Alcohols & Ethers

⚗️ Alcohols Ethers

Part 1 of 7 — Alcohol Nomenclature & Properties

1. Alcohols

R-OH; named with -ol suffix

2. Classification

primary (1°), secondary (2°), tertiary (3°)

3. Hydrogen bonding → higher boiling points than alkanes

Hydrogen bonding → higher boiling points than alkanes

4. Acidity

pKa ~16-18 (weaker than water, stronger than alkanes)

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Key Concepts Summary

• Alcohols: R-OH; named with -ol suffix
• Classification: primary (1°), secondary (2°), tertiary (3°)
• Hydrogen bonding → higher boiling points than alkanes
• Acidity: pKa ~16-18 (weaker than water, stronger than alkanes)

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Alcohol Synthesis

Part 2 of 7 — Alcohol Synthesis

1. Grignard reaction

RMgBr + carbonyl → alcohol

2. Hydration of alkenes

Markovnikov (H₃O⁺) or anti-Markovnikov (BH₃)

3. Reduction of carbonyls

NaBH₄ or LiAlH₄

4. Hydrolysis of esters gives alcohols

Hydrolysis of esters gives alcohols

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Key Concepts Summary

• Grignard reaction: RMgBr + carbonyl → alcohol
• Hydration of alkenes: Markovnikov (H₃O⁺) or anti-Markovnikov (BH₃)
• Reduction of carbonyls: NaBH₄ or LiAlH₄
• Hydrolysis of esters gives alcohols

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Alcohol Reactions

Part 3 of 7 — Alcohol Reactions

1. Dehydration

H₂SO₄/heat → alkene (E1 for 3°, E2 for 1°)

2. Oxidation

PCC (1° → aldehyde), Jones/CrO₃ (1° → carboxylic acid, 2° → ketone)

3. Conversion to alkyl halides

HX, PBr₃, SOCl₂

4. 3° alcohols cannot be oxidized

3° alcohols cannot be oxidized

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Key Concepts Summary

• Dehydration: H₂SO₄/heat → alkene (E1 for 3°, E2 for 1°)
• Oxidation: PCC (1° → aldehyde), Jones/CrO₃ (1° → carboxylic acid, 2° → ketone)
• Conversion to alkyl halides: HX, PBr₃, SOCl₂
• 3° alcohols cannot be oxidized

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Ether Nomenclature & Synthesis

Part 4 of 7 — Ether Nomenclature & Synthesis

1. Ethers

R-O-R; named as alkoxy + alkane

2. Williamson ether synthesis

alkoxide + primary alkyl halide (SN2)

3. Ethers are relatively unreactive (good solvents)

Ethers are relatively unreactive (good solvents)

4. Crown ethers

cyclic ethers that complex cations

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Key Concepts Summary

• Ethers: R-O-R; named as alkoxy + alkane
• Williamson ether synthesis: alkoxide + primary alkyl halide (SN2)
• Ethers are relatively unreactive (good solvents)
• Crown ethers: cyclic ethers that complex cations

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Ether Reactions

Part 5 of 7 — Ether Reactions

1. Acid-catalyzed cleavage

HI or HBr cleaves ethers

2. Epoxides

strained three-membered ring ethers

3. Epoxide ring-opening

nucleophilic attack at less substituted carbon (base) or more substituted (acid)

4. Epoxides are much more reactive than simple ethers

Epoxides are much more reactive than simple ethers

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Key Concepts Summary

• Acid-catalyzed cleavage: HI or HBr cleaves ethers
• Epoxides: strained three-membered ring ethers
• Epoxide ring-opening: nucleophilic attack at less substituted carbon (base) or more substituted (acid)
• Epoxides are much more reactive than simple ethers

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Problem-Solving Workshop

Part 6 of 7 — Problem-Solving Workshop

1. Predicting alcohol oxidation products

Predicting alcohol oxidation products

2. Designing Grignard synthesis strategies

Designing Grignard synthesis strategies

3. Comparing alcohol reaction pathways

Comparing alcohol reaction pathways

4. Analyzing epoxide ring-opening regiochemistry

Analyzing epoxide ring-opening regiochemistry

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Key Concepts Summary

• Predicting alcohol oxidation products
• Designing Grignard synthesis strategies
• Comparing alcohol reaction pathways
• Analyzing epoxide ring-opening regiochemistry

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Synthesis & Review

Part 7 of 7 — Synthesis & Review

1. Alcohols are versatile functional groups

Alcohols are versatile functional groups

2. Oxidation state changes determine product

Oxidation state changes determine product

3. Ethers as solvents and protecting groups

Ethers as solvents and protecting groups

4. Review

alcohol and ether transformations

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Key Concepts Summary

• Alcohols are versatile functional groups
• Oxidation state changes determine product
• Ethers as solvents and protecting groups
• Review: alcohol and ether transformations

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