Question

Orgo II Tutorial: Ether Synthesis

Answer 1

\({\bf{Dehydration~Synthesis:}}\) NOTE: this is not often used because this mechanism usually leads to alkenes not ethers

Overview:
ROH + HOR --> ROR
using acid HA (will use sulfuric acid as a demonstration)

Mechanism:

Answer 2

then a water molecule attacks the hydrogen on that central oxygen, completing the ether synthesis

Answer 3

\({\bf{Williamson~Ether~Synthesis:}}\)

Overview:
R-O-Na + R-LG --> ROR + NaLG using SN2 mechanism where the O in the alkoxide attacks the R group on the LG

where LG is a leaving group like Br, I, or OSO2R" (see tosylates, mesylates, triflates)

Answer 4

note: phenols, which are more acidic, can use NaOH instead of NaH as the base

Answer 5

\({\bf{Alkoxymercuration-Demercuration:}}\) almost the same as oxymercuration-demurcuration except we will use the reagent

Hg(O2CCF3)2 + t-BuOH to add a Hg(O2CCF3) instead of an Hg(OAc) and t-BuOH instead of an OH

Answer 6

Anyway, that's the end of my tutorial, I hope it was a helpful resource. Source material is Organic Chemistry 12th edition by Solomons, et. al.