Preparation of Dibenzalacetone by the Aldol Condensation Sample

Table of Content

Steam bath. ice bath. Buchner funnel. beaker. conelike flask. filter paper. TLC setup. Melting point setup Materials / chemicalsBenzaldehyde. propanone. ethanolic Na hydrated oxide. ethyl alcohol

IntroductionThe synthesis of dibenzalacetone is formed from an Aldol condensation reaction. An Aldol condensation reaction is a really effectual manner of organizing a C – C bond reaction. in which the enolate anion adds to the carbonyl group of the aldehyde. Aldol condensations are really versatile. as the enolate anion of the carbonyl compound can be added to the carbonyl C of another. The synthesis of dibenzalacetone is an illustration of a assorted Aldol condensation reaction. This experiment involves condensating propanone with two steps of Benz aldehyde ( giving dibenzalacetone. an organic Sun screen ) . The carbonyl group on the aldehyde is more reactive than that of the keytone. Therfore the enolate ion of Benz aldehyde adds to the carbonyl group of the propanone giving b-hydroxykeytone. This so undergoes base catalysed reaction with easiness. Depending on the measure of reactants used the reaction may bring forth glandular fever or dibenzalacetone. Because we want dibenzalacetone. 2 moles of Benz aldehyde is reacted with one mole of propanone in the presence of Na hydrated oxide.

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The reaction strategy is given by:

Procedure·Initially in the synthesis of Dibenzalacetone I mixed 5 milliliter ( 0. 049 moles ) of Benz aldehyde with 1. 8 milliliter ( 0. 0245 moles ) of propanone in a little beaker. ·I so added half of this mixture to 90 milliliter of ethanoic Na hydrated oxide in a 100 milliliter conelike flask. ·I allowed this mixture to stand for 15 mins.

·I so placed the balance of the old aldehyde- keytone mixture into this conelike flask and swirled the solution for 30 mins. ·The merchandise was collected under suction utilizing the Buchner funnel and the suction pump. ·The collected merchandise was so washed with 3 tens 100 milliliters of H2O to take all hints of Na hydrated oxide. ·Using filter paper I dried the merchandise every bit much as possible by pressing it into the paper utilizing my spatula. ·The merchandise was recrystallized signifier ethyl alcohol ( 10 Master of Library Science of ethyl alcohol of every 4 g of dibenzalacetone ) ·I carried out the TLC analysis of dibenzalacetone and recorded the thaw point by utilizing the thaw point setup. ·The per centum output was calculated and the thaw point noted.

Functional group trialSchiff’s trial for aldehydesMany aldehydes in solution on in a suspension give a ruddy coloring material with Schiff’s reagent. ·I added 1 milliliter of Benz aldehyde solution to 1 milliliter of Schiff’s reagent and assorted the two of them good. ·In the cold a pink- ruddy coloring material developed

·The pink – red coloring material indicated that the aldehyde functional group is present in Benz aldehyde. Note:·Schiff’s reagent consists of the dye rosaniline bleached with sulfurous. Acid·A negative consequence will look in the presence of keytones and besides choral hydrate Tollens Ag mirror trialTollens reagent is cut down by aliphatic and aromatic aldehydes R-CHO + Ag ( NH3 ) 2OH2Ag + RCOO-NH4+ + H2O + NH3·In this trial I added 2 beads of dilute NaOH followed by dilute ammonium hydroxide ( drop wise ) to 1 milliliter of AgNO3 until a precipitated Ag oxide is about dissolved. ·I so added 2 – 3 beads of Benz aldehyde solution to the mixture. ·The mixture was warmed gently

·A Ag mirror of metallic precipitate was formed giving a positive consequence for cut downing aldehydes. reasoning that Benz aldehyde has an aldehyde functional group. Keytones give a negative consequence.

Chemical reaction with 2. 4-DinitrohenylhydrazineNote:2. 4-Dinitrohenylhydrazine reacts with the aldehyde carbonyl group to give 2. 4-dinitrophenylhydrazones which are orange/yellow crystalline precipitates that are indissoluble in H2O. ·I added 2. 4-Dinitrohenylhydrazine reagent solution and 500 milligram of the Benz aldehyde in an aqueous solution. ·I covered the top of the trial tubing with a cork and agitate the trial tubing smartly ·A few beads of H2O were added to aid precipitation.

Hydroxylamine hydrochloride trialTo 1mL of aldehyde solution I added 2-3 milliliter of hydroxylamine hydrochloride reagent solution with 2 beads of methyl orange solution. The mixture was warmed gently.After a few proceedingss a ruddy coloring material had developed.

