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

Each C-O bond in an ether has a bond dipole of about 1.2 D…

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

Each C-O bond in an ether has a bond dipole of about $1.2\ \text{D}$ . The two bonds meet at the oxygen atom at an angle of $111.7^\circ$ in methoxymethane. Find the net dipole of the two bonds. Then find the net dipole if the angle were $104.5^\circ$ , as in water. Then say what the answer for a straight (180 $^\circ$ ) arrangement would be.

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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← A student heats 25.0 g of ethanol with concentrated sulphuric acid at 413 K and distils the ether…The three ethers of formula C₄H₁₀O are methoxypropane, ethoxyethane and 2-methoxypropane… →

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