Aldehydes & Ketones

⚗️ Aldehydes Ketones Reactions

Part 1 of 7 — Carbonyl Chemistry Introduction

1. Carbonyl group (C=O)

polar, electrophilic carbon

2. Aldehydes

RCHO (terminal); Ketones: RCOR (internal)

3. Nucleophilic addition

Nu⁻ attacks electrophilic C

4. Aldehydes more reactive than ketones (less steric hindrance, less electron donation)

Aldehydes more reactive than ketones (less steric hindrance, less electron donation)

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Key Concepts Summary

• Carbonyl group (C=O): polar, electrophilic carbon
• Aldehydes: RCHO (terminal); Ketones: RCOR (internal)
• Nucleophilic addition: Nu⁻ attacks electrophilic C
• Aldehydes more reactive than ketones (less steric hindrance, less electron donation)

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Nucleophilic Addition

Part 2 of 7 — Nucleophilic Addition

1. Nucleophilic addition mechanism

Nu⁻ attacks C=O → alkoxide → protonate

2. Hydride reduction

NaBH₄ (mild) or LiAlH₄ (strong)

3. Cyanide addition

NaCN → cyanohydrin

4. Wittig reaction

Ph₃P=CHR → alkene

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Key Concepts Summary

• Nucleophilic addition mechanism: Nu⁻ attacks C=O → alkoxide → protonate
• Hydride reduction: NaBH₄ (mild) or LiAlH₄ (strong)
• Cyanide addition: NaCN → cyanohydrin
• Wittig reaction: Ph₃P=CHR → alkene

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Grignard & Organolithium Reactions

Part 3 of 7 — Grignard & Organolithium Reactions

1. Grignard reagent (RMgBr) adds to carbonyls

Grignard reagent (RMgBr) adds to carbonyls

2. Formaldehyde + RMgBr → primary alcohol

Formaldehyde + RMgBr → primary alcohol

3. Aldehyde + RMgBr → secondary alcohol

Aldehyde + RMgBr → secondary alcohol

4. Ketone + RMgBr → tertiary alcohol

Ketone + RMgBr → tertiary alcohol

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Key Concepts Summary

• Grignard reagent (RMgBr) adds to carbonyls
• Formaldehyde + RMgBr → primary alcohol
• Aldehyde + RMgBr → secondary alcohol
• Ketone + RMgBr → tertiary alcohol

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Reduction & Oxidation

Part 4 of 7 — Reduction & Oxidation

1. NaBH₄

reduces aldehydes and ketones to alcohols

2. LiAlH₄

reduces all carbonyls including esters and amides

3. Oxidation

Tollens (Ag⁺), Jones, PCC

4. Only aldehydes give positive Tollens test (silver mirror)

Only aldehydes give positive Tollens test (silver mirror)

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Key Concepts Summary

• NaBH₄: reduces aldehydes and ketones to alcohols
• LiAlH₄: reduces all carbonyls including esters and amides
• Oxidation: Tollens (Ag⁺), Jones, PCC
• Only aldehydes give positive Tollens test (silver mirror)

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Acetals & Hemiacetals

Part 5 of 7 — Acetals & Hemiacetals

1. Hemiacetal

one -OH and one -OR on same carbon

2. Acetal

two -OR groups on same carbon (formed in acid, excess alcohol)

3. Acetals are stable under basic conditions → protecting groups

Acetals are stable under basic conditions → protecting groups

4. Cyclic hemiacetals

found in sugars (glucose, fructose)

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Key Concepts Summary

• Hemiacetal: one -OH and one -OR on same carbon
• Acetal: two -OR groups on same carbon (formed in acid, excess alcohol)
• Acetals are stable under basic conditions → protecting groups
• Cyclic hemiacetals: found in sugars (glucose, fructose)

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Problem-Solving Workshop

Part 6 of 7 — Problem-Solving Workshop

1. Predicting nucleophilic addition products

Predicting nucleophilic addition products

2. Designing Grignard-based syntheses

Designing Grignard-based syntheses

3. Choosing appropriate reducing agents

Choosing appropriate reducing agents

4. Using acetals as protecting groups

Using acetals as protecting groups

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Key Concepts Summary

• Predicting nucleophilic addition products
• Designing Grignard-based syntheses
• Choosing appropriate reducing agents
• Using acetals as protecting groups

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Synthesis & Review

Part 7 of 7 — Synthesis & Review

1. Carbonyl chemistry is central to organic synthesis

Carbonyl chemistry is central to organic synthesis

2. Nucleophilic addition is the key reaction

Nucleophilic addition is the key reaction

3. Grignard reactions form C-C bonds

Grignard reactions form C-C bonds

4. Review

carbonyl reactions summary

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Key Concepts Summary

• Carbonyl chemistry is central to organic synthesis
• Nucleophilic addition is the key reaction
• Grignard reactions form C-C bonds
• Review: carbonyl reactions summary

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