THE UNIFICATION OF REDUCING SUGAR METHODS.(A

to prepare the oxime of the ketone after removal of the thujone by oxida- tion was equally unsuccessful. The authors conclude, therefore, that fenchon...
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PERCY H. WALKER,

202

Derivatives : tribromide, melting point I 2 1-1 2 2 ;l semicarbazone, melting point I 86-1 88' (from methyl alcohol) ; tanacetone keto carbonic melting point 75-76'. The reaction with hydroxylamine gave an oily oxime which crystallized only partially after standing for several months , which fact, together with the observed laevo rotation-a rotation, i t may be noted, slightly higher than any previously recorded-further characterized the substance as cy-thujone. The fraction boiling from roo--103~/40mm. (DZOo, 0.8975; n$O0, 1.4549; [a]LO", - 0 . 6 2 ') was tested for fenchone, since that ketone has been isolated from the oil of thuja occidentalis. Using Wallach's method-oxidation with potassium permanganate, steam distillation, further oxidation with concentrated nitric acid, and recovery of the unaltered fenchone by distillation in steam-only a few drops of oil were obtained which were heavier than water and in which no fenchone was found. An attempt to prepare the oxime of the ketone after removal of the thujone by oxidation was equally unsuccessful. The authors conclude, therefore, that fenchone is not present as stated by BrandeL4 The residue (about 5%) boiling above 110'/40 mm. (DZo0,0.980) was dark brown in color and had a n odor of stewed prunes. This was hydrolyzed with alcoholic potash , steam distilled, and fractionated. A light yellow oil was obtained whose constants show i t to be tanacetyl alcohol (Dz50,0.9266; nLSe,1.46207;[ $29.8;boilingpointat 757 mm., 210-220°), probably present as acetate in the original oil. From the above results, the authors conclude that the volatil oil of thuja plicata is composed of 80-85% thujone, 3-5% pinene, I-2% tanacetyl acetate, I-3% tanacetyl alcohol, leaving about IO% t o be accounted for by loss due to formation of resin during distillation and- experimental losses. DEPARTMENT OF CHBAIISTRY,

UNIVERSITY OF WASHINGTON, SEATTLE.

[CONTRIBUTION FROM

THE CONTRACTSLABORATORY, BUREAUOF STATES DEPARTMENT OF AGRICULTUR%]

CHEMISTRY,UNITED

THE UNIFICATION OF REDUCING SUGAR METHODS. (A CORRECTION.) BY PERCY H. WALKER.

Mr. M. N. Straughn, of the sugar laboratory of this bureau, has recently called attention to certain errors in the tables for lactose given in the Wallach, Anti., 275, 179; 286, 1 0 9 . Wallach, Ibid., 336, 2 5 1 . Wallach, Ibid., 272, 113; 275, 164. Semmler, Bw.,25, 3307. Tiemann and Semmler, Ber., 30, 431. LOC. cit. a

THE UNIFICATION O F REDUCING SUGAR METHODS.

203

article published in THISJOURNAL, 29, 541-554. Table 111, on page 544, giving a comparison of determined and calculated figures on cuprous oxide for definit amounts of sugar, is correct, while Table IV, beginning on page 545 and giving the amounts of sugar for each milligram of cuprous oxide from 10-490, contains errors in the lactose column, the figures disagreeing with the preceding table. These tables were used in compiling the tables given in Bureau of Chemistry, Bull. 107, revised,l pages 243-251, which have been used quite generally for several years, and Mr. Straughn has been the first to call attention to this discrepancy. A careful examination of the original notes showed that there are two misprints in the values given in the Journal for a,b, and c, to be substituted in the equation y = a bx cx2 where y = cuprous oxide and x = reducing sugar, the values of a, b, and c being calculated from the determinations made by the method of least squares as used by Allihn.2 The original article gives the accepted values for lactose as follows: a = 4.1759 b = 1.148697 c =0.00009 The true values which were actually used in making the calculations are : a = 4.1759 b = 1.48697 c = --0.00009 AS before stated, the calculations appearing in Table I11 are correct, but in Table IV errors occur in the figures in columns 3, 4, and 5 , while the figures in columns 6 and 7 are correct. The values in column 4 were calculated from the equation for certain fixed weights of cuprous oxide, and the intermediate values obtained by interpolation, columns 3 and 5 being then derived in a similar manner from column 4. Table I of this article shows a comparison of the values as given in Tables I11 and N of the original article and also the corresponding values taken from the recalculated table. It is impossible to say how the errors occurred, since the sheets on which the calculations were made were destroyed shortly after the article was published. It is obvious, however, that such errors are entirely too great to appear in a table of this character; the figures have, therefore, been recalculated from the original data, and in Table I1 the corrected values for anhydrous lactose (C12H22011), and crystallized lactose3

