Ethers Flashcards
1
Q
Ether Cleavage
A
Reactant: Ether
Reagent: HBr or HI and heat
Product: Alcohol and an Alkyl Halide
Mechanism: SN1 for a tertiary, benzyllic, or allylic carbocation
Mechanism: SN2 for a vinyllic, arllyic, methyl, or primary carbocation
The nucleophile will attack the side that will form the most stable carbocation. If both sides form the same carbocation, then it will attack the side that is least sterically hindered. If it is a vinyl or aryl group the oxygen will ALWAYS remain with the vinyl or aryl group.
