A Manual of the Chemistry of the Carbon Compounds

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TEE CARBON COMPOUNDS. 169 secondary heptyl alcohol; it boils at 132° and yields on further oxidation acetic acid and pentylic acid. Isokeptyl Aleolwl (CH3)2C5Hg.OH has been obtained, together with /ITT \ m e t h y l - a m y l c a r b i n o l , Q J J \ Q J J 8 f C H . O H , f r o m e t h y l - a m y L T h e p r i m a r y alcohol b o i l s at 1 6 5 , a n d y i e l d s o n o x i d a t i o n isoheptylio a d d ( C H A C A . C O j j H , a n o i l y l i q u i d b o i l i n g at 2 1 2 ° . T h e s e c o n d a r y a l c o h o l b o i l s a t 1 4 6 ° . C H ) M e t h y l - a m y l K e t o n e / n u x n r r s \ C O is a l i m p i d l i q u i d b o i l i n g a t 1 4 4 ° , w h i c h h a s b e e n p r o d u c e d b y t h e a c t i o n o f z i n c - m e t h y l o n i s o - c a p r o y l chloride, a s w e l l a s t h a t o f z i n c - a m y l o n a c e t y l c h l o r i d e , a n d is a l s o f o r m e d b y o x i d i z i n g m e t h y l - a m y l c a r b i n o L T r i e t h y l C a r b i n o l C ( C 8 H 6 ) S O H . — T h i s t e r t i a r y h e p t y l a l c o h o l is p r o d u c e d b y t h e a c t i o n o f z i n c - e t h y l o n p r o p i o n y l c h l o r i d e . I t is a c o l o u r l e s s l i q u i d , b o i l i n g at 1 4 2 ° a n d s m e l l i n g l i k e c a m p h o r . C h r o m i c a c i d s o l u t i o n o x i d i z e s it to m e t h y l - d i e t h y l - e t h m e ( C g l L ^ C = C . C H j , w h i c h b y f u r t h e r o x i d a t i o n is r e s o l v e d i n t o a c e t i c a c i d a n d p r o p i o n i o acid. O C T Y t , G R O U P . N o r m a l Octyl A l e o h o l C < f l g 1 0 . — T h e e s s e n t i a l oil o f t h e s e e d s o f c o w ' s p a r s n i p ( B e r a c k u m tfpondylium) c o n t a i n s a large q u a n t i t y o f o c t y l a c e t a t e a n d s o m e o c t y l c a p r o a t e , a n d t h e oil o f t h e c o m m o n p a r a n i p consists c h i e f l y o f o c t y l b u t y i a t e . T h e a c e t a t e is a m o b i l e liquid, s m e l l i n g l i k e o r a n g e s a n d b o i l i n g a t 2 0 7 ° . O n h e a t i n g t h e s e e t h e r s w i t h a n a l c o h o l i c s o l u t i o n o f c a u s t i c p o t a s h , o c t y l a l c o h o l is o b t a i n e d , a c o l o u r l e s s l i q u i d , i n s o l u b l e i n w a t e r , b o i l i n g a t 1 9 5 ° , a n d p o s s e s s i n g a s t r o n g a r o m a t i c s m e l l . O n s a t u r a t i n g it w i t h h y d r o - c h l o r i c a c i d g a s a n d h e a t i n g t h e m i x t u r e , octyl c h l o r i d e C 8 H 1 7 C 1 is f o r m e d , a l i q u i d b o i l i n g a t 1 8 0 ° , a n d p o s s e s s i n g a f a i n t o d o u r . Q d y l i o d i d e C g H 1 7 I b o i l s at 2 2 1 ° ; it is o b t a i n e d b y a d d i n g i o d i n e g r a d u a l l y t o a m i x t u r e o f t h e a l c o h o l w i t h a m o r p h o u s p h o s p h o r u s , a n d distilling. B y a c t i n g o n t h e i o d i d e w i t h z i n c a n d h y d r o c h l o r i c a c i d , o c t a n e C S H 1 ? is f o r m e d ; it is a l s o o b t a i n e d b y t h e a c t i o n o f s o d i u m u p o n b u t y l iodide, a n d o c c u r s i n A m e r i c a n p e t r o l e u m . I t b o i l s a t 1 2 4 ° . B y t r e a t i n g t h e a l c o h o l w i t h a s o l u t i o n o f p o t a s s i u m d i c h r o m a t e i n d i l u t e s u l p h u r i c acid, octylic a c i d C 8 H 1 B 0 2 is f o r m e d , a c r