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Chapter 19: Q70 (page 763)

Although p-hydroxybenzoic acid is less acidic than benzoic acid, o-hydroxybenzoic acid is slightly more acidic than benzoic acid. Explain this result.

Short Answer

Expert verified

This occurs due to the stabilization of carbanion.

Step by step solution

01

p-hydroxybenzoic acid

The p-hydroxybenzoic acid is less acidic than benzoic acid. It has an alcohol group at para position to the acidic group of the benzoic acid. Theresonance effect destabilizes the conjugate base.

02

 Step 2: o-hydroxybenzoic acid

The o-hydroxybenzoic acid is more acidic than benzoic acid.It has an alcohol group at ortho position to the acidic group of the benzoic acid.

03

Explanation

The p-hydroxybenzoic acid hasan OH group, whichdonates electron density by its resonance effect, destabilizing the conjugate base and making the acid less acidic than benzoic acid.

Destabilized conjugate base

The o-hydroxybenzoic acid has intramolecular hydrogen bonding, stabilizing the conjugate base and making the compound more acidic than benzoic acid.

Stabilized conjugate base

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Most popular questions from this chapter

Which carboxylic acid has the lower pKa, pyruvic acid (CH3COCOOH)or acetoacetic acid (CH3COCH2COOH) ? Explain your choice.

The pKaof p-methylthiophenol(CH3SC6H4OH) is 9.53. Is p-methylthiophenol more or less reactive in electrophilic aromatic substitution than phenol?

Question: Match each of the following pka values (3.2, 4.9, and 0.2) to the appropriate carboxylic acid:

(a) CH3CH2COOH;[b]CF3COOH;[c]ICH2COOH

Question: Give the IUPAC name for each compound.

a.

b.

c.

d.

Rank the compounds in each group in order of increasing acidity.

a.

b.
See all solutions

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