Laboratory #1 Isolation of Carvone and Limonene from the Oil of Spearmint/Caraway Introduction The oils of spearmint and caraway are made of ch same principal components carvone, limonene, pinene but of different portions. They are used mainly in the pharmaceutical and flavor industry. Separation, Isolation, and Identification ofCarvone and Limonene The natural extract of oil will be separated to its components by using column chromatography with silica gel as stationary phase. Each fraction of eluent will be concentrated under reduced pressure to remove the solvent. The residue of each sample will be then identify using gas chromatography, mass spectrometry, and infrared spectroscopy. The separation of oils to its components will be completed by eluting the column with four different solvents in the following order: First: 30 ml petroleum ether Second: 60 ml., 19 =CH.Cl/petroleum ether Third: 25 ml, 1/4 - CH,CI/petroleum ether Fourth: 100 - 130 mL, 1/1- CH;Cl/petroleum ether Experimental Observation Fours fractions are collected corresponding to the volumes of cach solvent: Fraction A: 30 ml Fraction B: 60 ml. Fraction C: 25 ml. Fraction D: 100 – 130 ml The solvent is removed from cach fraction on the rotary evaporator. The residue mass of cach fraction is recorded. The following is observed: Residue fraction A: Probably wont yield or it will yield a very small amount. Residue fraction B: It has the first major component (assumed as pure first component). Residue fraction C: It is a mixture of the two main components Residue fraction D: It has the second major component (assumed as pure second component). Analysis and Report Analysis of Fractions: Infrared Spectroscopy and Mass Spectrometry A) From the fractions B and D, identify the functional groups using IR
Basics in Organic Reactions Mechanisms
In organic chemistry, the mechanism of an organic reaction is defined as a complete step-by-step explanation of how a reaction of organic compounds happens. A completely detailed mechanism would relate the first structure of the reactants with the last structure of the products and would represent changes in structure and energy all through the reaction step.
Heterolytic Bond Breaking
Heterolytic bond breaking is also known as heterolysis or heterolytic fission or ionic fission. It is defined as breaking of a covalent bond between two different atoms in which one atom gains both of the shared pair of electrons. The atom that gains both electrons is more electronegative than the other atom in covalent bond. The energy needed for heterolytic fission is called as heterolytic bond dissociation energy.
Polar Aprotic Solvent
Solvents that are chemically polar in nature and are not capable of hydrogen bonding (implying that a hydrogen atom directly linked with an electronegative atom is not found) are referred to as polar aprotic solvents. Some commonly used polar aprotic solvents are acetone, DMF, acetonitrile, DMSO, etc.
Oxygen Nucleophiles
Oxygen being an electron rich species with a lone pair electron, can act as a good nucleophile. Typically, oxygen nucleophiles can be found in these compounds- water, hydroxides and alcohols.
Carbon Nucleophiles
We are aware that carbon belongs to group IV and hence does not possess any lone pair of electrons. Implying that neutral carbon is not a nucleophile then how is carbon going to be nucleophilic? The answer to this is that when a carbon atom is attached to a metal (can be seen in the case of organometallic compounds), the metal atom develops a partial positive charge and carbon develops a partial negative charge, hence making carbon nucleophilic.
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