Even without strain hydrates and hemiacetals are

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Unformatted text preview: that carbon atom is sp3 hybridized and so there is only about ‘49° of strain.’ Not much gain, but the hydrate is more stable than the ketone. The second case is totally different. The hydroxy- aldehyde is not strained at all but the hemiacetal has ‘49° of strain’ at each atom. Even without strain, hydrates and hemiacetals are usually less stable than their aldehydes or ketones because one C=O bond is worth more than two C–O bonds. In this case the hemiacetal is even less stable and, unlike the cyclopropanone, can escape strain by breaking a C–O ring bond. Solutions for Chapter 6 – Nucleophilic Addition to the Carbonyl Group PROBLEM 3 One way to make cyanohydrins is illustrated here. Suggest a detailed mechanism for the p...
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This document was uploaded on 02/10/2014.

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