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O NUC O H C CH H C CH NUC O - The University of …
Reactions at -Position In preceding chapters on carbonyl chemistry, a common reaction mechanism observed was a nucleophile reacting at the electrophilic carbonyl carbon site O NUC O. H3C CH3 H3C CH3. NUC. Another reaction that can occur with carbonyl compounds, however, is to react an electrophile with the carbonyl O E O. H3C CH3 H3 C CH2. E. The electrophile adds to the -position and allows the synthesis of a variety of substituted carbonyl compounds by reacting different electrophiles Reactions at -Position In order to react with electrophiles at the -position, the carbonyl compound needs to be nucleophilic at the -position There are two general methods to become nucleophilic at -position: 1) React through the enol form O OH O. K Br Br 5 x 10-9 H3C CH3 H3C CH2 H3 C CH2. Br keto enol A carbonyl compound is in equilibrium with an enol Typically the equilibrium for a ketone though lies heavily in the keto form The enol form, however, is more reactive than an alkene and can undergo similar reactions as observed with reactions with bonds Reactions at -Position 2) To make a carbonyl compound even more nucleophilic at the -position, a base can be added to form an enolate O base O O.
Reactions at α-Position! The type of carbonyl compound will also affect the enolate formation! Due to the resonance stabilization of some of the carboxylic acid derivatives, !
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