A Manual of the Chemistry of the Carbon Compounds

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THE CARBON COMPOUNDS, 339 solutions. It forms large colourless crystals, resembling alum; it melts at 64°, and boils at 236°, DibromopJmd C6H4-| Q^ is produced by the further action of bromine, and forms glistening, white crystals, melting at 40°, and subliming even at the common temperature. Tribromophenol C6Ha -J Q& is obtained as a crystalline precipitate by adding bromine water to an' aqueous solution of phenol. It is quite insoluble in water, and this reaction may be used for the quantitative determination of phenol, as well as for detecting small quantities of it—for example, in urine, or in drinking water from wells situated near gas-works, &c. Aniline and some other bodies give similar precipitates with bromine water; but that produced by phenol differs from these by beingeaaily reduced to phenol, which can be recognized by its characteristic smell This reduction is readily effected by treating tribromophenol with dilute sulphurio acid and sodium amalgam, Telm- and Paticibromojihenol are also known; both are crystalline solids. Moniodoplwnol CaH4-| «„ exists in three isomeric modifications. The two of these are formed together by acting with iodine and iodic acid on an alkaline solution of phenol:— 5CflH6.OH + 2I2 + HIO3 = 5C6H4I.OH + 3H2O (Ww-wdop/ienoJ is also obtained pure by boiling diazo-iodobenzene sulphate with water. It forms flat, glistening needles, possessing a faint but disagreeable smell; nitric acid decomposes it with the separation of iodine. Metadodophcnol is an oily liquid, but has not yet been obtained perfectly pure. Paraiodophenol has been prepared from the dlazo-iodobenzeiw sulphate obtained from para-iodaniline. It crystallizes in needles, aud yields, with fuming nitric acid, substitution-products, without iodiue being liberated. The same compound is also formed, together with a small quantity of its isonusrides, by acting with iodine on phenol in the presence of mercuric oxide:— 2CaHt.OH + 2I? + HgO - 2C0H4I.OH + HgI2+ H2O DIOXYBENZEKE8. The three isomeric dioxybenzenes have been prepared by fusing the iodophenols with caustic potash :— 7, 2
340 THE 0BBMI8TRY OF Hydroquinone is prepared by heating ortho-iodophenol with potash to 180°. This body was first obtained by suspending quinone C6H.O2 (see below) in water, and passing sulphur dioxide into it until a colourless solution is formed:— C A { o> + 2H *° + S0 * = C « H * { OH + S0 * H * Hydroquinone crystallizes in rhombic prisms, melting at 172°, and subliming with partial decomposition at a higher temperature. It exists as glucoside, called arhdm, in the leaves of the bearberry (Arbutus Urn uni) and other Ericaceae; when arbutin is boiled with dilute sulphuric acid, it is resolved into hydroquinone and dextrose ;— o C6HUO5 + 2 } ° - C « H * {OH + W ^ Hydroquinone does not yield substitution-products with bromine and chlorine, because these elements oxidize it first to quinone. But substituted hydroquinones are readily formed by the action of sulphur dioxide and water on chloro- and bromo-quinones, DinUrohydroquinone C6H2 j /jig ? •—^ v tne a^ion of concentrated nitric acid on arbutin, dinitroarbutin is formed, which, on boiling with very dilute sulphuric acid, is resolved into dextrose, and dinitrohydroquinone. It crystallizes in golden-yellow plates, dissolving with a blue colour in alkalis, Quinone C6H44 Q>.