Sign In

Ozonolysis of Alkenes

Overview

Source: Vy M. Dong and Zhiwei Chen, Department of Chemistry, University of California, Irvine, CA

This experiment will demonstrate an example of an ozonolysis reaction to synthesize vanillin from isoeugenol (Figure 1). Ozonolysis of alkenes, an oxidation reaction between ozone and an alkene, is a common method to prepare aldehydes, ketones, and carboxylic acids. This experiment also demonstrates the use of an ozone generator and a low temperature (−78 °C) reaction.

Figure 1
Figure 1. Diagram showing the ozonolysis of isoeugenol to vanillin.

Procedure
  1. Add 200 mg of isoeugenol, 15 mL of MeOH, and ~ 2 mg of Sudan III to a 3-necked 50- mL round bottom flask equipped with a magnetic stir bar.
  2. Connect the reaction flask to an oxygen tank and a bubbler.
  3. Turn on the flow of oxygen.
  4. Cool the reaction mixture with a dry ice/acetone bath.
  5. Switch on the ozone generator, which converts the oxygen from the tank to ozone that goes into the reaction flask. The generator will be between the oxygen tank and the reaction flask. Allow the reaction mixture to st

Log in or to access full content. Learn more about your institution’s access to JoVE content here

Results

Vanillin was obtained as a white solid (150 mg, 76% yield); m.p. 76-79 °C; 1H NMR (400 MHz, CDCl3) δ 9.82 (br s, 1H), 7.43-7.41 (m, 2H), 7.04 (d, J = 8.8 Hz, 1H), 6.30 (s, 1H), 3.96 (s, 3H).

Log in or to access full content. Learn more about your institution’s access to JoVE content here

Application and Summary

In this experiment, we have demonstrated the synthesis of vanillin from isoeugenol using the ozonolysis reaction. Also, using an ozone generator while performing a low temperature reaction was shown.

Ozonolysis is a useful reaction to prepare aldehydes, ketones, and carboxylic acids from alkenes. It has been applied in natural product synthesis and industrial-scale preparation of pharmaceuticals. Artemisinin is a potent antimalarial agent and was one of the nat

Log in or to access full content. Learn more about your institution’s access to JoVE content here

Tags
OzonolysisAlkenesOxidationUnsaturated BondsOzoneCarbonyl ProductsAlkynesHydrazonesOrganic Chemistry ResearchNatural Product SynthesisIndustrial scale SynthesisPharmaceuticalsProcedureApplicationsCycloadditionMolozonideCarbonyl OxideCarbonylFragmentsOzonideWorkup ConditionsKetoneCarboxylic AcidAldehydeIndicator

Skip to...

0:00

Overview

0:46

Principles of Ozonolysis

2:35

Ozonolysis of Isoeugenol

3:51

Reductive Workup to Vanillin and Characterization

5:17

Applications

6:26

Summary

Videos from this collection:

article

Now Playing

Ozonolysis of Alkenes

Organic Chemistry II

66.1K Views

article

Cleaning Glassware

Organic Chemistry II

120.8K Views

article

Nucleophilic Substitution

Organic Chemistry II

97.8K Views

article

Reducing Agents

Organic Chemistry II

42.5K Views

article

Grignard Reaction

Organic Chemistry II

147.6K Views

article

<em>n</em>-Butyllithium Titration

Organic Chemistry II

46.9K Views

article

Dean-Stark Trap

Organic Chemistry II

97.1K Views

article

Organocatalysis

Organic Chemistry II

16.3K Views

article

Palladium-Catalyzed Cross Coupling

Organic Chemistry II

33.2K Views

article

Solid Phase Synthesis

Organic Chemistry II

40.0K Views

article

Hydrogenation

Organic Chemistry II

48.0K Views

article

Polymerization

Organic Chemistry II

89.7K Views

article

Melting Point

Organic Chemistry II

145.2K Views

article

Infrared Spectroscopy

Organic Chemistry II

205.1K Views

article

Polarimeter

Organic Chemistry II

97.9K Views

JoVE Logo

Privacy

Terms of Use

Policies

Research

Education

ABOUT JoVE

Copyright © 2025 MyJoVE Corporation. All rights reserved