Pdf on oct 1, 2012, sri handayani and others published novel synthesis of 1,5 dibenzalacetone using naohzro2montmorillonite as cooperative catalyst. Synthesis of dibenzalacetone by aldol condensation of. Aldol synthesis of dibenzalacetone, an organic screen. Mixed aldol condensation preparation of dibenzyalacetone introduction like the grignard reaction, the aldol condensation is an extremely useful carboncarbon bondforming reaction in organic chemistry. The synthesis of dibenzalacetone is an illustration of a assorted aldol condensation reaction. It is a paleyellow solid insoluble in water, but soluble in ethanol. To prepare a sample of dibenzalacetone theory the preparation of dibenzal acetone is an example of claisenschmidt reaction. Groups of students are assigned target molecules of the dibenzalketone type and are given a sample procedure for the parent dibenzalacetone reaction.
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. 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. 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. Dibenzalacetone is readily prepared by condensation of acetone with two equivalent of benzaldehyde. Collect this solid via hirsch filtration and wash it several times with small portions of cold water. Dibenzalacetone by aldol condensation 46 procedure. Synthesis of dibenzalacetone 1,5diphenyl1,4pentadien3one introduction. Preparation of dibenzalacetone by a double aldol condensation. Preparation of dibenzalacetone by the aldol condensation. Synthesis of dibenzalacetone by the aldol condensation. 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. Synthesis of dibenzalacetone by sandy thea san carlos on prezi. The synthesis began by using a strong base to generate the acetone enolate ion. The aldol condensation preparation of 4methoxybenzalacetone.
A modification of a classic experiment is described that incorporates a discovery approach to organic synthesis. Using a pipette, a drop is taken from the reaction mixture or from the product and diluted with 10 ml dichlormethane. Students may perform two or three chalcone syntheses if time permits. Dibenzalacetone and its derivatives will show antimicrobial and antioxidant activity. Preparation of dibenzylideneacetone dibenzalacetone. Novel synthesis of 1,5dibenzalacetone using naohzro2. 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. Allow the solid to air dry by continuing to apply the vacuum for 23 min. For example, in the aldol condensation shown in figure 1, two molecules of ethanal are reacted to produce an. 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. In this experiment, you will perform a type of basecatalyzed crossed aldol condensation called the claisenschmidt reaction. This experiment is an aldol condensation of two molecules of benzaldehyde with acetone to form dibenzalacetone. Observe the spot in uv light and record the r f of benzaldehyde. This experiment involves condensating propanone with two steps of benz aldehyde giving dibenzalacetone. Synthesis of analogeous dibenzalacetone by reacting acetone and benzaldehyde and its derivatives is a wellknown reaction. Alternatively, students can work in groups of three where each student performs a unique chalcone synthesis. This reaction takes place between aromatic aldehydes and aliphatic ketones in presence of sodium hydroxide.
Experimental solution preparation and tlcs into a mediumsized test tube, add 4 ml of 3 m naoh solution. Synthesis of dibenzalacetone occurs via an aldol condensation reaction in fig. The reaction of an aldehyde with a ketone employing sodium hydroxide as the base is an example of a mixed aldol condensation reaction. 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.
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. Under the reaction conditions in the experiment, two equivalents of aldehyde will react. Two moles of benzaldehyde condense with one mole of acetone to give dibenzalacetone. Preparation of dibenzalacetone by the aldol condensation david o neill date of experiment. For example, in the aldol condensation shown in figure 1, two molecules of ethanal are reacted to produce an a,bunsaturated aldehyde and water.
You will do a double mixedaldol condensation reaction between acetone and benzaldehyde. Preparation of dibenzalacetone by the aldol condensation 1483 words 6 pages. Dibenzalacetone was successfully synthesised with a yield of. Lower concentrations of base slow up the formation of the dibenzalacetone and thus favor side reactions which yield a sticky product. Preparation of dibenzalacetone by aldol condensation adapted from williamson, 5th ed. Synthesis and characterization of dibenzalacetone tan yong jie m15604 escaped into the filtrate. Recrystallize the solid by dissolving in 2 ml of hot ethanol. Williamson, macroscale and microscale organic experiments, 2nd ed.
Synthesis of dibenzalacetone by the aldol condensation cram. The preparation of dibenzal acetone is an example of claisenschmidt reaction. The aldol addition reaction involves the addition of. 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.
This is an example of a crossed aldol or mixedaldol reaction. Aldol condensation an overview sciencedirect topics. Figure 2 shows the reaction of an aldehyde with a ketone employing sodium. 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. The general basecatalysed reaction is shown in scheme 1. The original product, benzalacetone, contains a set of alphahydrogens which can be used to e ect. Dibenzalacetone is a yellow solid, which has found use in commercial sunscreen ointments. Preparation of dibenzalacetone 1,5diphenyl1,4pentadien3one 2006, is 107c, which is located in that range. Dibenzylideneacetone or dibenzalacetone, often abbreviated dba, is an organic compound with the formula c 17 h 14 o. This allows the reaction to reach completion in a reasonable amount of time. 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. 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. The reaction of an aldehyde with a ketone employing sodium hydroxide as. 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.
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. Accomplishing the synthesis of dibenzalacetone by using. Experiment 15 preparation of dibenzalacetone in this experiment we will prepare dibenzalacetone from acetone and two equivalents of benzaldehyde under basic conditions. Synthesis of dibenzalacetone by aldol condensation free download as word doc. 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. The original product, benzalacetone, contains a set of alphahydrogens which can be used to effect another nucleophilic substitution onto a second. Dibenzalacetone can be prepared by condensation of 1 mole of acetone with two moles of benzaldehyde. The reaction is catalyzed more commonly by a base or some times by an acid. The reference melting point temperature, as according to donald l. 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. Synthesis of dibenzalacetone by aldol condensation aldehyde.604 131 345 615 1570 1040 1157 1253 553 529 54 1102 929 1161 1151 26 1565 405 1449 1120 1264 1284 1518 603 1061 1247 269 758 922 1091 313 1070 1055 593 156 1061 759 1253 1035 559 990