Aldol condensation of 4thio2oxoselenazolidine 30a occurs at the 5position equation 4 to yield the arylidene derivatives 30bf using a catalytic amount of 25% aqueous methylamine in acetic acid. Williamson, macroscale and microscale organic experiments, 2nd ed. Two moles of benzaldehyde condense with one mole of acetone to give dibenzalacetone. Preparation of dibenzalacetone by the aldol condensation 1483 words 6 pages. Download file to see previous pages under basic conditions, the carbonyl group of acetone having an alpha hydrogen atom is converted to an enolate ion mc murry, 1999, pp.
Students may perform two or three chalcone syntheses if time permits. Experiment 15 preparation of dibenzalacetone in this experiment we will prepare dibenzalacetone from acetone and two equivalents of benzaldehyde under basic conditions. Synthesis and characterization of dibenzalacetone tan yong jie m15604 escaped into the filtrate. The reaction of an aldehyde with a ketone employing sodium hydroxide as the base is an example of a mixed aldol condensation reaction. The aldol addition reaction involves the addition of. Dibenzalacetone by aldol condensation 46 procedure. Synthesis of dibenzalacetone by aldol condensation of. Aldol synthesis of dibenzalacetone, an organic screen. Using the caboncabon bond making ability in carbonyl chemistry, dibenzalacetone is synthesized from 2 equivalent of benzaldehyde and 1 equivalent of acetone in a base catalyzed reaction. In this experiment, you will perform a type of basecatalyzed crossed aldol condensation called the claisenschmidt reaction. Preparation of dibenzalacetone by aldol condensation adapted from williamson, 5th ed. An aldol condensation is a condensation reaction in organic chemistry in which an enol or an enolate ion reacts with a carbonyl compound to form a. Synthesis of dibenzalacetone by the aldol condensation cram.
They are asked to design a synthesis of their target based on the model reaction and to modify the model reaction so it will work for. Synthesis of dibenzalacetone by the aldol condensation. Synthesis of dibenzalacetone by aldol condensation free download as word doc. For example, in the aldol condensation shown in figure 1, two molecules of ethanal are reacted to produce an a,bunsaturated aldehyde and water. The general basecatalysed reaction is shown in scheme 1. Allow the solid to air dry by continuing to apply the vacuum for 23 min.
Under the reaction conditions in the experiment, two equivalents of aldehyde will react. Observe the spot in uv light and record the r f of benzaldehyde. The benefit of this lab was to acquaint oneself with the fundamentals of the aldol condensation reaction by demonstrating the synthesis of dibenzalacetone trans, trans1,5diphenyl1,4pentadien3one through the aldol condensation of acetone with benzaldehyde. Groups of students are assigned target molecules of the dibenzalketone type and are given a sample procedure for the parent dibenzalacetone reaction. The aldehyde carbonyl is more reactive than that of the ketone and therefore reacts rapidly with the anion of the the ketone to give a. A modification of a classic experiment is described that incorporates a discovery approach to organic synthesis. Dibenzylideneacetone is used as a component in sunscreens and as a ligand in organometallic chemistry it was first prepared in 1881 by the german chemist rainer ludwig claisen 18511930. Collect this solid via hirsch filtration and wash it several times with small portions of cold water. Aldol condensation remains one of the most versatile, effective, and cheap methods for cc bond formation in organic synthesis, widely employed in industry for the preparation of indigo dye as. For example, in the aldol condensation shown in figure 1, two molecules of ethanal are reacted to produce an. Aldol condensation an overview sciencedirect topics. In this video the synthesis of dibenzalacetone is shown and the mechanism of the reaction is explained.
Dibenzalacetone by aldol condensation 45 aldol synthesis of dibenzalacetone, an organic screen overview. Higher concentrations of base give added difficulty in washing. This experiment involves condensating propanone with two steps of benz aldehyde giving dibenzalacetone. This is an example of a crossed aldol or mixedaldol reaction. Sufficient alcohol is used to dissolve the benzaldehyde rapidly and to retain the benzalacetone in solution until it has had time to react with the second molecule of aldehyde. Synthesis of dibenzalacetone by sandy thea san carlos on prezi. Lower concentrations of base slow up the formation of the dibenzalacetone and thus favor side reactions which yield a sticky product. Preparation of dibenzalacetone 1,5diphenyl1,4pentadien3one objectives performing an aldol condensation seeing how a molecule like acetone with two alphacarbons can be used to bridge an aldehyde benzaldehyde in two reaction steps. It is a paleyellow solid insoluble in water, but soluble in ethanol. The preparation of dibenzal acetone is an example of claisenschmidt reaction. Figure 2 shows the reaction of an aldehyde with a ketone employing sodium. Introduction in an aldol condensation, two molecules of aldehyde or ketone are joined together along with the loss of water. Accomplishing the synthesis of dibenzalacetone by using. Preparation of dibenzalacetone 1,5diphenyl1,4pentadien3one 2006, is.
