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Williamson
methyl or primary

Williamson
methyl or primary

Alkoxymercuration
secondary or tertiary

Alkoxymercuration
secondary or tertiary

Alkoxymercuration
secondary or tertiary

Alkoxymercuration
secondary or tertiary

Alkoxymercuration
secondary or tertiary

Alkoxymercuration
secondary or tertiary

Alkoxymercuration
secondary or tertiary

Acid-cleavage

Acid-cleavage

Acid-cleavage

Acid-cleavage

Acid-cleavage

Acid-cleavage
allylic

Acid cleavage
cyclic ether

Acid cleavage
cyclic ether

Epoxidation

Epoxidation

Acid-cat
primary or secondary; SN2-like
tertiary; SN1-like

Acid-cat
primary or secondary; SN2-like
tertiary; SN1-like

Acid-cat
primary or secondary; SN2-like
tertiary; SN1-like

Acid-cat
primary or secondary; SN2-like
tertiary; SN1-like

Base-cat
SN2

Prep of thiols
SN2

Prep of sulfides
Can happen after preparing thiol

Oxidation

Prep of sulfides

Prep of sulfides
Similar to prep of ethers

Prep of sulfides

Epoxy-mercuration

Epoxy-mercuration
