Williamson ether synthesis
Alcohols, Phenols and Ethers · Chemistry
Study notes
Synthesize CH₃OCH₂CH₃ (ethyl methyl ether) by Williamson. Step 1: Two combos: CH₃ONa + CH₃CH₂Br, or CH₃CH₂ONa + CH₃Br. Step 2: Both use 1° halides → SN2 clean, no elimination. Step 3: Pick either: CH₃ONa + BrCH₂CH₃ → CH₃OCH₂CH₃. Step 4: For tert-butyl methyl ether: (CH₃)₃CONa + CH₃I (NOT (CH₃)₃CBr + CH₃ONa — elimination!). Choose the less hindered halide!