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The document outlines the synthesis of dibenzalacetone (DBA) through a base-catalyzed Claisen–Schmidt condensation of benzaldehyde and acetone. It details the reagents, apparatus, and stepwise experimental procedure, including critical observations and precautions for optimal yield and purity. Characterization methods such as melting point, IR spectrum, and NMR are also provided to confirm the product's identity.

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bhatsagar06
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4 views3 pages

Practical

The document outlines the synthesis of dibenzalacetone (DBA) through a base-catalyzed Claisen–Schmidt condensation of benzaldehyde and acetone. It details the reagents, apparatus, and stepwise experimental procedure, including critical observations and precautions for optimal yield and purity. Characterization methods such as melting point, IR spectrum, and NMR are also provided to confirm the product's identity.

Uploaded by

bhatsagar06
Copyright
© All Rights Reserved
We take content rights seriously. If you suspect this is your content, claim it here.
Available Formats
Download as PDF, TXT or read online on Scribd

Aim: To synthesize dibenzalacetone (DBA) via base-catalyzed Claisen–Schmidt

condensation of Benzaldehyde with Acetone, followed by purification and characterization.

Reagent Quantity (Typical Lab Scale) Purpose


Benzaldehyde 10 mL (~0.1 mol) Aromatic aldehyde
Acetone 5 mL (~0.07 mol) Ketone
Sodium hydroxide (NaOH) 10% aq. (20 mL) Base catalyst
Ethanol (95%) 20–30 mL Solvent
Distilled water As required Washing
Apparatus:

Conical flask, magnetic stirrer, ice bath, Büchner funnel, vacuum filtration setup, thermometer.

Principle (Mechanistic Context)

A crossed Aldol condensation occurs where:

Acetone forms an enolate under basic conditions (NaOH/KOH)

The enolate attacks benzaldehyde (no α-H → prevents self-condensation)

Dehydration yields α,β-unsaturated ketone

Second condensation produces dibenzalacetone

Experimental Procedure (Stepwise)

Step 1: Reaction Setup

Take 20 mL ethanol in a 250 mL conical flask

Add 10 mL benzaldehyde

Add 5 mL acetone

Cool the mixture in an ice bath (20–25°C control recommended)

Step 2: Base Addition

Slowly add 20 mL of 10% NaOH with constant stirring

Maintain temperature below 30°C (critical to avoid side reactions/resin formation)

Step 3: Reaction Progress

Stir for 30–60 minutes

Yellow precipitate begins forming (DBA)

Continue stirring until precipitation is complete


Step 4: Precipitation and Aging

Allow mixture to stand for 10–15 min

Optional: Chill further to improve crystallization

Step 5: Isolation

Filter using vacuum filtration (Büchner funnel)

Wash precipitate with cold distilled water until neutral pH

Step 6: Recrystallization

Dissolve crude product in hot ethanol

Allow slow cooling → crystal formation

Filter and dry at room temp or in desiccator

Observations

Stage Observation
Initial Clear solution
After NaOH addition Slight turbidity
During reaction Yellow precipitate formation
Final product Bright yellow crystalline solid

Yield Calculation

Characterization

Physical

Appearance: Yellow crystals

Melting Point: 110–112°C

Spectral Analysis

IR Spectrum:

~1660 cm⁻¹ → C=O (conjugated ketone)

~1600 cm⁻¹ → C=C aromatic/alkene


~3020 cm⁻¹ → aromatic C–H

¹H NMR:

δ 7.2–7.8 ppm → aromatic protons

δ 6.5–7.5 ppm → olefinic protons

UV-Vis:

Strong absorption ~330–350 nm (extended conjugation)

Precautions (Critical for Yield & Purity)

Maintain low temperature (<30°C) → prevents side reactions

Use fresh benzaldehyde (oxidation → benzoic acid impurity)

Avoid excess base → polymerization

Ensure slow addition of NaOH

Use cold washing to prevent product loss

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