we know that ethers, such as diethyl ether and tetrahydrofuran, are quite resistant to the action of dilute acids and require hot concentrated HI or HBr for cleavage. However, acetals in which two ether groups are linked to the same carbon undergo hydrolysis readily, even in dilute aqueous acid. How do you account for this marked difference in chemical reactivity toward dilute aqueous acid between ethers and acetals?

Organic Chemistry
9th Edition
ISBN:9781305080485
Author:John E. McMurry
Publisher:John E. McMurry
Chapter17: Alcohols And Phenols
Section17.SE: Something Extra
Problem 71AP: A problem often encountered in the oxidation of primary alcohols to acids is that esters are...
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we know that ethers, such as diethyl ether and tetrahydrofuran, are quite resistant to the action of dilute acids and require hot concentrated HI or HBr for cleavage.
However, acetals in which two ether groups are linked to the same carbon undergo hydrolysis readily, even in dilute aqueous acid. How do you account for this marked
difference in chemical reactivity toward dilute aqueous acid between ethers and acetals?

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