Isotopic liquid ammonia

Predict the products formed when each of the following isotopically substituted denvatives of chlorobenzene is treated with sodium amide in liquid ammonia Estimate as quantitatively as possible the composition of the product mixture The astensk ( ) in part (a) designates C and D in part (b) is... 

For the exchanges carried out in liquid ammonia, kinetic isotope effects kD kT of 2.3-2.5 have been obtained for reaction of benzene, toluene, and naphthalene and for the reactions of the 2 positions of furan and thiophene with -butoxide in dimethyl sulphoxide somewhat lower values, 1.5 and 1.3, respectively, were obtained591, but whether this was a solvent or a substituent effect is not apparent from the data. 

Wilson and Dickenson observed no exchange, over a period of three hours at 100 °C, between arsenate and arsenite ions in media ranging from aqueous acid to aqueous alkali. Martin et al have found similar results for the exchange between arsenate and thioarsenite ions in aqueous media. However, in liquid ammonia exchange occurred between ammonium arsenate and arsenic trisulphide. The isotopic method was used -... 

Exchange reactions, hydrogen isotope, of organic compounds in liquid ammonia, 1, 156 Exchange reactions, oxygen isotope, of organic compounds, 2, 123 Excited complexes, chemistry of, 19,1 Excited molecules, structure of electronically, 3, 365... 

Hydrogen isotope exchange reactions of organic compounds in liquid ammonia, 1, 156... 

A solution to the question of the mechanism of these reactions was provided by John D. Roberts in 1953 on the basis of an imaginative experiment. Roberts prepared a sample of chlorobenzene in which one of the carbons, the one bearing the chlorine, was the radioactive mass-14 isotope of carbon. Reaction with potassium amide in liquid ammonia yielded aniline containing almost exactly half of its 14C label at C-l and half at C-2 ... 

Isotope exchange reactions, hydrogen, of organic compounds in liquid ammonia, 1,150 Isotope exchange reactions, oxygen, of organic compounds, 3, 123 Isotopes and organic reaction mechanisms, 2, 1... 

---