Chirality-Isolation of Limonene from Citrus Fruits

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Chirality-Isolation of Limonene from Citrus Fruits Post-lab #5 Elena Manakhova Lab group: Michele, Charlyne G. CHM2210L Introduction/Background. The roots of organic chemistry are embedded in the substances derived from natural sources. The eventual realization that these natural products could also be synthesized from nonliving materials led to the overthrow of the vital force theory and the creation of the discipline called “organic” chemistry. Essential oils make up a large group of organic compounds obtained from plants. These oils are often characterized by very distinct odors, and are dependent on a certain degree of stereochemistry found in a particular molecule. Many of these essential oils belong to a class of compounds called terpenes. When terpenes are modified chemically, such as by oxidation or rearrangement of the carbon skeleton, the resulting compounds are generally referred to as terpenoids. Terpenes are made of two or more five carbon units, named isoprene. Limonene, the chief component of orange oil, is widely used as a fragrance and flavoring, as well as a cleaning solvent. Limonene, a naturally occurring hydrocarbon, is a cyclic monoterpene, a class of natural products biosynthesized by the assembly of isoprene units into various structures. Many terpenes are responsible for the odors of plants like eucalyptus, pine, mint, lavender, rose, and others. Organic chemists use terpenes and other natural products as chiral starting materials for complex chemical syntheses or as inspirations for pharmaceuticals. Some natural products are attractive synthetic targets because of interesting or unusual structural features or medicinal applications. Carbon number four of the cyclohexane ring in limonene is chiral, it has four different groups attached to it. Limonene therefore has two optical isomers. The optical isomers are nonsuperimposable

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