—This compound was first obtained by oxidizing quinic acid C6H7(OH)4COgH with manganese dioxide and sulphuric acid; and it is also formed by the oxidation of hydroquinone and several other derivatives of benzene. Quinone is a very volatile body, subliming readily in brilliant golden-yellow needles, possessing a suffocating smell, like iodine, It is but slightly soluble in cold water, more freely in boiling water and alcohol and ether; the solution has a yellow colour, and produces brown stains on the skin, ( O OP IT OTT Quinkydrone, or green, Hydroquinone C0H4 •! o OcV OH' * s f° rme( * by the incomplete reduction of quinone with sulphurous acid, and by the direct combination of quinone and hydroquinone. It is also produced by adding chlorine-water gradually to a solution of hydroquinone :— f OH HO.C0H,.0H 2rl _ r H ( O.OC0H4.OH „ , 4 { OE + HO.cX-OH + J01 * t(lH + 4HC1 « 10.OCX-OH Quinhydrone crystallizes in smooth, long needles, possessing a splendid beetle green lustre, and a faint smell of quinone, and dis-
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A MANUAL OF THE T H E C A R B O N C
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PREFACE. THE arrangement adopted in
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vfii C0NTENT9. PARAFFINSOB HYDROCAR
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x CONTENTS. FAI1B TKRPENES AND CAMP
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xii C0STJBNT8. PAGE COMPOUNDS CONTA
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8 THE CHEMISTBY OF both how to deco
Page 13 and 14:
THE CHEMISTRY OF Eaoh molecule of t
Page 15 and 16:
THE CHEMISTRY OF /Xi. Hypophosphoro
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TBB OSEMISTRY OF Series C Him. Seri
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10 THE CHEMISTRY OF two atoms of ch
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12 THE CHEMISTRY OF atoms of hydrog
Page 23 and 24:
14 TBS CBEMIBTMY OF metal ahd methy
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16 THE CHEMISTRY OF point of the tu
Page 27 and 28:
THE CHEMISTRY OF burned with fused
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in THE CHEMISTRY OF a mixture of ni
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23 TUB CHEMI8THY OF To find the vol
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THE CHEMISTRY OF The apparatus (Fig
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26 THE CHEMISTRY OF ignition 64*67
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28 THE CEKM.WTRY OF One molecule of
Page 39 and 40:
30 THE CHEMISTRY OF acetic add bein
Page 41 and 42:
32 THE CHEMISTRY OP Ohlomcotic AoM.
Page 43 and 44:
34 Normal. CH3 CH2 CH8.OH Propional
Page 45 and 46:
36 THE CHEMISTRY OF By comparing tl
Page 47 and 48:
38 TUB CHEM1STBY OF In the series o
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40 THE CHEMI8TRY OF Boiling-point.
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42 THE CHEMISTJ17 OF Acetic Acid Ct
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U THE CHEMISTRY OF exist in two mod
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46 TEE CHEMISTRY OP In the flask re
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48 THE CHEMISTRY OF CYANOGEN COMPOU
Page 59 and 60:
50 TEE CHEMISTRY OF By the inverse
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52 THE CEEMI8TRY OF The commeroial
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M THE CHEMISTRY OF animal matter. B
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56 TEE CHEMISTRY OF formed and a fe
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aft THE GHEU1STRY OP ifi water; thi
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00 THE CHEMISTRY OF cyanate with di
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62 TOM OMBMISTRY OF heated in seale
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64 THE CHEMISTRY OF refreshing tast
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66 THE CHEMISTRY OF consisting of p