+

+

The final tables as given in Bureau of Chemistry, Bull. 107, revised, Official and Provisional Methods of Analysis, pp. 243-251, also call for the corrections as shown in Table 11. a J . prpkt. Chem., 22, 46 (1880). a The lactose actually used in determining the values from which these tables are calculated was crystallized lactose of the composition G2Hn0,,l/$H,O.

204

PERCY H. WALKER.

(C12H220,11/2HzO), and crystallized lactose (C,,H,,O,,H,O) are given for each milligram of cuprous oxide from I O to 490. TABLEI.SHOWING MILLIGRAMS OF CUPROUSOXIDE AS DETERMINED, AS ORIGINALLY CALCULATED,AND ---_.__-

.. . . . . . . . . . . . . .

40.. . . . . . . . . . . . . . . 60.

. . . . . . . . . . . .. . *

80 . . . . . . . . . . . .. . . .

. . . . .... 120... . . . . . . . . . . . . . 140.. . . . . . . . . . . . . . . I 60. . . . . . . . . . . . . . . . I00

.

I

.

.

.

.

.

.

RECALCULATED. Milligrams of CUZO.

(3) Calculated from equation y = a +

(2)

20.

AS

Actually obtained in work.

bx+cx*.

33.9 63.5 93.1

33 -0 63.2 92.9 123.9 '54.1 180.6

(0

As given

in mi 'nal ta&.

33.9 63.7 93.4 123.1 153.0 182.7 212.6 242.3

122.6 152 .o

(5)

As given in recalculated table.

33.9 63.5 93 .o 122.6

I52 .o

181.3 181.3 210.6 210.6 239.8 239.7 239.4 180. . . . . . . . . . . . . . . . 268.0 269.0 272. I 268.9 200. . . . . . . . . . . . . . . . 297.1 298.0 302 .o 298.0 2 2 0 . . . . . . . . . . . .... 326.8 327 .o 331.7 326.9 2 40. . . . . . . . . . . . . . . . 356.1 355.9 361.6 355.9 2 6 0........ .. . . . 384.4 384.7 391.4 384.7 2 80. . . . . . . . . . . . . . 413.5 421.3 4'3.4 413.9 300. . . . . . . . . . . . . . . 443.1 451.1 442 * I 442.2 320. . , . . . . . . . . . . 470.8 481 .o 470.7 470.3 Columns I , 2 , and 3 are taken from Table 111, original article, THISJOURNAL,29, 544 (1907). Column 4 is taken from Table IV of the original article and as given in Bureau of Chemistry, Bull. 107,revised, pp. 243-251. , Column 5 is taken from Table I1 of this article. TABLEIL-TABLE FOR CALCULATING LACTOSE. [Expressed in milligrams.] 210.7

. . . . .. . . . .

cu-

Lactose.

cu-

prous oxide

(CuaO).

COP er (CUP.

