Question

Treatment of an alkyl halide with AgNO₃ in alcohol often promotes ionization.

Ag⁺ + R-Cl → AgCl + R⁺

When 4-chloro-2-methylhex-2-ene reacts with AgNO₃ in ethanol, two isomeric ethers are formed. Suggest structures, and propose a mechanism for their formation.

Short answer

The two isomeric ethers formed are shown as,

Step-by-step solution

Ionization

Ionization is forming electrically charged atoms from neutral atoms and having a greater tendency to form ionic bonds.If an atom losses electrons, it becomes a positively charged atom.

Mechanism for the formation of two isomeric ethers

When 4-chloro-2-methylhex-2-ene reacts with AgNO₃ in ethanol, the two allylic tautomers are formed. Further reaction with ethanol gives two isomeric ethers with the same chemical formula, but the ether group is attached at different positions from one another. The mechanism for the formation of two isomeric ethers is shown below as,

A mechanism for the formation of two isomeric ethers