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Synthesis of Dibenzalacetone by Aldol Condensation


The aldol condensation is a reaction between two aldehydes or ketones, catalyzed by a base or acid, generating a molecule having both alcohol and aldehyde functional groups. The aldol product is either a β-hydroxyaldehyde or a β-hydroxyketone. This reaction is an important synthetic mechanism that produces large molecules through the formation of carbon-carbon bonds. The product results from the addition of one molecule of an aldehyde or ketone to a second molecule in such a way that the α-carbon of the first molecule becomes attached to the carbonyl carbon of the second molecule.

Conjugation of the newly formed double bond with the carbonyl group stabilizes the unsaturated product and provides the thermodynamic driving force for the dehydration process. The overall two-step sequence of reactions involves aldol formation and dehydration.

The steps involve an acid-base reaction between a strong base such as the hydroxide ion and a hydrogen located α to a carbonyl group of the aldehyde or ketone. The acidity of the organic species is large relative to most hydrogens that are bonded to carbon due to the resonance stabilization of the enolate that is formed. The enolate attacks the carbonyl group and the aldol undergoes an acid-base reaction with the remaining acidic α-hydrogen, followed by the loss of OH as a leaving group to give an enol. The net loss of H+ and OH represents the loss of water, therefore the term aldol condensation.

In this experiment, you will run an aldol condensation between benzaldehyde and acetone. The product precipitates out of solution and can be collected by filtration. Melting temperature analysis will be used to characterize the product.


In this experiment, you will

  • Perform an aldol condensation between benzaldehyde and acetone.
  • Purify the product by recrystallization.
  • Characterize the product by melting temperature analysis.

Sensors and Equipment

This experiment features the following Vernier sensors and equipment.

Additional Requirements

You may also need an interface and software for data collection. What do I need for data collection?

Organic Chemistry with Vernier

See other experiments from the lab book.

1Determining Melting Temperature
2Recrystallization of Benzoic Acid and Aspirin
3Determination of a Boiling Point: Simple and Fractional Distillation
4Identifying an Unknown Analgesic by Melting Temperature and Thin-Layer Chromatography
5Separation of Organic Compounds by Acid-Base Extraction Techniques
6Understanding Polarimetry
7Identification of Organic Unknowns Using Polarimetry
8Investigating Gas Chromatography
9Fractional Distillation of Esters
10Understanding Intermolecular Forces Using a Gas Chromatograph: Enthalpy of Vaporization
11Investigating Thermodynamic Relationships of Substituted Hydrocarbons
12Extraction of Spinach Pigments and Analysis by Electronic Absorption Spectroscopy
13SN1: Synthesis of t-butyl chloride
14SN2: Synthesis of 1-bromobutane
15Observing the Reaction Kinetics of Sucrose with Polarimetry
16The Synthesis and Analysis of Aspirin
17Isolation and Epoxidation of a Natural Product: Limonene
18Synthesizing Ethyl Acetate by Fisher Esterification
19Synthesis of Dibenzalacetone by Aldol Condensation
20The Diels-Alder Reaction of Anthracene with Maleic Anhydride
21Friedel-Crafts Acylation of Ferrocene
22Grignard Formation of Crystal Violet
23Synthesis of Fluorescein
24Synthesis of Methyl Orange and Its Application to Textiles
25Analysis of Natural Products
26Using a Gas Chromatograph: Identifying an Unknown Compound

Experiment 19 from Organic Chemistry with Vernier Lab Book

<i>Organic Chemistry with Vernier</i> book cover

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