{[ promptMessage ]}

Bookmark it

{[ promptMessage ]}

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

Info iconThis preview shows page 1. Sign up to view the full content.

View Full Document Right Arrow Icon
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.
Background image of page 1
This is the end of the preview. Sign up to access the rest of the document.

{[ snackBarMessage ]}

Ask a homework question - tutors are online