y s t a l l i n e m a s s , m e l t i n g a t 1 7 ° a n d b o i l i n g at 2 3 3 ° . I t h a s a s h a r p r a n c i d taste a n d a f a i n t s m e l l , w h i c h o n h e a t i n g b e c o m e s p u n g e n t a n d sudorific. A n a c i d h a v i n g t h e s a m e c o m p o s i t i o n a n d g r e a t r e s e m - b l a n c e t o n o n y l i c a c i d is c a p r y l i c a d d , w h i c h o c c u r s i n b u t t e r a n d o t h e r fats ; it m e l t s a t 14", a n d boils b e t w e e n 2 3 6 ° a n d 2 4 0 ° . E t h y l o c t y l a t e ^ h > 0 is f o r m e d b y a d d i n g s u l p h u r i c a c i d t o a s o l u t i o n
170 THE OBEMI8TRY OF of ocfcylic acid in ethyl alcohol; it boils at 205° and smells like pineapples. Ethyl capryMe is a similar liquid, boiling at 214°. Secondary Octyl Alcohol or Mcihyl-liexyl Carbinol ^7? \ CH.OH, 0 13 J formerly called capryl alcohol, is produced by distilling castor-oil soap with caustic soda. Castor-oil contains ricinoleio acid,-which by alkalis is decomposed into the alcohol and sebacic acid:— QiAfO, + 2NaOH = C8H18O + C10H10Na2O, + H, The distillate contains besides the secondary alcohol other products ; it ia repeatedly rectified over caustic soda and then subjected to fractional distillation. Methyl-hexyl carbinol is a colourless oily liquid, possessing an aromatic smell, and boiling at 181°. By a dilute solution of chromic acid it is oxidized to methyl-hexyl ketone f CO, a liquid boiling at 171°. This ketone is sometimes formed as a by-produot in the preparation of the alcohol. Secondary octyl chloride CoH,.Cl "smells like oranges and boils at 173°. The iodide boils at 212 , and yields by the action of nascent hydrogen normal octane. NONYL GROUP. This group has been so far very little studied. Felargonic acid, O8H18O2 occurs in the essential oil of Pelargonium roseum, and is also formed by oxidizing methyl-nonyl ketone, the chief constituent of oil of rua This acid has a faint, rancid odour ; it melts at 18° and boils at 250°. Notiylio Acid ^iy^ IO.—This acid, which has great resemblance to pelargonic acid, has been prepared by heating octyl iodide with potassium cyanide and decomposing the nitrile thus formed with caustic potash. It fuses at 12" and boils at 254'. DEOATYL OROtJP. Diamyl, or Tetramethyl Hemne CgHL^CHj). is obtained by decomposing amyl iodide with sodium; it is a colourless mobile liquid, boiling at 158°. On acting on it with chlorine decatyl chloride is formed, which, when heated with potassium acetate and acetic acid, yields the acetate, a liquid possessing a pleasant smell like oranges. On decomposing it with an alkali, decatyl alcohol 10 jJ [ 0 is obtained, an oily liquid boiling at about 210°—215°, and smelling like
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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
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THE CHEMISTRY OF Eaoh molecule of t
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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
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14 TBS CBEMIBTMY OF metal ahd methy
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16 THE CHEMISTRY OF point of the tu
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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
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30 THE CHEMISTRY OF acetic add bein
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32 THE CHEMISTRY OP Ohlomcotic AoM.