IO I1 I2

8.9 9.8 10.7

13 I4

25

22.2

26 27 28 29

23.1 24.0 24.9 25.8

13.7 14.3 I5 .o 15.6 16.3

14.0 14.7 15 34 16.1 16.7

14.4 15.1 15.8 16.5 17.1

26.6 27.5 28.4 29.3 30.2

16.9 17.6 18.3 18.9 19.6

17.4 18.1

10.2

30 31 32 33 34

20. I

17.8 18.5 19.2 19.9 20.6

10.9 11.6 12.3 13 .o 13.7

35 36 37 38 39

31.1 32 .o 32.9 33.8 34.6

20.2

20.9

20.8 21.4

21.3 2 2 .o

21.5

22.1

22.7

22.2

22.8 23.5-

23.4 24.1

12.4

3.8 4.5 5.1 5.8 6.4

3.9 4.6 5.3 5.9 6.6

4.0 4.7 5.4 6.1 6.8

I5 16 17 18 19

13.3 14:2 15.1 16.0 16.9

7.1 7.8 8.4 9.1 9.7

7.3 8.0 8.6 9.3

7.5 8.2 8.9 9.5

10.0

20

17.8 18.7 19.5 20.4 L I .3

10.4

10.7 11.3

21

22

23 24

11.5

11.0

11.7 12.3

12.0

13.0

13.4

12.7

22.8

18.7 19.4

"FIE UNIFICATfON OF REDUCING SUGAR METHODS.

205

TABLEI1 (Continued). cu-

Lactose.

prous oxide (CUZO).

Copper (CU).

40 4' 42 43 44

35.5 36.4 37 - 3 38.2 39.1

24.2 24.8 25.5 26. I

45 46 47 48 49

40.0 40.9 41.7 42.6 43 ' 5

26.8 27.4 28.1 28.7 29.4

50 51 52 53 54

44.4 45.3 46.2 47.1 48.0

55 56 57 58 59 60 61 62 63 64

48.9 49.7 50.6 51.5 52.4 53.3 54.2 55.1 56 .o 56.8

65 66 67 68 69 70 71 72 73 74

75 76 77 78 79 80

81 82

83 84

7 -

(CmH2z (CIH220i1 OIJ.

$"10).

23.5

24. I 24.8

--

cuprous G Z H Z Z oxide OllH20). (CuzO).

Lactose. COP er (Cup.

