Carboxylic Acids & Derivatives

⚗️ Carboxylic Acids Derivatives

Part 1 of 7 — Carboxylic Acid Properties

1. Carboxylic acids

RCOOH (pKa ~4-5)

2. Acidity due to resonance stabilization of carboxylate anion

Acidity due to resonance stabilization of carboxylate anion

3. Hydrogen bonding → high boiling points, dimer formation

Hydrogen bonding → high boiling points, dimer formation

4. Inductive effects of substituents affect acidity

Inductive effects of substituents affect acidity

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Key Concepts Summary

• Carboxylic acids: RCOOH (pKa ~4-5)
• Acidity due to resonance stabilization of carboxylate anion
• Hydrogen bonding → high boiling points, dimer formation
• Inductive effects of substituents affect acidity

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Nucleophilic Acyl Substitution

Part 2 of 7 — Nucleophilic Acyl Substitution

1. Nucleophilic acyl substitution

Nu attacks C=O → tetrahedral intermediate → leaving group departs

2. Different from nucleophilic addition (no leaving group expulsion with aldehydes/ketones)

Different from nucleophilic addition (no leaving group expulsion with aldehydes/ketones)

3. Reactivity order

acid chloride > anhydride > ester > amide

4. Better leaving group = more reactive

Better leaving group = more reactive

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Key Concepts Summary

• Nucleophilic acyl substitution: Nu attacks C=O → tetrahedral intermediate → leaving group departs
• Different from nucleophilic addition (no leaving group expulsion with aldehydes/ketones)
• Reactivity order: acid chloride > anhydride > ester > amide
• Better leaving group = more reactive

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Acid Chlorides & Anhydrides

Part 3 of 7 — Acid Chlorides & Anhydrides

1. Acid chloride (RCOCl)

most reactive acyl derivative

2. Made from RCOOH + SOCl₂ or (COCl)₂

Made from RCOOH + SOCl₂ or (COCl)₂

3. Anhydride (RCO-O-COR)

moderately reactive

4. Both react with alcohols → esters, amines → amides

Both react with alcohols → esters, amines → amides

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Key Concepts Summary

• Acid chloride (RCOCl): most reactive acyl derivative
• Made from RCOOH + SOCl₂ or (COCl)₂
• Anhydride (RCO-O-COR): moderately reactive
• Both react with alcohols → esters, amines → amides

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Esters & Amides

Part 4 of 7 — Esters & Amides

1. Esters (RCOOR')

moderate reactivity

2. Fischer esterification

RCOOH + R'OH ⇌ RCOOR' + H₂O (acid catalyzed)

3. Amides (RCONHR')

least reactive (nitrogen lone pair resonance)

4. Saponification

ester + NaOH → carboxylate + alcohol

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Key Concepts Summary

• Esters (RCOOR'): moderate reactivity
• Fischer esterification: RCOOH + R'OH ⇌ RCOOR' + H₂O (acid catalyzed)
• Amides (RCONHR'): least reactive (nitrogen lone pair resonance)
• Saponification: ester + NaOH → carboxylate + alcohol

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Interconversion of Derivatives

Part 5 of 7 — Interconversion of Derivatives

1. Can go "downhill" in reactivity

acid chloride → anhydride → ester → amide

2. Cannot easily go "uphill" without special reagents

Cannot easily go "uphill" without special reagents

3. Reduction

LiAlH₄ reduces esters → 2 alcohols, amides → amines

4. Hydrolysis

each derivative → carboxylic acid + nucleophile

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Key Concepts Summary

• Can go "downhill" in reactivity: acid chloride → anhydride → ester → amide
• Cannot easily go "uphill" without special reagents
• Reduction: LiAlH₄ reduces esters → 2 alcohols, amides → amines
• Hydrolysis: each derivative → carboxylic acid + nucleophile

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Problem-Solving Workshop

Part 6 of 7 — Problem-Solving Workshop

1. Predicting products of acyl substitution

Predicting products of acyl substitution

2. Ranking derivative reactivity

Ranking derivative reactivity

3. Designing synthesis routes through acid derivatives

Designing synthesis routes through acid derivatives

4. Analyzing reaction conditions and mechanisms

Analyzing reaction conditions and mechanisms

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Key Concepts Summary

• Predicting products of acyl substitution
• Ranking derivative reactivity
• Designing synthesis routes through acid derivatives
• Analyzing reaction conditions and mechanisms

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Synthesis & Review

Part 7 of 7 — Synthesis & Review

1. Carboxylic acid derivatives are interconnected

Carboxylic acid derivatives are interconnected

2. Reactivity reflects leaving group ability

Reactivity reflects leaving group ability

3. These reactions are essential in biochemistry (proteins, fats)

These reactions are essential in biochemistry (proteins, fats)

4. Review

acyl substitution reactions

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Key Concepts Summary

• Carboxylic acid derivatives are interconnected
• Reactivity reflects leaving group ability
• These reactions are essential in biochemistry (proteins, fats)
• Review: acyl substitution reactions

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