The nucleosides shown in Figs. 25.4 and 25.5 are stable in dilute base. In dilute acid, however,

Question:

The nucleosides shown in Figs. 25.4 and 25.5 are stable in dilute base. In dilute acid, however, they undergo rapid hydrolysis yielding a sugar (deoxyribose or ribose) and a heterocyclic base.
(a) What structural feature of the nucleoside accounts for this behavior?
(b) Propose a reasonable mechanism for the hydrolysis.