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Organic Chemistry 2

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Moderate

Hemiacetal Equilibrium

ORGO2-93F9DC

Which compound will have the highest percentage of the cyclic hemiacetal form (see equation below) present at equilibrium? Compounds that have both $C=O$ and $O-H$ groups often engage in cyclic (or intramolecular) hemiacetal formation. Two considerations are important: (1) the stability of the $C=O$ group, and (2) the stability of the various ring sizes.

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A

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B

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C

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D

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E

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