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

A student heats 5.41 g of anisole with excess concentrated hydrogen iodide…

Try it on paper first. A hint, the key idea and the worked solution are here when you need them.

A student heats $5.41\ \text{g}$ of anisole with excess concentrated hydrogen iodide. The yield of each product is $90\ \%$ . Use $108.14\ \text{g/mol}$ for anisole, $94.113\ \text{g/mol}$ for phenol and $141.939\ \text{g/mol}$ for iodomethane. Find the mass of phenol and the mass of iodomethane. Then say what a further molecule of HI does to the phenol.

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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