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34 Normal. CH3 CH2 CH8.OH Propional
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36 THE CHEMISTRY OF By comparing tl
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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
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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
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80 THE CHEMISTRY OF ethylamine and
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82 THE CHEMISTRY OF -S Etbyl Thiace
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84 THM CHEMISTRY OF CH8 CH8t CH, CO
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86 TEE OHEMTSTRY OF (2) SECONDARY A
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88 THE CHEMISTRY OF acid and dimeth
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80 THE CHEMISTRY OP CH8 CH, CH8 + N
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92 THE CHEMISTRY OF ~ 21°. It burn
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04 TEE CHEMISTRY OF Methyl CarbhnUe
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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)
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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
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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
Page 145 and 146: 130 THE CHEMISTRY OF C»H4O.CNH, wh
Page 147 and 148: 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
Page 153 and 154: 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: 168 THE CHEMISTRY OF HEPTYL GROUP.
Page 181 and 182: 172 TEE CHEMISTRY OF £CUH3^S1]' is
Page 183 and 184: 174 THE CHEMISTRY OP needles or lam
Page 185 and 186: 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
Page 191 and 192: 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
Page 201 and 202: 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
Page 207 and 208: 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
Page 219 and 220: 210 THE OBEM18TRY OF + 3HJJO is pre
Page 221 and 222: 212 TRB CHEMISTRY OF This etherific
Page 223 and 224: 2U THB CHEMISTRY OF Ethene-lactic a
Page 225 and 226: 216 THE CHEMISTRY OF 0H8 CH8 (1) CE
Page 227 and 228: 218 THE CHEMISTRY OF Oxy-isobutyric
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220 THE CHEMISTRY OF the boiling-po
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222 THE CBEM18TBY OF OF SUCCINIC AC
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224 THE CHEMISTRY OF (C4H6O6)8Ca +
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220 THE OJlJSMiaTBY OF TABTAKIC ACI
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TEE CHEMT8TRY OF solution decompose
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830 THE CUBMT8TRY OF ganic substanc
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THE CHEMISTRY OF or butatanine (^^(
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234 THE CHEMISTRY OF ffeptene or Hc
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236 THE 0HEMI8TRY OF It crystallize
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238 THE CHEMISTRY OF Silver Citrate
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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
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246 TBB CHEMISTRY OF ammonium hydur
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248 THE CEEMISTBY OF CH.gNH) EydaiU
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20l> THE CHEMISTRY OF CHEATING AND
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263 THE CEEMI8TRY OF also in the ko
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254 THE CHEMISTRY OF Glycerin was f
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258 THE CHEMISTRY OF produced by th
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258 TEE CHEMISTRY OF Monofai'min C8
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260 THE CHEMISTRY OF into /S chloro
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268 THE 0HEMI8TRY OF Dibroniopropyl
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264 THE CHEMIUTRY OF black mustard
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26B THE CHEMISTRY OF as always thos
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288 THE CHEMISTRY OF The same acid
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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
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278 THE GSEUISTRY OF Erythrite form
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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
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286 THE CHEMISTRY OF sugar containe
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2«8 TEE CHEMISTRY OF MELITOSK CBHM
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890 THE OEEMISTRY OF Dextrose forms
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293 2BJ? QHEMI8TR7 OF 0A.LACT08E Is
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894 TBE 0BEMI8TRY OF DEXTRIN. This
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298 THE CUBMISTBY OF fresh acid mix
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888 THE CHEMISTRY OF A small quanti
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300 THE CHEMISTRY OF Terpinol O^SJO
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302 THE OHEMI8T&Y OF to the right,
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304 1HM CHEMISTRY OF Hydrochloric a
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306 TBS 0BEMI8TRY OF OXIDATION-PROD
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308 ISE OHBMISTBY OF with water. By
