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

Pair every alkyl group of one carbon with every alkyl group of four carbons…

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

Pair every alkyl group of one carbon with every alkyl group of four carbons. Then pair every group of two carbons with every group of three carbons. This gives the ethers of formula $\text{C}_{5}\text{H}_{12}\text{O}$ . There is 1 methyl group, 1 ethyl group, 2 propyl groups (propyl and isopropyl) and 4 butyl groups (butyl, isobutyl, sec-butyl and tert-butyl). Find the number of ethers, the number of alcohols (8) plus ethers, and the number of ethers that have a stereocentre.

Need a reminder? The key ideaShow

The number of ethers of $n$ carbons is the number of unordered pairs of alkyl groups with $n$ carbons in all. The Williamson synthesis needs a methyl or primary halide. Two alcohol molecules give one ether and one water. Yield $= \dfrac{\text{actual}}{\text{theoretical}} \times 100$ .

The worked solution

Have you tried it?

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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