Consequences and informationsMelting pointThe runing point of dibenzalacetone was determined utilizing the thaw point setup. The runing point was found to be 108°C. the crisp thaw point scope indicates that the dibenzalacetone produced was really pure. Percentage output

Percentage output of pure dibenzalacetoneConcluding mass = 4. 268 gTheoretical output = 0. 0245 MDibenzalacetone 1M = 234. 3 gTherefore 4. 268 g = 0. 0182 MTheoretical output = 0. 0245 due to the 1:1 ratio in the reaction strategy. Percentage output = existent output obtained ( M ) / theoretical output ( M ) x 100 Percentage output = 0. 0182/0. 0245 ten 100 = 74. 3 %Purification analysisMelting point findingThe efficaciousness of a recrystallisation can be concluded by a thaw point. A pure compound normally has a crisp and characteristic thaw point. Even little sums of dross may deject the thaw point greatly. By and large. one crystallises to constant runing point. Therefore the runing point of a substance is an index of pureness and besides a specification for labelling many drug substances Thin bed chromatography

Thin bed chromatography is a really popular and widely used for of chromatography as it gives a fast. qualitative analysis of mixtures and finding of pureness of elements. The separation is carried out on a level home base coated with a thin bed of absorptive stuff ( stationary stage ) . The crystals that we were analyzing were dissolved in an appropriate dissolver and spotted on the home base at the base line. This home base is so placed in a underdeveloped jar with a small of the attractive force developing dissolver ( nomadic stage ) . The assorted compounds in the mixtures ascend the home base ( due to capillary action ) at different depending on their differing affinity for the absorbent ( mutual opposition ) . The higher up the home base the mixtures ascend the more non-polar they are. The RF values can besides bespeak the mutual opposition of the compounds. Analyzing the chromatogram

In this experiment the stuff in which we used in the TLC was colourless so to visualize the chromatogram an extremist violet visible radiation had to be used. When illuminated with an UV light the absorbent so glows a picket viridity and the organic compounds turn up as dark musca volitanss because they quench the fluorescence. Using the places of the mixtures of the TLC I calculated the RF values. RF value = distance travelled by compound/ distant travelled by solvent front RF of Benz aldehyde = 6/15 = 0. 4

RF of dibenzalacetone = 6. 4/15 = 0. 4266

Mobile stage used: ethyl ethanoate hexane in a 1:1 ratio.

DecisionIn decision I can state that in the presence of Na hydrated oxide. 2 moles of Benz aldehyde and 1 mole of propanone can be reacted to synthesise 1mole of dibenzalacetone. The synthesis gave a sensible output of 74. 3 % . The loss of the other 25. 7 % could hold been due to personal experimental mistake throughout the experiment. My purified dibenzalacetone had a liquescent point of 108°C. which indicated that the substance must be pure as the precise thaw point of dibenzalacetone is 130°C. This low border of difference between my runing point consequences and the existent thaw point can turn out the pureness of my crystals and the success of the experiment. Mentions used

School of Pharmacy and Pharmaceutical scientific disciplines research lab manual ( PH1001 ) British formularyOrganic chemical science – Heart et AlWikipedia. com

Questions1. Mechanism for the formation of benzalacetone.

Mechanism for the formation of dibenzalacetone.

2. Write the expression to demo the possible geometric isomers of dibenzalacetone. Which isomer would you happen to be the most stable and why?

The E-E isomer of dibenzalacetone is most stable because it has the highest thaw point. This tells me that it is the most stable and less volatile than the other isomers which have a lower thaw point. 3. I can state that my merchandise consists of a individual isomer because I found that my merchandise had a distinguishable thaw point. bespeaking that a pure substance was formed. The merchandise did non get down to run over a scope of different temperatures which concludes that several isomers were non present in the compound. 4. In order to synthesis benzalactone. I would:

·React 1 mole of Benz aldehyde with 1 mole of propanone. ·I would non hold a 2:1 ratio between them.In order to synthesis benzalacephonone. I would:·React 1 mole of Benz aldehyde with 1 mole of acetophenone. 5.

Harmonizing to the BP. 98 % to 101 % of the E isomer is allowed.

Harmonizing to the BP. 13 % to 18. 5 % of the Z isomer is allowed. By transporting out the thin bed chromatography it is possible to distinguish between the E and Z isomer. The TLC procedure will ensue in different RF values for each of the isomers and will let you to distinguish between them.

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Preparation of Dibenzalacetone by the Aldol Condensation Sample. (2017, Aug 13). Retrieved from

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