Problem

Two structures for the sugar glucose are shown on page 858. Interconversion of the open-...

Two structures for the sugar glucose are shown on page 858. Interconversion of the open-chain and cyclic hemiacetal forms is catalyzed by either acid or base.

(a) Propose a mechanism for the cyclization, assuming a trace of acid is present.

(b) The cyclic hemiacetal is more stable than the open-chain form, so very little of the open-chain form is present at equilibrium. Will an aqueous solution of glucose reduce Tollens reagent and give a positive Tollens test? Explain.

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