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310 THE CHEMISTRY OF when acted upo
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312 THE CHEMISTRY OF TOWJENK, METHY
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3U TEE CBEMISTUY OF oxidation a mon
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316 THE CJUEMISTRT OF The first for
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318 TEE CHEMISTRY OF soften, it is
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320 THE GHMMJSTSY OF consists in th
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322 TEE CHEMISTRY OP fying at - 8°
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324 THE CHEMISTRY OF cyanvuic acid
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326 THE GRBMISVBY OF The nitrobenze
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328 THE CHEMISTRY OF produced by th
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330 THE CEEMI8TRY OB benzoic acid t
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332 TEE CHEMISTRY OF Phenol lias be
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334 THJB CHEMISTRY OF Phmyl Sulphid
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336 THE CHEMISTRY OJP water, and cr
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338 THE OMBMISTRT OF HALOID SUBSTIT
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340 THE 0BBMI8TRY OF Hydroquinone i
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342 TEE CHEMISTRY OF •warm potash
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344 THE CHEMISTRY OF oxygen from a
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346 THE CHEMISTRY OF action is over
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348 TEE CHEMISTRY OF More than seve
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360 THE OHEMISTBT OF toluene is for
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352 THE CHEMISTRY OF DIOXVTOLUKKfiS
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364 THE CMSMI8TBY OF BENZYL COMPOUN
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359 THE CHEMISTRY OF f Ttf IT Bmyl-
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3SS THE CHEMISTRY OF In these two l
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360 TBS CHEMISTRY OP (4.) When the
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362 TEE CHEMISTRY OF 2CeH6.CO.OHa +
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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
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3/0 THE CHEMISTRY OF Phosphorus pen
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372 THE CHEMISTRY OF By acting with
Page 383 and 384:
374 THE CREMI8TBY OF pyrocatechin,
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376 THE CHEMISTRY OF isoxylene, by
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378 THE OBEMISTItY OP Paratoluonitr
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380 THE CHEMISTRY OP filtered solut
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382 THE CHEMISTRY OF When calcium j
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384 TEE CHEMISTRY OF is obtained by
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388 THE CHEMISTRY OF COMPOUNDS WITH
Page 397 and 398:
THE CHEMISTRY OF Dibronwpseudocvmen
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300 TRE CHEMISTRY OP Ethytbmzoic Ac
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392 THE CHEMISTRY OF styrolene, and
Page 403 and 404:
391 THE CHEMISTRY Off PHENYL-LAOTIO
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38ff TBE CHEMISTRY OF base and an a
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THE GBMMISTRY 09 VeraMc Add CgHjCOE
Page 409 and 410:
4 THE CHBMIHTRY OF from oil of turp
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402 THE CHEMISTRY Of of hydrogen in
Page 413 and 414:
404 TEE CHEMISTRY OP Mellitic acid
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406 THE OEBMI3TBY OF water is conve
Page 417 and 418:
408 TSB OHEMISTMT OF powder, which
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410 TEE CHEMISTRY OF scale by heati
Page 421 and 422:
412 THE CHBMI8THY OF Pare aurin is
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414 THE CHEMISTRY OF JSixin CjjHjaO
Page 425 and 426:
416 THE CHEMISTRY OF Carbazol cryst
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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
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430 THE CHEMISTRY OF Naphthalene, t
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432 THE CHEMISTRY Off SUBSTITUTED N
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434 THIS CHEMISTRY OF fluorescence.
Page 445 and 446:
436 THE CHEMISTRY OF trioxide in th
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43S TUB CHEMISTRY OF also been prod
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*W THE OHUMISTBY 01> a Dinaphthyl K
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442 TBB OHEMIHTBY Of acids. It crys
Page 453 and 454:
444 THE CHEMISTRY OF HYDE0-ANTHBACE
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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
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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
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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^
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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
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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
show all

A Manual of the Chemistry of the Carbon Compounds

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