Chlor ethane

Chlor-ethan- E2, 310, 311. 312, 315 2-Chlor-ethan- -bis-[aziridid] XII/1, 536 2-Chlor-ethan- -bis-[2-chlor-ethylester] XII/1. 443,... 

Chlor-ethan- -(2-chlor-ethylester)-chlorid XIII, 417 E2, 384... 

Chlor-ethan- -diethylester Xll/1, 427, 443 2-Chlor-ethan- -diphenylester XII/1, 147, 151, 426 2-Chlor-ethen- -dialkylester XII/1, 506 2-Chlor-ethen- -dibutylester XII/1, 425 Chlor-ethin- -dialkylester E2, 373 Chlor-cthin- -dimethylester El, 574/ 2-Chlor-2-ethoxy-ethen- -chlorid-ethylester E2,337 2-Chlor-2-ethoxy-ethen- -dichlorid E2,328. 337 4-(2-Chlor-ethyl)-benzol- Xll/1, 368, 377 2-Chlor-l-ethyl-1.3-butadien-l- -dichlorid XII/1,... 

Chlor- -dibutylester XII/2, 814 2-Chlor-ethan- -amid-O-phenylester E2, 465 2-Chlor-ethan- -chlorid-O-ethylester E2, 432 2-Chlor-ethan- -dichlorid XII/1, 554 E2, 432, 463 2-Chlor-ethan- -O-ethylester XII/1, 580, 600 2-Chlor-2-ethylthio-cthan- -dichlorid E2, 432 2-Chlor-2-ethy]thio-ethen- -chlorid-O-ethylester... 

Benzol- -chlorid-ester XII/1, 418 2-Chlor-ethan- -diester E2, 384 (Cl -> OR)... 

CsHl2CIN02Si Nitronsaure 1-Chlor-ethan- -trimethylsilylester EI4h, 948 (R2CH-N02 + RO-SiR3)... 

The next question which arises in regard to ethane is is ethane like methane in being symmetrical, i.e.y are all of the hydrogen atoms alike in their relation to the carbon atoms and to each other The same kind of facts which established this point in regard to methane are also true of ethane, viz., only one mono-chlor ethane is known. We thus conclude that all six hydrogen atoms in ethane are alikey and no matter which one is substituted by chlorine the product is always the same. We may write the structural formula for mono-chlor ethane then ... 

Ethyl chloride, Chlor-ethane, CH3—CH2CI, and ethyl bromide, brom ethane, CH3—CH2Br, are both used as local anesthetics, the latter in dentistry. The former is a gas, boiling as 12.2°, which can be readily condensed to a liquid and is used technically in this form. Ethyl bromide is a chloroform-like liquid boiling at 38.4°. 

Isomerism of Di-chlor Ethanes.—When, however, we study the constitution of the poly-halogen ethanes we find that isomerism occurs just as in the case of the propyl iodides and of the hydrocarbons above propane. In the case of ethane it is a fact that only one mono-substitution product of any type is known, thereby proving the symmetry of the ethane molecule and the like character of all six of the hydrogen atoms. When two hydrogen atoms are substituted by two chlorine atoms two dif event compounds are produced both having the composition C2H4CI2. From the constitution of the ethane molecule, that has been established by its synthesis from methane (p. 16), we can readily see how this may be explained as we may have two hydrogen atoms replaced by two chlorine atoms in two different ways, as follows ... 

Uns3mimetrical Di-chlor Ethane.—These two compounds may also be prepared by other reactions which show us what their true constitution is. When acet-aldehyde, which we have previously proven has the constitution represented by the formula, CH3—CHO, is treated with phosphorus penta-chloride one oxygen atom is replaced by two chlorine atoms and the product is one of the two isomeric di-chlor ethanes. 

This reaction is entirely different from that of phosphorus penta-chloride on alcohol, in which the hydroxyl of the alcohol is replaced by one chlorine, and the mono-halogen substitution product of the hydrocarbon results (p. 81). If our ideas in regard to the constitution of aldehyde are correct, this reaction must mean, that, in the di-chlor ethane formed in this way, the two chlorine atoms are linked to the same carbon atom. Such a structure represents a compound which is plainly unsymmetricaL... 

Symmetrical Di-chlor Ethane.— The isomeric di-chlor ethane is obtained when the unsaturated hydrocarbon ethylene, or ethene takes up two chlorine atoms, forming an addition product. 

According to our ideas in regard to the constitution of the hydrocarbon ethane the only formula for an isomeric di-chlor ethane, differing from the one derived from aldehyde, is one in which the two chlorine atoms instead of being both linked to the same carbon atom are each linked to a diferent carbon atom. This gives us a symmetrical com-... 

Ethylene and Ethylidene Compounds.—The fact that the symmetrical di-chlor ethane is readily prepared from ethylene, has given to it the name of ethylene chloride. To distinguish the two isomers by name the other, the unsymmetrical di-chlor ethane, has been called ethylidene chloride. In connection with our discussion of the constitution of the ethene series of unsaturated hydrocarbons (p. 154), we have used the constitution of ethylene chloride as proving the constitution of ethylene or ethene, as H2C = CH2. Isomerism of the character shown in these two di-chlor ethanes, as above explained, is found in all classes of di-substitution products of ethane, so that we may express the compounds by general formulas as follows ... 

The hexa-halogen ethanes, CX3—CX3, or per-halogen ethanes, are known in both the chlorine and the bromine compounds. Per-chlor ethane, CCI3—CCI3, hexa-chlor ethane is a colorless, crystalline substance with a camphor-like odor and which melts at 184°. Per-brom ethane, CBr3—CBr3, hexa-brom ethane is also a colorless, crystalline substance. 

From Hexa-chlor Ethane.—It may also be prepared by oxidizing a derivative of ethane, viz., hexa-chlor ethane, CCle, with potassium hydroxide. This reaction may be considered as yielding the complete oxidation product of ethane by the replacement of the six chlorine atoms by six hydroxyl groups. This then loses water, as in the case of all compounds which contain more than one hydroxyl group linked to one carbon atom, and di-carboxyl, or oxalic acid results, as follows. 

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