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68 THE CHEMISTRY OF with a concentr
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70 TUB WBfflSTRY OF a salt wbiob is
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72 THE OUBMIStHY OF have been oalle
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74 THE CHEMISTRY OF among the paraf
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70 THE CHEMISTRY OF been known long
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78 THE CHEMISTRY OF Tetrethylammoii
Page 89 and 90:
80 THE CHEMISTRY OF ethylamine and
Page 91 and 92:
82 THE CHEMISTRY OF -S Etbyl Thiace
Page 93 and 94:
84 THM CHEMISTRY OF CH8 CH8t CH, CO
Page 95 and 96:
86 TEE OHEMTSTRY OF (2) SECONDARY A
Page 97 and 98:
88 THE CHEMISTRY OF acid and dimeth
Page 99 and 100:
80 THE CHEMISTRY OP CH8 CH, CH8 + N
Page 101 and 102:
92 THE CHEMISTRY OF ~ 21°. It burn
Page 103 and 104:
04 TEE CHEMISTRY OF Methyl CarbhnUe
Page 105 and 106:
08 THE CHEMISTRY OF It is a colourl
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08 THE CHEMISTRY OF These componnds
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100 THE CHBMIXTRY OF On adding sodi
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102 TEE CHEMI8THY OF in sealed tube
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104 THE CHEMISTRY OF red-hot platin
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106 THE CHEMISTRY OF rhombic (CHO2)
Page 117 and 118:
108 THE CHEMI8THY OF —100° it be
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lto TBS CUMMISTRY OP strong alcohol
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112 THE CHEMISTRY OF Diethylated et
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114 THE CHEMISTRY OF tained by pass
Page 125 and 126:
116 THE CHEMISTRY OF duced by the a
Page 127 and 128:
18 THE CHEMISTRY OF Ethyl Xanthate
Page 129 and 130:
130 THE CHEMISTRY OF colourless liq
Page 131 and 132:
122 THE CHEMISTRY OF was discovered
Page 133 and 134:
124 THE CHEMISTRY OJP set free by m
Page 135 and 136:
186 THE CHEMISTRY OF oily liquid, b
Page 137 and 138:
128 THE CHEMISTRY OF mercaptan, thi
Page 139 and 140:
130 THE CHEMISTRY OF fire in the ai
Page 141 and 142:
132 THE CHEMISTRY OF Pb2Cl4 + 2Zn(C
Page 143 and 144:
134 TBS CBJSMI8TRY OF trated sulphu
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130 THE CHEMISTRY OF C»H4O.CNH, wh
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133 TBE CHEMISTRY OF By dissolving
Page 149 and 150:
140 THE CHEMISTRY OF at 187°, and
Page 151 and 152:
142 THE CHEMISTRY OF If silicon tet
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144 THE CHEMI8TMY OF In a similar m
Page 155 and 156:
146 TEE CHEMISTRY OF Chloral or Tri
Page 157 and 158:
148 THE CHEMI8TRY OF SUBSTITUTION-P
Page 159 and 160:
160 THE CHEMISTRY OF EROm-GROUP. Pr
Page 161 and 162:
162 THE CHEMISTRY OF (1) CH,, CH, C
Page 163 and 164:
164 TBE 0HEMI8TRY OF BUTYL-GEOOP. T
Page 165 and 166:
166 THE CHEMISTRY OF Q*jr o* f G* +
Page 167 and 168:
168 TEE CHEMISTRY OF The same cryst
Page 169 and 170:
180 THE OHEMI8TRY OF described prim
Page 171 and 172:
162 THE GBEM18TRY OF salt, one volu
Page 173 and 174:
164 TEE CHEMISTRY Off- CH8 CH8 CH-C
Page 175 and 176:
166 J'flE CHEMISTRY OF C H ) acetat
Page 177 and 178:
168 THE CHEMISTRY OF HEPTYL GROUP.
Page 179 and 180:
170 THE OBEMI8TRY OF of ocfcylic ac
Page 181 and 182:
172 TEE CHEMISTRY OF £CUH3^S1]' is
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174 THE CHEMISTRY OP needles or lam
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176 THE CBEM8TRY OF Olefines may al
Page 187 and 188:
178 TME CHEMISTRY OF ncids, forming
Page 189 and 190:
180 THE OSEMI8TRY OF They ore also