Dibenzalacetone was successfully synthesised with a yield of. Dibenzylideneacetone or dibenzalacetone, often abbreviated dba, is an organic compound with the formula c 17 h 14 o. Synthesis of analogeous dibenzalacetone by reacting acetone and benzaldehyde and its derivatives is a wellknown reaction. Preparation of dibenzalacetone by the aldol condensation. Chalcone can be prepared by an aldol condensation between a aldehyde. Thus, it can be concluded that the product is sufficiently pure but not 100% pure. The aldol condensation preparation of 4methoxybenzalacetone.
Preparation of dibenzalacetone by a double aldol condensation. In this experiment we will prepare dibenzalacetone from acetone and two equivalents of benzaldehyde under basic conditions. To prepare a sample of dibenzalacetone theory the preparation of dibenzal acetone is an example of claisenschmidt reaction. The original product, benzalacetone, contains a set of alphahydrogens which can be used to e ect. Remember to perform steps according to logbook and be more careful. The synthesis of dibenzalacetone is an illustration of a assorted aldol condensation reaction. Preparation of dibenzalacetone by the aldol condensation david o neill date of experiment. Experimental solution preparation and tlcs into a mediumsized test tube, add 4 ml of 3 m naoh solution. Using a pipette, a drop is taken from the reaction mixture or from the product and diluted with 10 ml dichlormethane. This reaction takes place between aromatic aldehydes and aliphatic ketones in presence of sodium hydroxide. The preparation of dibenzalacetone 1,5diphenyl1,4pentadien3one is an example of an aldol condensation in which the ketone, acetone, possesses two sets, albeit equivalent, of alphahydrogens. Dibenzalacetone and its derivatives will show antimicrobial and antioxidant activity. Dibenzalacetone will crash out of the solution as a solid during the course of the reaction. The enolate ion thus produced is a strong nucleophile and attacks the carbonyl group of the accepting partner, which in this case is benzaldehyde mc murry, 1999, pp.
The synthesis began by using a strong base to generate the acetone enolate ion. This is an example of a crossedaldol or mixedaldol reaction. Crossed aldol condensation synthesis of dibenzalacetone 1,5diphenyl1,4pentadien3one introduction in this experiment, you will perform a type of basecatalyzed crossed aldol condensation called the claisenschmidt reaction. Synthesis of dibenzalacetone 1,5diphenyl1,4pentadien3one introduction. Synthesis of dibenzalacetone by aldol condensation aldehyde. Novel synthesis of 1,5dibenzalacetone using naohzro2. Synthesis of dibenzalacetone by the aldol condensation anna shahrour jocelyn barraza ta yong wang section 5 introduction aldol condensation an aldol condensation is an organic reaction in which an enol or an enolate ion reacts with a carbonyl compound to form a.
The original product, benzalacetone, contains a set of alphahydrogens which can be used to effect another nucleophilic substitution onto a second. This allows the reaction to reach completion in a reasonable amount of time. Alternatively, students can work in groups of three where each student performs a unique chalcone synthesis. Preparation of dibenzalacetone 1,5diphenyl1,4pentadien3one 2006, is 107c, which is located in that range. The reaction of an aldehyde with a ketone employing sodium hydroxide as. Synthesis of dibenzalacetone occurs via an aldol condensation reaction in fig. Pdf on oct 1, 2012, sri handayani and others published novel synthesis of 1,5 dibenzalacetone using naohzro2montmorillonite as cooperative catalyst. This experiment is an aldol condensation of two molecules of benzaldehyde with acetone to form dibenzalacetone. Preparation of dibenzylideneacetone dibenzalacetone. Recrystallize the solid by dissolving in 2 ml of hot ethanol.
The reaction is catalyzed more commonly by a base or some times by an acid. Preparation of dibenzylideneacetone dibenzalacetone from k. Dibenzalacetone is a yellow solid, which has found use in commercial sunscreen ointments. The reference melting point temperature, as according to donald l. Dibenzalacetone can be prepared by condensation of 1 mole of acetone with two moles of benzaldehyde. Dibenzalacetone is readily prepared by condensation of acetone with two equivalent of benzaldehyde. Mixed aldol condensation preparation of dibenzyalacetone introduction like the grignard reaction, the aldol condensation is an extremely useful carboncarbon bondforming reaction in organic chemistry. You will do a double mixedaldol condensation reaction between acetone and benzaldehyde. These solutions should remain inactive after preparation, but react when combined.
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