Research techniques in organic chemistry by Robert Brown Bates; John Paul Schaefer

By Robert Brown Bates; John Paul Schaefer

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Certain polar aprotic solvents such as dimethyl sulfoxide, dimethylformamide, and sulfolane efficiently solvate cations but not anions; as a result, bases and nucleophiles exhibit increased basicity and nucleophilicity in these solvents. , ester formation, enamine synthesis, dehydration of hydrates). Under these circumstances, selection of a solvent such as benzene or carbon tetrachloride permits the rapid removal of the water on a continuous basis by azeotropic distillation (see Sec. 3). An ideal solvent should be inexpensive, easily purified, readily separable from the reaction products, and inert to the reagents that are employed.

Phenylhydrazine formation is detected by measuring the ultraviolet spectrum of the solution via the quartz cell. Over the course of a few houTS, the spectrum changes from that of phenyldiazene to that of phenylhydrazine. 3 Reactions Aided by Azeotropic Distillation: In many organic reactions, the starting materials are nearly as stable thermodynamically as the products; to obtain a good yield, it is necessary to force the equilibrium to the right by removing one of the products (not necessarily the desired one).

Genation of milligram to gram quantities is shown in Fig. 1-11. f When the apparatus in Fig. 1-11 is used, the catalyst, solvent, and a Teflon-covered stirring bar are placed in the special Erlenmeyer flask. After making sure that the gas burettes are filled with liquid (usually water) from the leveling bulbs and with stopcocks B, C, and E closed and D open, the system is alternately evacuated and flushed with hydrogen (ca. three times) by manipulating stopcock A. The appropriate burette is then filled with hydrogen, stopcock A is closed, and the catalyst is reduced (if necessary) and saturated with hydrogen by stirring for a few minutes.

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