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Ether Cleavage Reactions

Consider the pairs of ethers, numbered 1 through 6, shown below. To the right of each pair is a description of reaction conditions to be applied to each. One compound of the pair will react more rapidly than the other. Using the buttons below the structures, select which ether of the two will be more rapidly cleaved.
In problem 4 the methyl ether is the focus of the reaction.

Ether Pairs Cleavage Conditions
1. Pair 1: isopropyl phenyl ether vs 3,5-dimethylphenyl methyl ether; cleaved with HBr in CH3CN, 40 C.
2. Pair 2: 4,4-dimethylcyclohexyl tert-butyl ether vs 4,4-diethylcyclohexyl methyl ether; H2SO4 in CH3CN, 40 C.
3. Pair 3: 3-ethylpent-3-yl phenyl ether vs bicyclic bridgehead phenyl ether; H2SO4 in CH3CN, 40 C.
4. Pair 4: 2-hydroxytetrahydropyran with methyl ether vs cyclic acetal methyl ether; 5% aqueous H2SO4, 25 C.
5. Pair 5: allyl isopropyl ether vs 1-propenyl (enol) isopropyl ether; 5% aqueous H2SO4, 25 C.
6. Pair 6: benzyl ethyl ether vs 3-phenylpropyl methyl ether; cleaved by Na in NH3(liq) then H3O+.

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