302 THE ACTION OF ORGANO-MAGNES1UM COMPOUNDS 



the following investigation I have endeavored to study more 

 minutely the behaviour of quinone with G-rignard's reagents, 

 methylmagnesium iodide, ethylmagnesium bromide and 

 phenylmagnesium bromide. 



EXPERIMENTAL. 

 Quinone and Methylmagnesium Iodide. 



5 grams of clean magnesium ribbon were placed in a 500 

 c.c. flask. The flask was fitted to a reflux condenser, and 30 

 grams of methyl iodide, dissolved in 40 grams of absolute 

 ether, slowly added through the condenser. Immediately a 

 reaction set in, which was moderated by cooling the flask. 

 When the reaction was about complete, the flask was warmed 

 on a water-bath for an hour. An ethereal solution of 10 grams 

 of quinone was then added, 5 c.c. at a time, with constant 

 shaking, waiting each time until the reaction somewhat 

 abated. The saturation point was obtained by noting when 

 no precipitate formed on the addition of the quinone solution 

 to a test-tube containing a portion of the ethereal solution 

 taken from the flask. On addition of quinone, a violent 

 reaction took place, accompanied by a cracking noise ; the 

 reaction product precipitated as a green amorphous mass 

 insoluble in ether. With the object of moderating the 

 reaction, the experiment was repeated, the ethereal solution 

 being this time kept in a freezing mixture (-8G) , with, how- 

 ever, the same results as obtained at ordinary temperature ; 

 one molecule of quinone united with two molecules of methyl- 

 magnesium iodide. The methylmagnesium iodide quinone 

 compound was found impossible to isolate ; it was either 

 insoluble or the solvent caused decomposition. 



After allowing the quinone mixture to stand over night, 

 75 c.c. of cold water and dilute hydrochloric acid enough to 

 acidify the solution were added. No change of colour was 

 apparent on addition of the water, but the acid changed the 

 mixture brown and precipitated a brown flocculent precipitate. 



