OrgoChem II

Alcohols

Oxidation substitution protection and synthesis roles

Summary

Alcohols are multipurpose. Learn oxidation levels and common transformations. Full reference is on the external link.

What you need to know:

This topic covers alcohols. Focus on mastering the key concepts in the "Must know checklist" below. Follow the study steps systematically, and use practice problems to reinforce your understanding. The external reference provides comprehensive coverage of all concepts.

Video Tutorial

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Oxidation of Alcohols

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Must know checklist

0 / 5 complete

Oxidation levels1° alcohol → aldehyde → carboxylic acid; 2° alcohol → ketone; 3° alcohol doesn't oxidize; know which reagents stop where
Oxidation of Alcohols - Primary, Secondary, Tertiary→
Oxidation reagentsPCC/DMP (stops at aldehyde), Jones/CrO3 (goes to acid), Swern (aldehyde), KMnO4/Na2Cr2O7 (acid); MnO2 (selective for allylic alcohols)
Oxidation Reagents - PCC, Jones, Swern, DMP→
Alcohol to leaving groupTsCl/pyridine → tosylate; MsCl/pyridine → mesylate; both are excellent leaving groups for SN2/E2
Converting Alcohols to Leaving Groups - Tosylates and Mesylates→
Protecting groupsTBDMS/TIPS silyl ethers protect OH from oxidation/reduction; remove with F- or acid; essential in multi-step synthesis
Protecting Groups for Alcohols - Silyl Ethers→
Dehydrationacid-catalyzed (H2SO4/heat) gives E1 mechanism with carbocation rearrangements; Zaitsev product; can form ethers at lower temp
Acid-Catalyzed Dehydration of Alcohols→

Common mistakes

Using PCC when you need carboxylic acid (PCC stops at aldehyde)

Forgetting that 3° alcohols don't oxidize

Not converting OH to tosylate before SN2 when needed