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Protecting Groups: How They Work

Protecting Groups: How They Work. Protecting Groups: Alcohol Alkylation. Alcohol Groups do not “Survive” Many Organic Reactions Alkylation (Ether Formation) Protects OH’s During Synthesis Can Remove the Protecting Group w/ Dilute Aqueous Acid

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Protecting Groups: How They Work

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  1. Protecting Groups: How They Work

  2. Protecting Groups: Alcohol Alkylation • Alcohol Groups do not “Survive” Many Organic Reactions • Alkylation (Ether Formation) Protects OH’s During Synthesis • Can Remove the Protecting Group w/ Dilute Aqueous Acid • Generally Dissolve Alcohol in Acid, THEN add Isobutylene • Addition in this Manner Minimizes Isobutylene Dimerization • Let’s See Why We Might Want to Use a Protecting Group

  3. Protecting Groups: Silyl Ethers • Silyl Ethers Stable Over a 4-12 pH Range (Acidic and Basic) • Can Survive Conditions of Many Organic Reactions • Typically Removed w/ Flouride Source (NBu4F; aka TBAF) • Silyl Ethers More Volatile Than Alcohols (GC Applications)

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