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Carboxylic Acids & Derivatives
Carboxylic acids and their derivatives share one carbonyl-based reactivity pattern. You will learn what controls acidity, rank the derivatives by reactivity, and follow nucleophilic acyl substitution through esterification, hydrolysis, amide chemistry, and reductions.
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What this chapter covers
- Carboxylic Acids: Structure & Acidity. The carboxylate ion is resonance-stabilized, and substituents tune how strong the acid is. Both ideas are exam favorites.
- Reactivity & Nucleophilic Acyl Substitution. Every acid derivative reacts by the same addition-elimination pattern, and the reactivity order tells you which conversions are allowed.
- Esters: Fischer Esterification & Saponification. Esters are made by an equilibrium and destroyed either reversibly by acid or irreversibly by base. Know which is which.
- Amides, Anhydrides & Reductions. Amides are the toughest derivatives to break, and metal hydrides split the derivatives into predictable alcohols and amines.
Key points to know
- Carboxylates are resonance stabilized, so acids have pKa about 4 to 5
- Electron-withdrawing groups (halogens, NO₂) increase acidity; the effect drops with distance
- Mechanism: nucleophile adds, tetrahedral intermediate, leaving group leaves
- Reactivity: acid chloride > anhydride > ester ≈ acid > amide
- Fischer: RCOOH + R′OH, H⁺ catalyst, reversible; drive with excess alcohol or water removal
- Saponification is irreversible because the carboxylate is formed
- Amide N lone pair delocalizes: planar, non-basic, hard to hydrolyze
- LiAlH₄: acid or ester to primary alcohol, amide to amine
Try a practice question
Which is the strongest acid?
- mol:CC(=O)O{acetic acid}
- mol:ClCC(=O)O{chloroacetic acid}
- mol:ClC(Cl)(Cl)C(=O)O{trichloroacetic acid}
- mol:CCC(=O)O{propanoic acid}
Show the answer
C. Three chlorines withdraw electron density the most and best stabilize the carboxylate. Propanoic acid has an extra donating alkyl group and is slightly weaker than acetic acid.
Common questions
What does this chapter cover?
Carboxylic Acids & Derivatives covers Carboxylic Acids: Structure & Acidity, Reactivity & Nucleophilic Acyl Substitution, Esters: Fischer Esterification & Saponification, Amides, Anhydrides & Reductions.
What should I know first?
Carboxylates are resonance stabilized, so acids have pKa about 4 to 5 Electron-withdrawing groups (halogens, NO₂) increase acidity; the effect drops with distance Mechanism: nucleophile adds, tetrahedral intermediate, leaving group leaves
22 original practice questions accompany this chapter in the app. Spaced review brings missed ideas back at the right time; it helps memory but cannot promise you will not miss an idea again.