Dr. R. Hoffmann on Monochloracetic Acid. 57 
amalgam, just as Kolbe and Melsens found to be the case with 
trichloracetic acid. With a view of obtaining a corresponding 
bromine compound, Hoffmann sealed up bromine with acetic 
acid in a glass tube ; but although they were exposed at a tem- 
perature of 100° C. to the strongest summer sunlight, no action 
was observed. 
Chloral, Ct HCI, 02, is generally considered to be a substitu- 
tion product of aldehyde, C* H*, O*, in which three equivalents of 
hydrogen are replaced by three of chlorine. Wurtz* wished to 
ascertain if chloral were really formed by the direct action of 
chlorine upon aldehyde, and exposed anhydrous aldehyde in ex- 
cess to the action of chlorine. The only substitution product 
he obtained was chloride of acetyle, C+ H® ClO?, while at the 
same time a quantity of aldehyde was changed into metaldehyde, 
C8 H8 04, the modification into which it passes on being long 
kept, and some of this had been changed to a substance, 
C* H7 C104, by the action of chlorine. 
He further tried whether chloride of acetyle gives chloral by 
the continued action of chlorine, and with this view placed chloride 
of acetyle, C1 H? 0? Cl, in large globes filled with chlorine, and 
exposed them to the action of sunlight. A liquid was obtamed, 
which gave on fractional distillation a substance boiling between 
100° and 105° C., which was monochlorinated chloride of acetyle, 
C4H2C1202. It is a colourless liquid, having an extremely 
irritating odour. The action of water on this substance gives 
rise to the formation of monochloracetic acid ; thus 
C4 H? Cl? 0? + 2HO= HCl + C* H® Cl0* 
Monochlorinated Monochloracetic 
chloride of acetyle. acid. 
The reactions of ammonia and of alcohol upon monochlorinated 
chloride of acetyle, have been examined by Willm. On mixing 
alcohol with this substance a very violent action ensues, and the 
vessel in which it takes place requires to be cooled down. On 
washing the product with water, and rectification, a colourless 
liquid of etherial odour, and boiling at 1435, is obtained. This 
is monochloracetate of zthyle, and its formation is thus ex- 
pressed :— 
C4 H6 024 C4 H2 Cl? 02, Cl= HC1+ C4 H? O, C* H? C1O®. 
Alcohol. | Monochlorinated Monochloracetate 
chloride of acetyle. of ethyle. 
It is therefore acetic acid in which one equivalent of hydrogen in 
the acid is replaced by chlorine, for by acting upon it with caustic 
potash it is changed into monochloracetate of potash and alcohol. 
Monochloracetamide, C4H?C1 02, N H?, is obtained by the action 
* Annales de Chimie et de Physique, January 1857. Liebig’s Annalen, 
April 1857. 
