A series of dialkyl ethers was allowed to react with excess hydrogen bromide, with the fol...

A series of dialkyl ethers was allowed to react with excess hydrogen bromide, with the following results. Identify the ether in each case.

(a) One ether gave a mixture of bromocyclopentane and 1-bromobutane.

(b) Another ether gave only benzyl bromide.

(c) A third ether gave one mole of 1,5-dibromopentane per mole of ether.

Sample Solution (a) In the reaction of dialkyl ethers with excess hydrogen bromide, each alkyl group of the ether function is cleaved and forms an alkyl bromide. Because bromocyclopentane and 1-bromobutane are the products, the starting ether must be butyl cyclopentyl ether.