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Unformatted text preview: ctrophiles) and react well with oxygen nucleophiles. Bromine, by contrast, is uncharged and unpolarized (it is a ‘soft’ electrophile) and reacts well with neutral nucleophiles such as alkenes. ■ ‘Hard’ and ‘soft’ reagents are explained on p. 357 of the textbook and revisited on p. 467. 6 Solutions Manual to accompany Organic Chemistry 2e PROBLEM 6 1,3–Dicarbonyl compounds such as A are usually mostly enolized. Why is this? Draw the enols available to compounds B- E and explain why B is 100% enol but C, D, and E are 100% ketone. A B O O 1 3 O OEt D C O O O O O O E O O O Purpose of the problem Exploring enols of different kinds of 1,3- dicarbonyl compounds – an important class of enolizable compounds. Suggested solution Compound A is mostly enol because only the enol is delocalised over five atoms. A minor reason for this particular compound is the intramolecular hydrogen bond in the enol. O O OH O OEt OH O OEt OEt O H O OEt You might also have pointed out that there is another equally good enol that has the other carbonyl group enolized. The two enols are tautomers of each other and of the keto- ester. O OH O OEt O OH OEt O OEt That compound B is completely enolized shows...
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