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Isolation of R-(+)-Limonene from Oranges using Steam Distillation


Natural products are compounds produced by living organisms. Recently a great deal of exploration has been done involving the use of natural products in pharmaceutical drug discovery and drug design. Extraction of natural products from organisms is an important part of modern organic chemistry. One commonly performed natural product isolation is the extraction of R-(+)-limonene from the fruit of Citrus sinensis, i.e., the orange tree. This enantiomeric form of the molecule is responsible for the characteristic odor of citrus fruits.

Many natural products, like R-(+)-limonene, have chiral centers making them optically active. In this experiment, you will isolate limonene and purify it via an epoxidation reaction. Epoxidation is a key transformation in an organic chemist’s arsenal. This particular epoxidation is carried out under “green” conditions, since it uses water as the solvent. Finally, you will compare the optical purity of your product to a neat sample using polarimetry.


In this experiment, you will

  • Isolate R-(+)-limonene from oranges by performing a fractional distillation.
  • Perform an epoxidation reaction, under “green” conditions, to generate the pure R-(+)-limonene.
  • Compare the enantiomer of the synthesized limonene to neat limonene using polarimetry.

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
3Determination of a Boiling Point
4Identifying an Unknown Analgesic by Three Methods
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 of R-(+)-Limonene from Oranges using Steam Distillation
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 17 from Organic Chemistry with Vernier Lab Book

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

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