124 Messrs Jones and Kewley, Stereochemistry of Benzene. 



[M ] D for a salt of the acid with any inactive base is found to 

 be 51 "7°. The base here is therefore inactive. 



The base when recovered by the addition of potash was found 

 to be quite inactive in ethereal solution. 



1. 3. 4 methyl-chlor-amino benzene dextro-brom-camphorsulpho- 

 nate was prepared by boiling the hydrochloride of the base with 

 the requisite quantity of silver salt of Kipping and Pope's dex- 

 tro-brom-camphorsulphonic acid and some moist ethyl acetate, 

 filtering off the silver chloride and evaporating the solution to 

 dryness on a water-bath. White solid, crystallizing in fine needles, 

 very soluble in chloroform and sparingly soluble in ethyl acetate. 

 It was recrystallized repeatedly from a mixture of ethyl acetate 

 and chloroform, and it then melted at 208 — 9° C. with decom- 

 position. 



Analysis of a specimen dried in a vacuum desiccator gave the 

 following result : 



"1626 grams gave '0816 grams H 2 and "2536 grams C0 2 . 



Calculated for 

 Found. (CgHj.OH3.Ol.NH2) (C 10 H 14 BrOSO 3 H). 



C. 42-54 42 : 92 



H. 55 53 



The rotatory power was determined as in the case of the 

 dextro-camphorsulphonate. 



•292 grams in 25 c.c. gave a i) =l"38 in a 2dcm. tube, hence 

 [a] D = 591° and [M] D = 267-4°. 



"668 grams in 25 c.c. gave a D = 3 - 22° in a 2 dcm. tube, hence 

 OL, = 60-2° and [M] D = 272-9°. 



The value of [M] D for salts of the acid with inactive bases is 

 always found to be about 270°. The base here is therefore in- 

 active. 



The oil recovered from the salt was found to be quite inactive 

 when examined in ether solution. 



Unless both the salts here examined exhibit the phenomenon 

 of partial racemism, the above experiments shew that benzene 

 derivatives cannot shew optical activity due to the asymmetry 

 of a carbon atom in the ring, and that the formulae which re- 

 present the six carbon atoms of benzene as not in one plane 

 are inadmissible. 