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182 THE OHEMISTBY OF By employing t
Page 193 and 194:
184 THE CHBMHTRY OF CO.OH CO.OH CH2
Page 195 and 196:
186 THE CHEMISTRY OF From this tabl
Page 197 and 198:
188 THE CHEMT8TKY OF horns pentachl
Page 199 and 200:
100 THE CHEMISTRY OF Monoxotliylnni
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192 THE CUEMISUBT OF crystallizes o
Page 203 and 204:
194 THE CHEMISTRY OP with silver ox
Page 205 and 206:
196 THE CHEMISTRY OF When aldehyde
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198 TEE GKEMISTRY OJf CHg.OCjjHgO M
Page 209 and 210:
200 THE CHEMI8TEY OF It is obtained
Page 211 and 212:
208 THE GBEMISTHY OP water; in ibis
Page 213 and 214:
204 THE CHEMISTRY OF Phosphorus oxy
Page 215 and 216:
206 THE CHEMISTRY OF water and silv
Page 217 and 218:
203 TEE CHEMISTRY OF UH2Br Trimethe
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210 THE OBEM18TRY OF + 3HJJO is pre
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212 TRB CHEMISTRY OF This etherific
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2U THB CHEMISTRY OF Ethene-lactic a
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216 THE CHEMISTRY OF 0H8 CH8 (1) CE
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218 THE CHEMISTRY OF Oxy-isobutyric
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220 THE CHEMISTRY OF the boiling-po
Page 231 and 232:
222 THE CBEM18TBY OF OF SUCCINIC AC
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224 THE CHEMISTRY OF (C4H6O6)8Ca +
Page 235 and 236:
220 THE OJlJSMiaTBY OF TABTAKIC ACI
Page 237 and 238:
TEE CHEMT8TRY OF solution decompose
Page 239 and 240:
830 THE CUBMT8TRY OF ganic substanc
Page 241 and 242:
THE CHEMISTRY OF or butatanine (^^(
Page 243 and 244:
234 THE CHEMISTRY OF ffeptene or Hc
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236 THE 0HEMI8TRY OF It crystallize
Page 247 and 248:
238 THE CHEMISTRY OF Silver Citrate
Page 249 and 250:
240 TBE CHEMIUTKY OF MmMbromopyrota
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242 THE CHEMISTRY OF TJBATBS, Uric
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244 THE CHEMISTRY OF Mesoxalic acid
Page 255 and 256:
246 TBB CHEMISTRY OF ammonium hydur
Page 257 and 258:
248 THE CEEMISTBY OF CH.gNH) EydaiU
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20l> THE CHEMISTRY OF CHEATING AND
Page 261 and 262:
263 THE CEEMI8TRY OF also in the ko
Page 263 and 264:
254 THE CHEMISTRY OF Glycerin was f
Page 265 and 266:
258 THE CHEMISTRY OF produced by th
Page 267 and 268:
258 TEE CHEMISTRY OF Monofai'min C8
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260 THE CHEMISTRY OF into /S chloro
Page 271 and 272:
268 THE 0HEMI8TRY OF Dibroniopropyl
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264 THE CHEMIUTRY OF black mustard
Page 275 and 276:
26B THE CHEMISTRY OF as always thos
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288 THE CHEMISTRY OF The same acid
Page 279 and 280:
270 THE CMEMISTHY OF Mtthglcrotonk
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272 THE CHEMISTRY OF Stearoxylic Ac
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274 THE CHEMISTRY OF Hcxone Dibromi
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£!» THE CHUMiaTRY OF Alii/hue or
Page 287 and 288:
278 THE GSEUISTRY OF Erythrite form
Page 289 and 290:
280 TEE CHEMISTRY OF Isodulcite CgH
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TU&' GHEMISTRY OF PYROM0CIC ALDEHYD
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284 THE CHEMI8TBY OF prisms contain
Page 295 and 296:
286 THE CHEMISTRY OF sugar containe
Page 297 and 298: 2«8 TEE CHEMISTRY OF MELITOSK CBHM
Page 299 and 300: 890 THE OEEMISTRY OF Dextrose forms
Page 301 and 302: 293 2BJ? QHEMI8TR7 OF 0A.LACT08E Is
Page 303 and 304: 894 TBE 0BEMI8TRY OF DEXTRIN. This
Page 305 and 306: 298 THE CUBMISTBY OF fresh acid mix
Page 307 and 308: 888 THE CHEMISTRY OF A small quanti
Page 309 and 310: 300 THE CHEMISTRY OF Terpinol O^SJO
Page 311 and 312: 302 THE OHEMI8T&Y OF to the right,
Page 313 and 314: 304 1HM CHEMISTRY OF Hydrochloric a
Page 315 and 316: 306 TBS 0BEMI8TRY OF OXIDATION-PROD
Page 317 and 318: 308 ISE OHBMISTBY OF with water. By
Page 319 and 320: 310 THE CHEMISTRY OF when acted upo
Page 321 and 322: 312 THE CHEMISTRY OF TOWJENK, METHY
Page 323 and 324: 3U TEE CBEMISTUY OF oxidation a mon
Page 325 and 326: 316 THE CJUEMISTRT OF The first for
Page 327 and 328: 318 TEE CHEMISTRY OF soften, it is
Page 329 and 330: 320 THE GHMMJSTSY OF consists in th
Page 331 and 332: 322 TEE CHEMISTRY OP fying at - 8°
Page 333 and 334: 324 THE CHEMISTRY OF cyanvuic acid
Page 335 and 336: 326 THE GRBMISVBY OF The nitrobenze
Page 337 and 338: 328 THE CHEMISTRY OF produced by th
Page 339 and 340: 330 THE CEEMI8TRY OB benzoic acid t
Page 341 and 342: 332 TEE CHEMISTRY OF Phenol lias be
Page 343 and 344: 334 THJB CHEMISTRY OF Phmyl Sulphid
Page 345 and 346: 336 THE CHEMISTRY OJP water, and cr
Page 347: 338 THE OMBMISTRT OF HALOID SUBSTIT
Page 351 and 352: 342 TEE CHEMISTRY OF •warm potash
Page 353 and 354: 344 THE CHEMISTRY OF oxygen from a
Page 355 and 356: 346 THE CHEMISTRY OF action is over
Page 357 and 358: 348 TEE CHEMISTRY OF More than seve
Page 359 and 360: 360 THE OHEMISTBT OF toluene is for
Page 361 and 362: 352 THE CHEMISTRY OF DIOXVTOLUKKfiS
Page 363 and 364: 364 THE CMSMI8TBY OF BENZYL COMPOUN
Page 365 and 366: 359 THE CHEMISTRY OF f Ttf IT Bmyl-
Page 367 and 368: 3SS THE CHEMISTRY OF In these two l
Page 369 and 370: 360 TBS CHEMISTRY OP (4.) When the
Page 371 and 372: 362 TEE CHEMISTRY OF 2CeH6.CO.OHa +
Page 373 and 374: 364 THE CHEMISTRY OF a Dichlorobenz
Page 375 and 376: 368 TEE CHEMISTRY OF out in colourl
Page 377 and 378: THE GHEMI8TBY OF ( § ^ } fa formed
Page 379 and 380: 3/0 THE CHEMISTRY OF Phosphorus pen
Page 381 and 382: 372 THE CHEMISTRY OF By acting with
Page 383 and 384: 374 THE CREMI8TBY OF pyrocatechin,
Page 385 and 386: 376 THE CHEMISTRY OF isoxylene, by
Page 387 and 388: 378 THE OBEMISTItY OP Paratoluonitr
Page 389 and 390: 380 THE CHEMISTRY OP filtered solut
Page 391 and 392: 382 THE CHEMISTRY OF When calcium j
Page 393 and 394: 384 TEE CHEMISTRY OF is obtained by
Page 395 and 396: 388 THE CHEMISTRY OF COMPOUNDS WITH
Page 397 and 398: THE CHEMISTRY OF Dibronwpseudocvmen
Page 399 and 400:
300 TRE CHEMISTRY OP Ethytbmzoic Ac
Page 401 and 402:
392 THE CHEMISTRY OF styrolene, and
Page 403 and 404:
391 THE CHEMISTRY Off PHENYL-LAOTIO
Page 405 and 406:
38ff TBE CHEMISTRY OF base and an a
Page 407 and 408:
THE GBMMISTRY 09 VeraMc Add CgHjCOE
Page 409 and 410:
4 THE CHBMIHTRY OF from oil of turp
Page 411 and 412:
402 THE CHEMISTRY Of of hydrogen in
Page 413 and 414:
404 TEE CHEMISTRY OP Mellitic acid
Page 415 and 416:
406 THE OEBMI3TBY OF water is conve
Page 417 and 418:
408 TSB OHEMISTMT OF powder, which
Page 419 and 420:
410 TEE CHEMISTRY OF scale by heati
Page 421 and 422:
412 THE CHBMI8THY OF Pare aurin is
Page 423 and 424:
414 THE CHEMISTRY OF JSixin CjjHjaO
Page 425 and 426:
416 THE CHEMISTRY OF Carbazol cryst
Page 427 and 428:
418 TEE OEEMISTBT OF is formed by t
Page 429 and 430:
420 THE CHEMISTRY OF chloride'over
Page 431 and 432:
422 THE CHEMISTRY OF It crystallize
Page 433 and 434:
424 THE CHEMI8TBY OF above 300°, a
Page 435 and 436:
426 THE CRHMI8TRY OF soluble in wat
Page 437 and 438:
428 THE CHEMISTRY OF TrioxinSd or I
Page 439 and 440:
430 THE CHEMISTRY OF Naphthalene, t
Page 441 and 442:
432 THE CHEMISTRY Off SUBSTITUTED N
Page 443 and 444:
