reduced stability and lower acidity of methanol compared to phenol. Stability is crucial as it allows the conjugate base to be less reactive and helps maintain equilibrium towards ionization.

Resonance Structures

Resonance structures are critical for understanding the stability of the phenoxide ion formed from phenol. They demonstrate how the negative charge can be delocalized over a molecular structure, which in turn stabilizes the ion. In the phenoxide ion:

• The lone pair of electrons from the oxygen can be delocalized into the benzene ring.
• This delocalization results in multiple resonance structures.

Since resonance allows charge distribution across several atoms, it reduces the energy and, hence, increases the stability of the ion. Resonance is absent in the methoxide ion; hence, it remains less stable with the negative charge stuck on the oxygen atom. This difference in resonance abilities directly translates to the difference in acid strength between phenol and methanol. The resonance capable phenoxide ion stabilizes the conjugate base, whereas the methoxide ion, devoid of such stabilization, does not, leading to significant differences in their acidic properties.