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Exercise · Q14

Q.What is mutarotation? Briefly explain why pure α\alpha-D-glucose and pure β\beta-D-glucose, dissolved separately in water, both end up showing the same equilibrium optical rotation.

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Mutarotation is the phenomenon in which the specific optical rotation of a freshly prepared aqueous solution of a pure sugar anomer gradually changes over time until it settles at a fixed, constant value.

It happens because the cyclic ring form of glucose is in a dynamic equilibrium with the open-chain form: the ring can reopen (via the reverse of the hemiacetal-forming reaction) back to the open-chain aldehyde, and then reclose again, potentially forming either the α\alpha- or the β\beta-anomer at random, regardless of which anomer it started as. When pure α\alpha-D-glucose is dissolved in water, some of it opens and recloses as β\beta-D-glucose, and vice versa for pure β\beta-D-glucose dissolved separately; both starting solutions keep interconverting until they reach the very same equilibrium mixture of roughly 36% α\alpha-anomer and 64% β\beta-anomer (with only a trace of open-chain form present at any moment). Since that final equilibriu …

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