Carboxylic Acid Derivatives

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Last updated 10:21 PM on 7/17/26
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12 Terms

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Acid chloride

Carboxylic acid + SOCl2

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Ester (Fischer esterification)

Carboxylic acid + R’OH + HCl

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Amide

Carboxylic acid + amine + DCC

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Carboxylic acid (AC derived)

Acid chloride + NaOH + H2O (NaCl byproduct)

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Ester (AC derived)

Acid chloride + R’OH + pyridine

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Amide (AC derived)

Acid chloride + amine (2 eq.)

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Carboxylic acid (AA derived)

Acid anhydride + NaOH + H2O (sodium carboxylate byproduct)

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Ester (AA derived)

Acid anhydride + R’OH + pyridine

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Amide (AA derived)

Acid anhydride + amine (2 eq.)

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Ester hydrolysis under ACIDIC conditions

Raises ground state E of electrophile (makes it more electrophilic, such as protonation step)

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Ester hydrolysis under BASIC conditions

Raises ground state E of nucleophile (makes it more nucleophilic, such as resonance creating negative formal charge)

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Equilibrium of ester hydrolysis under basic conditions

Ester and NaOH favors formation of carboxylate, so H3O+ workup must be implemented to shift equilibrium