14 E-J.] 



[l ; L]), iodoform, and acetylene, &c., 

 as under E, below. 



NOTE : Many compounds which can be syn- 

 thesised give carbon tetrabromide on treatment 

 with bromine in the presence of alkali (from 

 acetone [106], Wallach, Ann. 275, 149 ; from 

 Icewtlic acid [50 ; D], acetoacetic acid [Vol. II], 

 dehydracetic acid [75 ; D], &c. Farb. vorm. 

 Meister, Lucius and Briining, Germ. Pat. 76362 

 of 1893 ; Ber. 27, Eef. 930) or with a strong 

 solution of sodium hypobromite (acetone, glycol, 

 glycerol, mannitol, sugars, malic and citric acids, all 

 unsaturated acids, phenol, orcinoJ, the naphthols, 

 anthracene derivatives, &c. Collie, Trans. Ch. Soc. 

 65, 262). 



[F.] Geraniol [36] on heating- with 

 strong- alcoholic potash to 150 gives 

 (with methylheptenone) ethyl alcohol 

 (Tiemann, Ber. 31. 2989). 



[G.] From glycerol [48], alcohol 

 being among the products of the dry 

 distillation of the calcium and sodium 

 derivatives (Destrem, Ann. Chim. [5] 

 27, 20 ; Fernbach, Bull. Soc. [2] 34,, 

 146). 



Or glycerol can be converted into 

 allyl alcohol by distillation with oxalic 

 acid (Tollens, Ann. 156, 129; Tollens 

 and Henninger, Bull. Soc. [2] 9, 394; 

 Briihl, Ann. 200, 174; Linnemann, 

 Ber. 7, 854 ; see also Bigot, Ann. Chim. 

 [6] 22, 464). Allyl alcohol gives ethyl 

 alcohol among the products of decom- 

 position by heating with solid potash 

 (TolJens, Ann. 159, 92) or with phos- 

 phorus pentoxide (Behal, Ann. Chim. 

 [61 16, 360). 



[H.] From aldehyde [92] by reduction 

 with sodium amalgam (Wurtz, Ann. 

 12 3 ; 140). Or indirectly through iodo- 

 form (see under methane [l ; l]) and 

 acetylene as below under I. 



Or from aldehyde through ethylidene 

 chloride by the action of phosphorus 

 pentachloride (Wurtz and Frapolli, 

 Comp. Rend. 47, 418 ; Ann. 108, 223 ; 

 Beilstein, Ann. 113, no; Geuther, Ann. 

 105, 321). Acetylene, ethylene, and 

 ethane are produced by the action of 

 sodium at 200 on ethylidene chloride 

 (Tollens, Ann. 137, 311). 



Or from aldehyde through the oxime 

 whiVV) j nitroethane among the pro- 

 oxidation by permonosulphuric 



,_ ^ ^a,ro's reagent; Bamberger and 



Scheutz, Ber. 34, 2029). From nitro- 

 ethane through ethylamine [Vol. II] 



55 



and then as under FF below. Or the 

 phenylhydrazone of aldehyde gives 

 ethylamine (with aniline) by electrolytic 

 reduction in sulphuric acid (Tafel and 

 Pfeffermann, Ber. 35, 1510). 



NOTE : Ethane is among the products of de- 

 composition of acetaldehyde and propionic alde- 

 hyde [06 ; 2-methylpentanal, A] at a high 

 temperature (Tischtschenko, Ch. Ontr. 1900, 1, 

 586, from Journ. Russ. Soc. 31, 784). 



[I.] From n-propyl alcohol [15] 

 through iodoform (see under methane 

 [l; E]). The latter gives acetylene 

 by the action of certain finely divided 

 metals, such as silver, &c. (see under 

 cymene [6 ; HI]). 



Or iodoform can be converted into 

 methylene iodide by heating with 

 iodine (Hofmann, Ann. 115, 267), with 

 sodium eth oxide in alcohol (Butleroff, 

 Ann. 107, no; 111, 242), by boiling- 

 with strong aqueous hydriodic acid and 

 phosphorus (Lieben, Zeit. 1868, 712; 

 Baeyer, Ber. 5, 1095), or by heating 

 with water and reduced iron (Caze- 

 neuve, Comp. Rend. 98, 369). Methyl- 

 ene iodide on heating with water and 

 copper gives ethylene among other pro- 

 ducts (Butleroff, Ann. 120, 356) ; also 

 on heating with silver powder (Sud- 

 borough, Journ. Soc. Ch. Ind. 16, 408). 



Or from n-propyl alcohol through 

 n-hexane (see under n-hexyl alcohol 

 [23]). Ethylene is among the products 

 formed by passing a mixture of hexane 

 and air over heated platinum (v. Stepski, 

 Monats. 23, 773). Subsequent steps 

 as under A above. 



[J.] From n-Vhtyl alcohol [17] 

 through iodoform (l ; F) and then 

 as above. Or from isobutyl or tertiary 

 butyl alcohol [18; 19] through isobutyl- 

 ene (see under isobutyl alcohol [18 ; A] 

 and under tertiary butyl alcohol [19 ; 

 B]). Ethylene is among the products 

 of pyrogenic decomposition of isobutyl- 

 ene (Noyes ; Beilstein, 1, 115). Ethyl- 

 ene is among- the products formed by 

 passing the vapour of isobutyl alcohol 

 mixed with air over heated platinum 

 (v. Stepski, Monats. 23, 773). 



NOTE : Other generators of isobutylene given 

 under isobutyl and tertiary butyl alcohols are: 

 isoamyl alcohol [22] ; isovaleric acid [Vol. II] ; 

 acetic acid [Vol. II] ; acetone and glycerol [106 ; 

 48]. 



