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Chemistry 213: Organic Chemistry Lab Nicole Celani Date: 4/3/2011 Date of Lab: 3/28/2011, 3/30/2011 Title of Lab:

Aldol Condensation Lab Part I: Introduction: The purpose of this weeks lab was to conduct an Aldol condensation reaction. This particular reaction involves the joining of acetone and benzaldehyde molecules and the loss of water. This reaction is a basecatalyzed reaction that involves a carbanion intermediate. The carbanion is known as an enolate anion in which the hydrogens on the alpha carbon are unusually acidic. The reaction is as follows.
O O O

NaOH
H

ethanol

+ 2 H2O

Part II: Experimental: (3/28/2011) Goggles and gloves were obtained for safety. Obtained 2.5 mL of benzaldehyde (d=1.05g/mL) and 0.8 mL of acetone using a syringe into a 125 mL erlenmeyer flask. Next, measured 20 mL of ethanol in a 100 mL graduated cylinder and added to the 125 mL Erlenmeyer flask. Next, obtained 25 mL of 10% sodium hydroxide solution to the 125 mL Erlenmeyer flask and added a cork. The solution was then swirled for 15 minutes. The solution immediately became a cloudy white solution and eventually turned yellow. The mixture was also slightly exothermic. Yellow crystals settled out of the solution when left to sit. A vacuum filtration apparatus was assembled and the crystals were filtered and washed with 30 mL of cold distilled water. This can be viewed in the photo to the right. The vacuum was turned off and a solution of 1 mL of glacial acetic acid and 20 mL of 95% ethanol was added to the crystals and allowed to sit for 2 minutes to ensure the crystals were washed thoroughly of acid. Next, the crystals were recrystalized from 20 mL of ethanol. The crystals were still yellow after recrystallization; this can be observed in the photo to the left. The vacuum filtration was washed and assembled. The crystals were filtered and the filter paper weight was 0.1811 grams. The weight of the vial was 13.9242 grams. The crystals were then filtered and washed with cold ethanol. Lastly, all of the materials were washed with acetone in the waste jugs and then

washed with warm soapy water and rinsed with distilled water. All materials were placed in their corresponding drawers and work area was cleaned. (3/20/2011) First, an infrared spectrum was run of the sample and can be found attached to the end lab report. The melting point range was then obtained on the melting block apparatus, 112-115C. The theoretical melting point is 112114C obtained from (http://www.guidechem.com/). The total weight of the vial and crystals after drying was 15.0552 grams. Part III: Discussion A) Data Table of weights: Weights Weight of vial Weight of Filter Paper Weight of vial and dry crystals Weight of crystals Density of benzaldehyde mL of benzaldehyde

Amounts 13.9242 g 0.1811 g 15.0552 g 1.1310 g 1.05 g/ mL 2.5 mL

Theoretical Yield: M.W. of benzaldehyde = 106.12 grams M.W. of dibenzalacetone = 234.29 grams Mole Ration: 1mole benzaldehyde: 1mole dibenzalacetone

Percent Yield: (Mass of actual yield/mass of theoretical yield) x 100 %

Experimental Melting Point: 112-115C Avg. 113.5C Theoretical Melting Point: 112-114C Avg. 113.0C http://www.guidechem.com/ Percent Difference: (E-A/A) x 100% =

Functional Groups of dibenzalacetone Functional group range peak Aromatic Ring 1660-2000 1950 weak Aromatic Ring 1450-1600 1400 strong Arene (C-H) 3030 3040 medium Alkene (C-H) 3020-3100 3000-3100 medium Alkene (C=C) 1640-1680 1650 weak Carbonyl Compound 1670-1780 1500 strong IR spectra of dibenzalacetone from Aldol Condensation Synthesis of Dibenzalacetone
Website: http://itech.pjc.edu/tgrow/2211l/aldol_instr.pdf

The Infrared Spectrum for the Product is attached to the back of the Report. Discussion B) The Aldol condensation reaction is a base catalyzed reaction in which two larger molecules are added and a smaller molecule is lost. In this particular reaction with benzaldehyde and acetone are combined to effectively lose water. The reaction began by creating a carbanion intermediate. The hydrogens present on the alpha carbon in acetone are considerably more acid than the normal alkane because the conjugate anion is stabilized through resonance with the ketone. In this reaction the hydrogen was removed by methanol acting as a base CH3O-. (Stability through Resonance)
O H H H O

HO

O C H
-

C H

+ H2O

H H H

Benzaldehyde is also in the solution with the ethanol. However, benzaldehyde is not deprotonated because it does not have protons on the alpha carbon positions. Benzaldehyde can then act as an electrophile where the newly formed anion is the nucleophile. The newly formed anion is called an enolate anion. The anion attacks the carbon in the functional group of the ketone in benzaldehyde and the elections then move up onto the oxygen. When water is reacted with this molecule the oxygen is then pronated to make an alcohol. This part of the reaction then gives of a base HO-.
O O C H
-

+
H

H2O

OH

H H H H H

+ HOThis product, -hydroxyl ketone can also react again due to the acid protons in the alpha position. When the OH- comes in and attacks the acid proton leaving a negative change in the alpha position. The molecule negative change on the alpha carbon is stabilized through resonances with the ketone.
O OH O OH C H
-

OH

HO

This intermediate can then eliminate using E1cB mechanism. In this elimination the electrons come down off the oxygen, the double bond moves over due to two many bonds to the carbon and the OH group is eliminated as the leaving group.
O
-

OH

H H

+OH-

This product is also known as a conjugated enone. The -unsaturated ketone product is favored in the configuration after elimination because the molecule is conjugated. This product, -unsaturated ketone, is still left with acid protons that can again react. The product will then react with another mole of benzaldehyde producing dibenzalacetone.
O H O H O

H H

NaOH ethanol

+ H2O

The overall mechanism for this experiment can be viewed below. Both modes of reaction of carbonyls are happening at the same time producing this product.
O O O

NaOH
H

ethanol

+ 2 H2O

The product yield for this experiment was 23% yield. Most of the loss was due to the transfer of the product throughout the experiment, mainly on the filter paper and during filtration. However, the product recovered has good evidence that it is the desired product, dibenzalacetone through chemical analysis. The melting point difference of the experimental and theoretical was only 0.4% difference giving a good indication of the desired product. This slight difference and broadness of the experimental may have been due to impurities. The IR gives significant evidence that the desired product was obtained. The Aromatic ring is observed in absorbances at 3040, 1950, 1400. The alkene absorbed at 3100-3000 and 1650. The carbonyl absorption is present in a strong absorption at 1500. These observations can be better viewed on the IR spectra attached to the lab report or in the chart in the data section of the lab report.

Work Cited: Table 12.1 page 425 Characteristic IR Absorptions of Some Functional Groups McMurry, John. "Organic Chemistry." Sandra Kiselica. Belmont, CA: Brooks/Cole, a division of Thomson Learning Inc., 2008.