Synthesis of Dibenzalacetone

Synthesis of Dibenzalacetone Mixed Aldol Condensation (Claisen Schmidt) reaction between Acetone and Benzaldehyde in the presence of 95% Ethanol and 20% Sodium Hydroxide References:

Slayden Pavia

- p. 77 - p. 61 68

Schornick - http://classweb.gmu.edu/jschorni/chem318

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Synthesis of Dibenzalacetone

Overview

Synthesis of Dibenzalacetone Mixed Aldol Condensation (Claisen Schmidt) reaction between Acetone and Benzaldehyde in the presence of 95% Ethanol and 20% Sodium Hydroxide Determination of Mass, Moles, Molar Ratio, Limiting Reagent, Theoretical Yield Vacuum Filtration Recrystallization (from Ethanol) Melting Point

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Synthesis of Dibenzalacetone

Laboratory Report Synthesis Experiment Mass, Moles, Molar Ratio, Limiting Reagent, Theoretical Yield Procedures: Title Be Concise Ex. Vacuum Filtration, Recrystallization, etc. Materials & Equipment 2 Columns in list (bullet) form Note: include all reagents and principal equipment Description of Procedure: Use list (bullet) form Concise, but complete descriptions Use your own words Dont copy book!! Neat, logically designed template to present of results
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Synthesis of Dibenzalacetone

Summary

Paragraph summarizing the experimental results and computed results Analysis & Conclusions

Limiting reagent Discuss reaction mechanism in the context of your experimental results Verification of product

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Synthesis of Dibenzalacetone

The Reaction

Mol Wgt 234.29 g/mol

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Synthesis of Dibenzalacetone

Elements of the Experiment:

Determination of Mass of Reagents (two methods) Compute Moles Determine Molar Ratio, Limiting Reagent and Theoretical Yield

Note: The Molar Ratio is not 1:1

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Mix Reagents & Initiate the Reaction by swirling 1st Vacuum Filtration Recrystallization (from Ethanol) 2nd Vacuum Filtration Dry Sample Melting Point
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Synthesis of Dibenzalacetone

Reagents

Benzaldehyde Acetone Ethanol Sodium Hydroxide

2.8 mL

(27.6 mmoles or 2.93g)

1.0 mL (13.5 mmoles, i.e. < half the amount of Benzaldehyde) 15 mL 95% Ethyl Alcohol 20 mL 3 M Aqueous NaOH

Note: Acetone is intended to be the limiting reagent and is to be limited to just less than the Molar equivalent of Benzaldehyde used (see stoichiometric Molar ratio). An excess of Acetone would inhibit the Di-Substitution from taking place. Since the Aldehyde Carbonyl group is more reactive than the Acetone carbonyl and only the Acetone can form an enolate ion, only one condensation reaction is likely to occur. The Sodium Hydroxide base promotes dehydration (removal of the two water molecules).

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Synthesis of Dibenzalacetone

Procedure

To a clean, dry 125 mL Erlenmeyer Flask add:

15 mL 95% Ethanol and 20 mL 3 M Sodium Hydroxide (NaOH)

Obtain a vial of Benzaldehyde from the instructor containing approximately 2.8 mL of Benzaldehyde Weigh the vial to the nearest 0.001 g To the vial containing the Benzaldehyde, add exactly 1.00 ml Acetone from a Volumetric Pipet Weigh the vial again Use the volume & density of Acetone to determine its mass
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Synthesis of Dibenzalacetone
rocedure (Cont)

Add the contents of the vial (Benzaldehyde and Acetone) in 2 portions, with swirling, to the Erlenmeyer Flask containing the Ethanol & NaOH Swirl the mixture until a precipitation occurs, and continue the swirling until the precipitate shows signs of thickening This can take several minutes Set up the Vacuum Filtration apparatus Moisten the filter paper disk with Distilled Water Pour the contents of the Erlenmeyer flask into the Buckner funnel and perform a Vacuum Filtration Note: the filtration process must continue until the precipitate in the Buckner funnel is quite dry

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Consult instructor if the vacuum pull appears to be weak

Synthesis of Dibenzalacetone

Procedure (Cont)

Wash the crystals with two (2) 25 mL portions of Distilled Water to remove all traces of the base (NaOH) Note: The vacuum process must be complete before adding the second portion of Distilled Water

The waste from this step can be flushed down the drain Recrystallize the crude product from 10 mL Ethanol Separate the recrystallized product from the Ethanol by Vacuum Filtration Wash the product with two (2) 10 mL portions of Ethanol Note: Vacuum process must be complete for each step Place Vacuum Filtration Waste in the appropriate bottle in hood
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Synthesis of Dibenzalacetone

Procedure (Cont)

Place the Crystals from the Vacuum Filtration on a preweighed weighing tray Place the weighing tray in the class drawer and allow to dry for a week Determine the Mass of the dried product Compute percent yield Determine melting point of the product (MP Dibenzalacetone 113oC (decomposes)

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Synthesis of Dibenzalacetone

Procedure (Cont)

Report Notes:

In your report compute the Mass of Benzaldehyde by weighing the vial + Benzaldehyde and the empty vial Compute the Mass of Acetone from the Volume and Density Acetone Density 0.7857 g/mL Compute the Moles of Benzaldehyde and Acetone Benzaldehyde: MW 106.12 Acetone: MW 58.08

Set up the Stoichiometric Balanced Equation and Determine the Molar Ratio of Benzaldehyde to Acetone. Determine the Limiting Reagent based on the actual moles of Benzaldehyde and Acetone used and the Stoichiometric Molar Ratio. Note: The actual Moles of Acetone should be equal to or just less than the moles of Benzaldehyde

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