Question

What products are obtained when ethyl isopropylether is cleaved with hot HI?

• A. Ethanol and 2-iodo-2-methylpropane
• B. Ethanol and 2-methylpropane
• C. Iodoethane and Isopropyl alcohol
• D. Iodoethane and 2-methylpropane

Answer 1

The correct option is C Iodoethane and Isopropyl alcohol

Ethers can be reactive under ​drastic reaction conditions (high temperature, high concentration) due to the cleavage of the C-O bond.​
In first step of the reaction, protonation of ether $\left(O\right)$ group take place.
In second step, $I^{-}$ will undergo $S_{N}2$ nucleophilic attack.
The reaction of ethyl isopropylether is with concentrated HI give Iodoethane and Isopropyl alcohol. Hence option (c) is correct. The reaction is as follow: