Exactly of a symmetrical dialkyl ether () is subjected to cleavage by being heated strongly with a v — Alcohols Phenols and Ethers Chemistry Question
Question
Exactly $1 \text{ mole}$ of a symmetrical dialkyl ether ($R-O-R$) is subjected to cleavage by being heated strongly with a vast excess of concentrated hydroiodic acid ($HI$). Assuming the reaction goes to absolute completion, what is the total number of moles of alkyl iodide ($R-I$) isolated?
Answer: 2
💡 Solution & Explanation
With cold/dilute HI, 1 mole of ether yields 1 mole of alcohol and 1 mole of alkyl iodide. However, with an *excess* of strong, hot HI, the initially formed alcohol molecule is further substituted by a second molecule of HI to form a second molecule of alkyl iodide. The net reaction is $R-O-R + 2HI \xrightarrow{\Delta} 2 R-I + H_2O$. Thus, 2 moles are produced.
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