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Unformatted text preview: c Chemistry 2e PROBLEM 2 Cyclopropanone exists as the hydrate in water but 2- hydroxyethanal does not exist as the hemiacetal. Explain. O H2O HO O OH HO H × H O OH Purpose of the problem To get you thinking about equilibria and hence the stability of compounds. Suggested solution Hydration is an equilibrium reaction so the mechanism is not strictly relevant to the question, though there is no shame in including mechanisms whever you can. To answer the question we must consider the effect of the three- membered ring on the relative stability of starting material and product. All three- membered rings are very strained because the bond angles are 60° instead of 109° or 120°. Cyclopropanone is particularly strained because the sp2 carbonyl carbon would like a bond angle of 120°—there is ‘60° of strain.’ In the hydrate...
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This document was uploaded on 02/10/2014.

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