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Www.IonsClub.Com The official website of Pharmacy college in the SIUST
Syrian International Private University For Science & TechnologyProvides you with this report of one of the practical experiment inorganic chemistry laboratory
 
Aldol Condensation
Under the influence of base or dilute acid, two molecules of an aldehyde or a keton may combine to form a
β
-hydroxy ketone. This reaction is called the
aldol condensation.
In every case the product results from theaddition of one molecule of aldehyde (or ketone) to a second molecule in such a way that the
α
-carbon of thefirst becomes attached to the carbonyl carbon of the second. For example:Until now we have gotten hydroxyl aldehyde or ketone. To reach our compound; we can get further bydehydration the product i.e. , to do double aldol condensation.The
β
-hydroxy aldehydes and
β
-hydroxy ketones obtained from aldol condensation are very easilydehydrated; the major products have the carbon-carbon double bond between the
α
- and the
β
-carbon atoms.As we can see in our experiment we have acetone and benzaldehyde:Once you look to this product you could surprise because it's different from what we talk above.Don't worry, we said before we want to do a double aldol condensation; let's talk about the mechanism tolearn how such reaction could proceeds:Our product is very simple, just we have inserted two benzal into one acetone, so we need 2 equivalentweight of benzaldehyde to do that.Before that what could happens at first:
 
You see that the hydroxide ion took the
α
-hydrogen from acetone to yield a water molecule ( the hydroxide part marked by asterisk " * " to indicate that this is the same hydroxide ion) and to yield the enolate our nucleophile, which is more basic than OH
-
.This nucleophile is very attracted by the electrophile ( the carbon of the carbonyl group ) which is the step-2.Then the enolate ion attached to the carbonyl carbon which is now sp3-hyderdized.In step-3- the oxygen got the proton from our likely hydroxide.But there is something confusing here !! why the hydroxide ion took the
α
-hydrogen rather than attack thecarbonyl carbon? Which is the likely "addition" reaction !!.Carbonyl group provides a site at which nucleophilic addition can take place. But, like the carbon-carbondouble bond and the benzene ring, the carbonyl can play another role, not as a functional group, but as asubstituent. Now we are ready to learn the other part of the story: how the carbonyl group strengthens theacidity of the
α
-carbon.But who is the predominant? The addition or the substitution to form the cabanion?Actually both reactions are possible at once, but, who is the predominant; that depends on the environment.To solve this problem let's follow up each kind of them.First, the addition :Suppose this reaction is possible, but, let's see the other one:Let's judge:Both reaction are reversible and both product could be present (the dihydroxyl product could be consider asimpurities, which is a big problem).The solution to this problem arises from this reversibility, the produced enolate is very reactive( strong nucleophile ) and once it's formed it attacks the carbonyl carbon of the banzaldehyde, by this waythe concentration of the enolate ions reduced; results in shifting the equilibrium to the right in order to adjustthat change according to
Henri
 
Louis
 
Le
 
Châtelier
principle.While the 2,2-Dihydroxyl propane there isn't any reaction could undergoes, except its hydrolysis to come back into acetone to adjust the previous changing in acetone concentration.
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