Exam (elaborations)
Chemical Reactions of Carboxylic Acids
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Chemical Reactions of Carboxylic AcidsT5
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Chemical Reactions of Carboxylic Acids✅
Acidity- Like alcohols, carboxylic acids evolve hydrogen gas when
reacting with metal and form salts with alkalis. Unlike phenols, they require
weaker base like sodium carbonate to evolve carbon dioxide
Smaller pKa value, stronger the acid
Trifluroacetic acid is the strongest organic acid (pKa = 0.23)
Carboxylic acids tend to be weaker than mineral acids but stronger than
alcohols and phenols
Acidic nature of carboxyl group is due to the breaking of O-H bond, due to
positively charged O weakening the bond as well as resonance stabilization
of carboxylate ion
✅
Effect of Substituents on Acidity of Carboxylic Acid- Electron withdrawing
groups increase stability by dispersing negative charge via resonance
effect
Electron donating groups decrease stability by intensifying negative charge
Directly substituted phenyl and vinyl actually increase stability despite
decrease in resonance effect
Order of acidity for hybridization
sp3 > sp2 > sp
Order of increasing acidity
Ph < I < Br < Cl < F < CN < NO2 < CF3
✅
Esterification- Carboxylic acids react with alcohol/phenol in the presence
of mineral acids like conc. H2SO4 and HCl as a gas (as catalyst) to
produce esters
Mechanism
Protonation of carbonyl oxygen
Nucleophilic addition of alcohol
Loss of water molecule and proton
✅
Anhydride Formation- Carboxylic acids heat with mineral acids like conc.
H2SO4 or P2O5 to give us anhydrides
Acid anhydrides are formed by the elimination of a water molecule
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