Dolbier HW Solutions 355

Dolbier HW Solutions 355 - 449 ALDEHYDES AND KETONES:...

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Notice that the phenyl and hexyl substituents may be either cis or trans to each other. The two prod- ucts are the cis and trans stereoisomers. 17.30 Cyclic hemiacetals are formed by intramolecular nucleophilic addition of a hydroxyl group to a carbonyl. The ring oxygen is derived from the hydroxyl group; the carbonyl oxygen becomes the hydroxyl oxygen of the hemiacetal. ( a ) This compound is the cyclic hemiacetal of 5-hydroxypentanal. Indeed, 5-hydroxypentanal seems to exist entirely as the cyclic hemiacetal. Its infrared spec- trum lacks absorption in the carbonyl region. ( b ) The carbon connected to two oxygens is the one that is derived from the carbonyl group. Using retrosynthetic symbolism, disconnect the ring oxygen from this carbon.
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This note was uploaded on 09/28/2011 for the course CHM 2210 taught by Professor Reynolds during the Fall '01 term at University of Florida.

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