Amines & Nitrogen Compounds

⚗️ Amines Nitrogen Compounds

Part 1 of 7 — Amine Classification & Properties

1. Amines

nitrogen with lone pair and up to 3 R groups

2. Primary (RNH₂), secondary (R₂NH), tertiary (R₃N)

Primary (RNH₂), secondary (R₂NH), tertiary (R₃N)

3. Quaternary ammonium (R₄N⁺)

positively charged

4. Amines are bases and nucleophiles

Amines are bases and nucleophiles

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Key Concepts Summary

• Amines: nitrogen with lone pair and up to 3 R groups
• Primary (RNH₂), secondary (R₂NH), tertiary (R₃N)
• Quaternary ammonium (R₄N⁺): positively charged
• Amines are bases and nucleophiles

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Amine Basicity

Part 2 of 7 — Amine Basicity

1. Amine basicity

pKb depends on electron density on nitrogen

2. Alkylamines more basic than aniline (aromatic amine)

Alkylamines more basic than aniline (aromatic amine)

3. Electron-donating groups increase basicity

Electron-donating groups increase basicity

4. Electron-withdrawing groups decrease basicity

Electron-withdrawing groups decrease basicity

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Key Concepts Summary

• Amine basicity: pKb depends on electron density on nitrogen
• Alkylamines more basic than aniline (aromatic amine)
• Electron-donating groups increase basicity
• Electron-withdrawing groups decrease basicity

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Amine Synthesis

Part 3 of 7 — Amine Synthesis

1. Gabriel synthesis

phthalimide + alkyl halide → primary amine

2. Reductive amination

carbonyl + amine + NaBH₃CN → amine

3. Reduction of nitro groups

catalytic hydrogenation or Sn/HCl

4. Hofmann rearrangement

amide → amine with one fewer carbon

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Key Concepts Summary

• Gabriel synthesis: phthalimide + alkyl halide → primary amine
• Reductive amination: carbonyl + amine + NaBH₃CN → amine
• Reduction of nitro groups: catalytic hydrogenation or Sn/HCl
• Hofmann rearrangement: amide → amine with one fewer carbon

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Amine Reactions

Part 4 of 7 — Amine Reactions

1. Alkylation

amines react with alkyl halides (over-alkylation problem)

2. Acylation

amines react with acid chlorides → amides

3. Sulfonamide formation

amines + sulfonyl chlorides

4. Hinsberg test

distinguishes 1°, 2°, 3° amines

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Key Concepts Summary

• Alkylation: amines react with alkyl halides (over-alkylation problem)
• Acylation: amines react with acid chlorides → amides
• Sulfonamide formation: amines + sulfonyl chlorides
• Hinsberg test: distinguishes 1°, 2°, 3° amines

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Diazonium Chemistry

Part 5 of 7 — Diazonium Chemistry

1. Diazotization

primary aromatic amine + HNO₂ → diazonium salt (ArN₂⁺)

2. Sandmeyer reaction

ArN₂⁺ + CuX → ArX (X = Cl, Br, CN)

3. Diazo coupling

ArN₂⁺ + ArOH → azo dye

4. Diazonium salts are versatile synthetic intermediates

Diazonium salts are versatile synthetic intermediates

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Key Concepts Summary

• Diazotization: primary aromatic amine + HNO₂ → diazonium salt (ArN₂⁺)
• Sandmeyer reaction: ArN₂⁺ + CuX → ArX (X = Cl, Br, CN)
• Diazo coupling: ArN₂⁺ + ArOH → azo dye
• Diazonium salts are versatile synthetic intermediates

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Problem-Solving Workshop

Part 6 of 7 — Problem-Solving Workshop

1. Predicting amine basicity from structure

Predicting amine basicity from structure

2. Designing amine synthesis strategies

Designing amine synthesis strategies

3. Drawing diazonium reaction mechanisms

Drawing diazonium reaction mechanisms

4. Comparing amine reactivity patterns

Comparing amine reactivity patterns

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Key Concepts Summary

• Predicting amine basicity from structure
• Designing amine synthesis strategies
• Drawing diazonium reaction mechanisms
• Comparing amine reactivity patterns

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Synthesis & Review

Part 7 of 7 — Synthesis & Review

1. Amines are fundamental in biochemistry (amino acids, neurotransmitters)

Amines are fundamental in biochemistry (amino acids, neurotransmitters)

2. Basicity and nucleophilicity make amines versatile

Basicity and nucleophilicity make amines versatile

3. Diazonium chemistry enables aromatic substitutions

Diazonium chemistry enables aromatic substitutions

4. Review

amine properties and reactions

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Key Concepts Summary

• Amines are fundamental in biochemistry (amino acids, neurotransmitters)
• Basicity and nucleophilicity make amines versatile
• Diazonium chemistry enables aromatic substitutions
• Review: amine properties and reactions

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