Acids & Bases in Organic Chemistry

⚗️ Acids Bases Organic

Part 1 of 7 — Brønsted-Lowry Acids & Bases

1. Brønsted acid

proton (H⁺) donor

2. Brønsted base

proton acceptor

3. Conjugate acid-base pairs differ by one proton

Conjugate acid-base pairs differ by one proton

4. Stronger acid → weaker conjugate base

Stronger acid → weaker conjugate base

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Key Concepts Summary

• Brønsted acid: proton (H⁺) donor
• Brønsted base: proton acceptor
• Conjugate acid-base pairs differ by one proton
• Stronger acid → weaker conjugate base

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pKa & Acid Strength

Part 2 of 7 — pKa & Acid Strength

1. Ka = [H⁺][A⁻]/[HA]; pKa = -log(Ka)

Ka = [H⁺][A⁻]/[HA]; pKa = -log(Ka)

2. Lower pKa = stronger acid

Lower pKa = stronger acid

3. pKa scale

HI (~-10) to CH₄ (~50)

4. Equilibrium favors the weaker acid/base side

Equilibrium favors the weaker acid/base side

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Key Concepts Summary

• Ka = [H⁺][A⁻]/[HA]; pKa = -log(Ka)
• Lower pKa = stronger acid
• pKa scale: HI (~-10) to CH₄ (~50)
• Equilibrium favors the weaker acid/base side

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Factors Affecting Acidity

Part 3 of 7 — Factors Affecting Acidity

1. Electronegativity

more EN atom stabilizes negative charge → stronger acid

2. Atom size

larger atoms stabilize charge → stronger acid (HI > HF)

3. Resonance

delocalization stabilizes conjugate base → stronger acid

4. Inductive effects

electron-withdrawing groups increase acidity

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Key Concepts Summary

• Electronegativity: more EN atom stabilizes negative charge → stronger acid
• Atom size: larger atoms stabilize charge → stronger acid (HI > HF)
• Resonance: delocalization stabilizes conjugate base → stronger acid
• Inductive effects: electron-withdrawing groups increase acidity

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Lewis Acids & Bases

Part 4 of 7 — Lewis Acids & Bases

1. Lewis acid

electron pair acceptor

2. Lewis base

electron pair donor

3. BF₃ is a Lewis acid (empty p orbital)

BF₃ is a Lewis acid (empty p orbital)

4. Nucleophiles are Lewis bases; electrophiles are Lewis acids

Nucleophiles are Lewis bases; electrophiles are Lewis acids

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Key Concepts Summary

• Lewis acid: electron pair acceptor
• Lewis base: electron pair donor
• BF₃ is a Lewis acid (empty p orbital)
• Nucleophiles are Lewis bases; electrophiles are Lewis acids

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Predicting Acid-Base Reactions

Part 5 of 7 — Predicting Acid-Base Reactions

1. Equilibrium favors formation of weaker acid + weaker base

Equilibrium favors formation of weaker acid + weaker base

2. Compare pKa values to predict direction

Compare pKa values to predict direction

3. Strong acid + strong base → complete reaction

Strong acid + strong base → complete reaction

4. Curved arrow notation shows electron flow

Curved arrow notation shows electron flow

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Key Concepts Summary

• Equilibrium favors formation of weaker acid + weaker base
• Compare pKa values to predict direction
• Strong acid + strong base → complete reaction
• Curved arrow notation shows electron flow

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Problem-Solving Workshop

Part 6 of 7 — Problem-Solving Workshop

1. Ranking acids by pKa

Ranking acids by pKa

2. Predicting products of acid-base reactions

Predicting products of acid-base reactions

3. Drawing curved arrow mechanisms

Drawing curved arrow mechanisms

4. Analyzing effects of substituents on acidity

Analyzing effects of substituents on acidity

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Key Concepts Summary

• Ranking acids by pKa
• Predicting products of acid-base reactions
• Drawing curved arrow mechanisms
• Analyzing effects of substituents on acidity

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Synthesis & Review

Part 7 of 7 — Synthesis & Review

1. Acid-base chemistry is foundational for mechanisms

Acid-base chemistry is foundational for mechanisms

2. pKa determines proton transfer direction

pKa determines proton transfer direction

3. Lewis acid/base concept is broader and essential

Lewis acid/base concept is broader and essential

4. Review

acidity trends and predictions

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Key Concepts Summary

• Acid-base chemistry is foundational for mechanisms
• pKa determines proton transfer direction
• Lewis acid/base concept is broader and essential
• Review: acidity trends and predictions

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