By C.H. Heathcock
Quantity 2 bargains more often than not with the addition reactions of delocalized carbanions (enolates) and their artificial family members (metalloenamines, enol ethers, allyl organometallics) with carbonyl compounds, imines and iminium ions. significant emphasis is put on C-C bond-forming reactions equivalent to the aldol and Mannich reactions. Acylation reactions also are integrated during this quantity. numerous subject matters that experience now not formerly been reviewed are coated, together with using enzymatic aldol reactions in synthesis and the Passerini-Ugi reactions.
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Extra resources for Additions to C-X &pgr;-Bonds, Part 2, Volume 2
Sample text
The central carbon atom bears eight, seven and six electrons respectively. These three species are illustrative of the principal electronic configurations that a carbon atom adopts in organic chemistry. There is one more carbon species that is encountered less frequently. Propose an equation for the production of the species that results from the loss of the X− anion from the CX3− species. Draw its dot and cross structure. h... 27/06/2006 Página 1 de 1 Page 31 In this species, the carbon atom has only six electrons accommodated around it, four of which are involved in two single covalent bonds, while the other two are not involved in bonding with other atoms.
Draw a mechanism involving the redistribution of the electrons present in all the double bonds.
Draw the product that results from the heterolytic cleavage of the carbonyl bond. The carbonyl carbon atom will exert a strong inductive effect, because it has been made slightly positive due to the −M effect of the carbonyl oxygen. More importantly though, it will also exert a strong mesomeric effect on the carbon/ carbon double bond. We saw earlier that it is through the π system that whole units of charge may be separated. Draw the result of the heterolytic cleavage of the carbon/carbon bond, and then the subsequent formation of a new carbon/ carbon double bond between the central carbon atoms.