O O HO, H 2 O. OR (2) One of the pair must form an enol MUCH more easily than the other

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1 Carbonyl Condensation Reactions (Conjugate Addition) If we look at resonance structures for conjugated carbonyl compounds (often called α,β-unsaturated compounds), we ll see that there are TW sites for nucleophilic attack. Thus, we ll find that the alpha carbon is often quite nucleophilic and the β carbon is electrophilic. Addition of a nucleophile to the double bond to form an enolate, which tautomerizes to the ketone, is called conjugate addition. When carbonyl addition or conjugate addition will occur? In other words, when will a nucleophile add to the carbonyl, or the double bond of a conjugated carbonyl compound? We have seen that hard nucleophiles, such as present in RMgBr and RLi reagents, add to the carbonyl. A way to force only conjugate addition with an organometallic reagent is to form the copper salt - in this case, a dialkylcuprate. We ve already seen these are used to prepare ketones from acid chlorides formation of copper salts is a great way to soften a hard nucleophile. Thus, soft nucleophiles favor conjugate addition to α,β-unsaturated compounds. ence non-carbon nucleophiles like nitrogen (amines) and oxygen (alcohols) will always add in a conjugate fashion, particularly if the reaction is carried out under neutral conditions. Some examples: Enolates are also soft nucleophiles and hence add to conjugated carbonyls in conjugate fashion. Aldol Reaction Two molecules of an aldehyde or ketone react with each other in the presence of base to form a β-hydroxy carbonyl compound: 1

2 , + In this reaction, an enolate is the nuclophile; one aldehyde molecule becomes the enolate while the other molecule serves as the electrophile. With aldehydes, the equilibrium usually favors the aldol products. But with ketones, the equilibrium usually favors starting materials. f course, there are ways to derive the equilibrium towards products in either case. You should also note that any carbonyl compound with alpha hydrogens can undergo the aldol reaction (i.e. esters, acids, etc.). ow can we tell whether a molecule is going to undergo an aldol-like reaction, or an enolate-like reaction? There are a couple of clues: 1) STRNG base. If bases like LDA are being used, and a decent electrophile is present, then you re likely looking at an enolate type reaction. ) GD electrophiles. If there s another strong electrophile around, such as a halogen molecule (Br, for example), or something like iodomethane (C 3 I), you re looking at an enolate type of reaction. 3) Catalytic amounts of a weak base. If there are no other electrophiles added, then the use of a weaker base, such as sodium ethoxide (NaEt) or hydroxide (-) is usually a clue that an aldol-type reaction will be taking place. Aldol Condensation β-ydroxy carbonyl compounds formed in the aldol reaction dehydrate more readily than other alcohols. In fact, under basic conditions, the β-hydroxy carbonyl compound is often not isolated; it loses elements of from the α and β carbons to form an α,β-unsaturated compound. For example,

3 As you see, the ene-al is simply the aldol product minus the elements of water - a condensation reaction. In fact, elimination of water is spontaneous and the β-hydroxy carbonyl compound is not isolated when the α,βunsaturated product is further conjugated with a C=C or a benzene ring:, Ph Ph Ph C 3 C 3 - Ph 3 C Ph NT ISLATED So, one more time... the aldol condensation takes a carbonyl compound (usually an aldehyde, ketone or ester) and joins two of them together to form a conjugated carbonyl compound. Generally, with aldol condensations you are combining two of the same molecule to form a dimer. owever, in a few cases it is possible to combine two different molecules to form the aldol product. There are two MAJR restrictions: (1) ne of the pair must not have any enolizable (i.e. alpha) protons (for example, aryl aldehydes & ketones like benzaldehyde or benzophenone). Et R () ne of the pair must form an enol MUC more easily than the other Claisen Condensation But what about the enolates of other carbonyl compounds, such as esters? Do they undergo these self-condensation reactions as well? f course they do! owever, the thing to note is that esters have essentially a leaving group attached to the carbonyl carbon. Thus, the products of the condensation reaction are slightly different. In essence, the product of an aldol-type reaction between two esters is almost always a 1,3-dicarbonyl compound. In its simplest form: 3

4 (note - why do we use NaEt, and not Na?). Again, this is a fairly general reaction just about any ester can undergo this type of self-condensation. The driving force of this reaction is not dehydration, however it is the formation of the stable enolate anion (i.e. the one between the two carbonyl groups) that makes the final step irreversible. Is it possible to do mixed Claisen reactions? f course, provided the same rules are followed as for the mixed aldol. ne component must either have no enolizable protons, or must be enolized VERY rapidly. Mechanism Practice!!! Draw the mechanism for the reaction above. Micheal Addition The nature of the electrophile is also worth considering. What if we have a conjugated carbonyl compound? Recall that we then add a stabilized nucleophile to the alkene portion a 1,4 addition. Malonates and keto-esters are particularly good at this type of reaction, called a Michael addition: 4

5 If a large excess of the conjugated compound is used, it is of course possible to get a double-michael (dialkylated) product: 5

Under acidic conditions, carbonyl compounds are protonated on O first, then weak base deprotonates at the α-c to give enol.

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