(178 } 
Chemistry. — “The intramolecular rearrangement in halogen-aceta- 
milides and its velocity”. By Dr. J. J. Buanksma. (Communicated 
by Prof. LoBry pe BRUYN). 
In a former paper *) attention was called to the fact that the ready 
bromination, nitration, sulphonation ete. of phenol and aniline deri- 
vatives may be explained by assuming that the halogen atom or the 
groups NO, or SO, H first enter the side-chain and then pass into 
the nucleus by intramolecular migration. Although a great many 
compounds are now already known containing groups linked to N 
or O which, under the influence of certain agencies, shift towards 
the nucleus, it was in these cases up to the present not proved with 
absolute certainty that we are really dealing here with a rearrangement 
of atoms or groups in a molecule and not with a reaction in which 
several molecules take part, which according to some authors is not 
improbable *). In order to investigate this it became necessary to 
know the velocity of reaction. If the reaction took place mono- 
molecularly, we should be really dealing with an intramolecular 
displacement; a bimolecular reaction would point to a double decom- 
position between two molecules. 
As a suitable example for this research, Prof. Losry pr Bruyn 
pointed out to me the conversion of acetylehloroanilide into para- 
chloroacetanilide under the influence of hydrochlorie acid, first 
discovered by Brnpmr *) 
EEN ns, 
CH, CO NC JH — CH, CO NC fol. 
RD 4 
It is known that the chlorine in acetylehloroanilide may be determ- 
ined by adding potassiumiodide to its acetie acid solution and titra- 
ting the liberated iodine; p-chloroacetanilide does not react with K I: 
C, H, NCICOCH, +2 HI=C, H‚ NH CO CH, 4 HC +1, 
The acetylehloroanilide was prepared according to the directions of 
Carraway and Orron ®) by shaking acetanilide with a solution of 
bleaching powder containing potassium bicarbonate. Within half a 
minute to a minute it will be noticed that the acetanilide has nearly 
entirely dissolved; after a few minutes the acetylchloroanilide sepa- 
rates in a crystalline state. CHarrawar and Orton state that this 
1) Proce. 25 Jan. and 29 March 1902. 
2) Armstrone, Journ. Chem. Soc. 77. 1053. 
3) Ber. 19. 2273. Srossen, Ber. 28. 3265. 
4) Journ. Chem. Soc. 79. 278. 
