Organic Chemistry Practice Problems and Problem Sets
ether hydrolysis
Write out a mechanism for the reaction below using curved arrows. Be sure to include formal charges.
Ethers react with 2 equivalents of H-X to form water and two equivalents of alkyl halide.
In this case, the ether was cyclic, so the ring had to open up.
The reaction can go through either an SN1 or SN2 mechanism. Since this was a primary ether, it will go through an SN2 mechanism (the carbocation is too unstable for the reaction to go SN1).
MendelSet practice problem # 700 submitted by Matt on July 21, 2011.