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Another way to distill sparingly volatile compounds is by steam distillation The underlying principle of steam distillation is that an azeotrope forms with water, which has a lower boiling point than the pure compound itself For example, naphthalene has a boiling point of 218 C, but in the presence of steam an azeotrope is formed, which contains 16% naphthalene and boils at 99 C In addition, the continual physical displacement of the head space by water vapor aids in the collection of slightly volatile components The method of sublimation is identical in principle to distillation, the only difference being that the material to be puri ed is a solid For example, potassium tert-butoxide (KOtBu) is a solid at room temperature (mp 257 C), but at 1 torr it can be sublimed at 220 C Because most sublimations are carried out under vacuum at high temperature, the necessary safety requirements limit the availability of large apparatus Further, since the cooling surface is quickly covered with solid unlike a distillation, in which the liquid is removed from the condensor by gravity the amount of material recoverable from a single sublimation tends to be small
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RECRYSTALLIZATION
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Chromatography is the most versatile method of puri cation, and distillation the most common, but recrystallization is the most elegant Unfortunately, it is also the hardest to master and the most poorly comprehended by the beginning experimentalist In essence, the principle is quite simple: coax one compound out of solution while leaving any impurities or byproducts dissolved, then separate the newly formed crystals from the solution
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Consider a 10 g sample of a substance (Compound A) which is contaminated with a 5% impurity (Compound B) Another way to express this is to say that we have a mixture of 95 g Compound A and 05 g Compound B For the sake of discussion, let us say that both compounds happen to have the same solubility characteristics in methanol: 20 g /L at room temperature and 400 g/L at the boiling point of methanol Therefore, 25 mL of boiling methanol should be suf cient to completely dissolve the sample, since it would have the capacity to dissolve 10 g of each substance (400 g/L 0025 L = 10 g) After the solution has cooled to room temperature, however, the methanol can only hold 05 g in solution (20 g /L 0025 L = 05 g) Inasmuch as 05 g of each compound remains dissolved, 90 g of Compound A and none of Compound B should be present as a precipitate Thus, by simple ltration of this mixture Compound A can be obtained in pure form and 95% recovery (90 g recovered / 95 g originally = 095) With this example in mind, it is easy to see that recrystallization works best if the sample is already relatively pure Since Compound B is present in comparatively small amounts, its concentration is signi cantly lower than that of Compound A In fact, paradoxically, we can sometimes remove a less soluble component by this method if it is present in small enough quantity However, if we were presented with a 1:1 mixture of the compounds described above, the situation would not have been so straightforward
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CHAP 11: ORGANIC CHEMISTRY
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PART IV CHARACTERIZATION OVERVIEW
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The process of characterization is facilitated by several powerful analytical protocols We will examine ve of the more frequently encountered techniques, which can be divided into two broad categories For example, Table 117 summarizes three nondestructive analytical methods based on absorption spectroscopy that is, the interaction of light with matter There are also two destructive methods (Table 118) that are still workhorses of structure determination and while the sample is sacri ced for the analysis, the methods only require milligram quantities
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Table 117 Methods of nondestructive electromagnetic spectroscopy Method UV-Vis IR NMR Transition observed electronic vibrational nuclear spin ip Absorption range 200 800 nm 600 4,000 cm 1 25 1,000 MHz (instrument-dependent) Provides information about extended systems functional groups skeletal framework and 3-dimensional arrangement of atoms
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