HardChemistryHigh School (11–12)Organic Compounds with Functional Groups › Alcohols, Phenols and EthersNumerical

The three ethers of formula C₄H₁₀O are methoxypropane, ethoxyethane and 2-methoxypropane…

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The three ethers of formula $\text{C}_{4}\text{H}_{10}\text{O}$ are methoxypropane, ethoxyethane and 2-methoxypropane. Each is heated separately with an excess of hydrogen iodide until no alcohol is left. Find the total number of different alkyl iodides obtained from the three, counting each iodide once. Then find how many moles of HI one mole of ethoxyethane uses, and how many moles of HI one mole of 2-methoxypropane uses.

Need a reminder? The key ideaShow

HI cleaves the C-O bond. Iodide attacks the less crowded carbon (or the tertiary one). An aryl C-O bond stays, so an aryl alkyl ether gives a phenol and an alkyl iodide. Excess HI turns an alkyl ether into two alkyl iodides. The net dipole of two bond dipoles $\mu$ at angle $\theta$ is $2\mu\cos(\theta/2)$ .

The worked solution

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Work it out on paper first. It is fine to get stuck or make a mistake: that is how we learn. When you are ready, go through the solution one step at a time, and check each step against your own.

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