434 THIS CHEMISTRY OF fluorescence.
Page 445 and 446:
436 THE CHEMISTRY OF trioxide in th
Page 447 and 448:
43S TUB CHEMISTRY OF also been prod
Page 449 and 450:
*W THE OHUMISTBY 01> a Dinaphthyl K
Page 451 and 452:
442 TBB OHEMIHTBY Of acids. It crys
Page 453 and 454:
444 THE CHEMISTRY OF HYDE0-ANTHBACE
Page 455 and 456:
448 THE GBBMISTKY OF 273°, and sub
Page 457 and 458:
4tS THE CHEMISTRY OF OXYANTHBAQUINO
Page 459 and 460:
450 THE GHEMISTltY OF precipitated
Page 461 and 462:
482 TRE CHEMISTRY OF with a crimson
Page 463 and 464:
454 THE CHEMISTRY OF A 0 - 2H2 Dime
Page 465 and 466:
488 THE CHEMISTRY OF RETENE vjjii,,
Page 467 and 468:
•153 TBS CHEMISTRY OF Crude coal-
Page 469 and 470:
460 THE CMEMI8TRY OF ferment of bit
Page 471 and 472:
462 THE CHEMISTRY OF sugars, which
Page 473 and 474:
464 TUB CHEMISTRY OP gallic acid or
Page 475 and 476:
TEE CBBMI8TRY OF sweetish astringen
Page 477 and 478:
468 THE 0REMI8TRY OF It forms a sul
Page 479 and 480:
470 THE CHEMISTRY OF NATURAL BASES
Page 481 and 482:
478 THE CHEMISTKY OF the cold, but
Page 483 and 484:
474 TBE CHEMISTRY OF speedy vomitin
Page 485 and 486:
470 THE CHEMI8TKY OJ" Gryptopine C^
Page 487 and 488:
478 TEB CE£MISTRY OF The most impo
Page 489 and 490:
480 THE OHEiliaTBY OF little sulphu
Page 491 and 492:
482 THE VHBMISTRY OF Piperonaldehyd
Page 493 and 494:
484 THE OUEMISTKY OF when impure po
Page 495 and 496:
486 THE CHEMI8TBY OF definite compo
Page 497 and 498:
THE OJIEMISTMY OF COMPOUNDS CONTAIN
Page 499 and 500:
490 TME CHEMISTBT OF dissolving in
Page 501 and 502:
402' TBE OftEMISTMY Off aspartic ac
Page 503 and 504:
494 THE CHEMISTRY OF Htemaglobin co
Page 505 and 506:
490 THE CHEMISTRY OF with water. Th
Page 507 and 508:
498 THE CHHMI8TBY OF THE CARBON COM
Page 509 and 510:
600 INDEX. Acid, oltramonoobloropyr
Page 511 and 512:
602 Aoid, sulphocarbonio, 68 Aosoul
Page 513 and 514:
m INDEX. Cuein vegetable. 4P2 Cellu
Page 515 and 516:
506 Ethine-naphthabne, 48S Ethinyl-
Page 517 and 518:
608 LeYobom&ol, 808 Levulosan, 291
Page 519 and 520:
610 INDEX. Perchloretbyl osido, 112
Page 521:
612 INDEX. Tribromacetyl-urea, 217
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A Manual of the Chemistry of the Carbon Compounds

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