Alkene Reactions

⚗️ Alkenes Reactions

Part 1 of 7 — Alkene Structure & Stability

1. Alkenes

C=C double bond (sp² hybridized)

2. Degree of unsaturation

one for each C=C or ring

3. Stability

more substituted = more stable

4. E/Z isomerism

priority-based naming of alkene geometry

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Key Concepts Summary

• Alkenes: C=C double bond (sp² hybridized)
• Degree of unsaturation: one for each C=C or ring
• Stability: more substituted = more stable
• E/Z isomerism: priority-based naming of alkene geometry

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Electrophilic Addition

Part 2 of 7 — Electrophilic Addition

1. Electrophilic addition

π electrons attack electrophile

2. Step 1

electrophile adds to less substituted carbon → carbocation

3. Step 2

nucleophile attacks carbocation

4. Common electrophiles

HX, H₂O/H⁺, X₂

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Key Concepts Summary

• Electrophilic addition: π electrons attack electrophile
• Step 1: electrophile adds to less substituted carbon → carbocation
• Step 2: nucleophile attacks carbocation
• Common electrophiles: HX, H₂O/H⁺, X₂

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Markovnikov & Anti-Markovnikov

Part 3 of 7 — Markovnikov & Anti-Markovnikov

1. Markovnikov's rule

H adds to carbon with more H's

2. Carbocation stability determines regiochemistry

Carbocation stability determines regiochemistry

3. Anti-Markovnikov

HBr/peroxides (radical addition)

4. Peroxides reverse the selectivity via radical mechanism

Peroxides reverse the selectivity via radical mechanism

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Key Concepts Summary

• Markovnikov's rule: H adds to carbon with more H's
• Carbocation stability determines regiochemistry
• Anti-Markovnikov: HBr/peroxides (radical addition)
• Peroxides reverse the selectivity via radical mechanism

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Hydroboration-Oxidation

Part 4 of 7 — Hydroboration-Oxidation

1. Hydroboration-oxidation

anti-Markovnikov, syn addition

2. BH₃ adds B to less substituted carbon

BH₃ adds B to less substituted carbon

3. Oxidation with H₂O₂/NaOH gives anti-Markovnikov alcohol

Oxidation with H₂O₂/NaOH gives anti-Markovnikov alcohol

4. Syn addition

H and OH add to same face

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Key Concepts Summary

• Hydroboration-oxidation: anti-Markovnikov, syn addition
• BH₃ adds B to less substituted carbon
• Oxidation with H₂O₂/NaOH gives anti-Markovnikov alcohol
• Syn addition: H and OH add to same face

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Oxidation & Reduction

Part 5 of 7 — Oxidation & Reduction

1. Catalytic hydrogenation

H₂/Pd → alkane (syn addition)

2. Ozonolysis

O₃ then Zn/H₂O cleaves C=C → carbonyl compounds

3. Dihydroxylation

OsO₄ → cis-diol (syn addition)

4. Epoxidation

mCPBA → epoxide

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Key Concepts Summary

• Catalytic hydrogenation: H₂/Pd → alkane (syn addition)
• Ozonolysis: O₃ then Zn/H₂O cleaves C=C → carbonyl compounds
• Dihydroxylation: OsO₄ → cis-diol (syn addition)
• Epoxidation: mCPBA → epoxide

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Problem-Solving Workshop

Part 6 of 7 — Problem-Solving Workshop

1. Predicting addition products and regiochemistry

Predicting addition products and regiochemistry

2. Drawing mechanisms for electrophilic addition

Drawing mechanisms for electrophilic addition

3. Comparing Markovnikov vs anti-Markovnikov outcomes

Comparing Markovnikov vs anti-Markovnikov outcomes

4. Designing multi-step syntheses with alkenes

Designing multi-step syntheses with alkenes

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Key Concepts Summary

• Predicting addition products and regiochemistry
• Drawing mechanisms for electrophilic addition
• Comparing Markovnikov vs anti-Markovnikov outcomes
• Designing multi-step syntheses with alkenes

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Synthesis & Review

Part 7 of 7 — Synthesis & Review

1. Alkenes are versatile synthetic intermediates

Alkenes are versatile synthetic intermediates

2. Regiochemistry and stereochemistry are key considerations

Regiochemistry and stereochemistry are key considerations

3. Multiple reagents give different products from same alkene

Multiple reagents give different products from same alkene

4. Review

alkene reaction summary table

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Key Concepts Summary

• Alkenes are versatile synthetic intermediates
• Regiochemistry and stereochemistry are key considerations
• Multiple reagents give different products from same alkene
• Review: alkene reaction summary table

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