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Lab 10a Isolation of Limonene

Lab 10a Isolation of Limonene - 10a Isolation of Limonene...

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10a Isolation of Limonene from Citrus Fruits Author: Holly Polk Instructor: Oleksandr Zhurakovskyi Organic Chemistry Lab 243A, Section 010 Date Work Performed: April 9, 2009 Date Submitted: April 16, 2009 Abstract This experiment uses steam distillation to isolate limonene from citrus fruit, and analyze by GC. Another part of this experiment is to measure the refractive index of the sample, and measure the optical rotation of the two enantiomers of limonene using a polarimeter. The R molecule produces a fresh citrus, orange-like scent while the S molecule is responsible for the harsh, turpentine-like lemon scent. The final limonene product had a refractive index of 1.466, the gas chromatography reading of limonene had a total retention of 0.842, and the infrared spectrometry results for limonene showed a peak at 3076.8, which is characteristic of C=C-H.
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Introduction In this lab, steam distillation is performed to isolate limonene from citrus fruit. Limonene can be found in the form of two distinct enantiomers, R (+)-limonene and S(-)- limonene. Consisting entierly of carbon and hydrogen, limonene is considered to be monoterpene oil commonly used in numerous industrial applications ranging from flavoring to fragrance application. Steam distillation is a method of transfer (volatiles to distillate) that will be used to isolate Limonene, a monoterpene. Terpenes are compounds that have high boiling points. For these compounds it is often better to lower the pressure at which such compounds are boiled rather than increasing the temperature if exposed to extreme temperatures, there is a possibility that the limonene within the citrus zest could be decomposed into isoprene units. When heated to high temperatures within the steam distillation process the limonene covaporizes with water at a much lower temperature than its boiling point, thus condensing (Padias, 80). To characterize the samples gathered within this lab five processes were implemented, GC reading, IR reading, R/S configuration, optical activity, and specific rotation: [α] = α / cl, where α is the observed rotation in degrees, c is the concentration/density, l the path length in dm (Padias, 81). To denote a sample as either R or S, one observed the four atoms attached directly to the chirality center and assigned
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Lab 10a Isolation of Limonene - 10a Isolation of Limonene...

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