85 86 87 88 89

75.5 76.4 77.3 78.2 79.1

27.5 28.2 28.9 29.5 30.2

24.8 25.4 26.1 26.8 27.5 28.2 28.9 29.6 30.3 31 .o

90 91

80.8

93 94

30.1 30.7 31.4 32. I 32.7

30.9 31.5 32.2 32.9 33.6

31.7 32.4 33.0 33.7 34.4

95 96 97 98 99

33.4 34.0 34.7 35.4 36.0

34.3 34.9 35.6 36.3 37 .o

35.1 35.8 36.5 37.2 37.9

36.7 37.3 38.0 38.6 39.3

37.6 38.3 39.0 39.7 40.3

57.7 58.6 59.5 60.4 61.3

40.0 40.6 41.3 41.9 42.6

41 .o 41.7 42.4 43.1 43.7

38.6 39.3 40.0 40.7 41.4 42.1 42 .a 43.5 44.2 44.8

62.2 63. I 64.0 64.8 65.7 66.6 67.5 68.4 69.3 70.2

43.3 43.9 44.6 45.2 45.9 46.6 47.2 47.9 48.5 49.2

44.4 45.1 45.8 46.4 47.1

71.1 71.9 72.8 73.7 74.6

49.9 50.5 51.2 51.8 52.5

47.8 48.5 49.1 49.8 50.5 51.2 51.9

25.5

26.2 26.8

52.5

53.2 53.9

56.0 56.6 57.3 58 .o 58.7

81.7 82.6 83.5

56.4 57.1 57.8 58.4 59.1

54.6 55.2 55.9 56.6 57.3 58.0 58.6 59.3 60.0 60.7

84.4 85.3 86.2 87 .o 87.9

59.7 60.4 61, I 61.7 62.4

61.3 62 .o 62.7 63.4 64.0

62.9 63.6 64.3 65 .o 65.7

Io0

88.8

I01

89.7 90.6 91.5 92.4

63 .o 63.7 64.4 65 .o 65.7

66.4 67. I 67.8 68.5 69.1

93.3 94.2 95 .o 95.9 96.8

66.4 67 .o 67.7 68.3 69.0

64.7 65.4 66. I 66.7 67.4 68.1 68.8 69.5 70. I 70.8

97.7 98.6 99.5

69.7 70.3 7 1 .o 71.6 72.3

71.5

73.3 74.0 74.7 75.4 76. I

73.0 73.6 74.3 75.0 75.6

74.9 75.6 76.2 76.9 77.6

76.3 76.9 77.6 78.3 78.9

78.3 79.0 79.6 80.3 81 .o

79.6 80.3 80.9 81.6 82.2

81.7 82.4 83.0 83.7 84.4

92

102

103

104

105 IO6

107 I08 I09 IIO I11

I I2

79.9

1x3 114

100.4

45.5 46.2 46.9 47.6 48.3

115 I 16 1I7 118 119

102. I

49 .o 49.7 50.4

I20

51.1

123 124

51.8

52.5 53.2 53.9 54.6 55.3

I2 I

I22

125 126 127

I28 129

101.3 103.0 103.9 104.8 105.7 106.6 107.5 108.4 109.3 110.1 111.0 111.9 112.8 113.7 114.6

53. 1

53.8 54.5 55.1 55.8

72.2

72.8 73.5 74.2

59.4 60.1 60.8 61.5 62.2

69.8 70.5 71.2

71.9 72.6

76.8 77.5 78.2 78.9 79.6 80.3 81 .o 81.7 82.4 83. I 83.8 84.5 85.2 85.9

86.6

PERCY H. WALKER.

T.mLE I1 (Continued). cu-

Lactose. Copper (CUI

82.9 116,4 83.6 117.2 84.2 118.1 84.9 119.0 85.5 86.2 119.9 86.9 120.8 121.7 87.5

115.5

122.6

88.2

123.5

88.9

124.4 125.2

126.1 127.o 127.9 128.8

129.7 130.6 131.5

132.3 133.2 134.1 135 . o 135.9 136.8

85.1

85.7 86.4 87.I 87.8 88.5

89.1 89.8 90.5 91.2

87.3 I75 88 .o 176 88.7 '77 89.4 178 90.I '79 90.8 I80 91.5 I 8 1 I82 92.I 92.8 183 93.5 184

89.5 90.2 90.8 91.5 92.2

91.9 92.5 93.2 93.9 94.6

94.2 94.9

92.8 93.5 94.2 94.8 95.5 96.I 96.8 97.5 98.I 98.8

95.3 95.9 96.6 97.3 98.0

97.7 98.4 99.I 99.8

99.5

137.7 138.6 139.5

100.8

140.3

101.5

141.2

102. I

100. I

142.I

102.8

143.0 143.9 144.8 145.7 146.6 '47.4 148.3 149.2 150. I

103.4

151 .o

109.4

151.9 152.8 '53.7 154.6

110.1

98.7 99.3 100.0

100.7 101.4 102. I

102.8 103.4 104. I 104.8

95.6

96.3 97 . o

100.5

'95 196 102.6 '97 103.3 198 104.0 '99 101.9

104.7 2 0 0 '05.4 201 106.1 2 0 2 106.8 203 '07.5 204

113.8 111.6 1'4.5

213

112.1

'25.7 126.4 127.I 127.8 128.5

125.3

I93 794

2 IO

212

214

112.3 1 1 5 . 2 215 216 113.0 "5.9 '13.7 116.6 217 218 114.3 "7.3 115.0 118.0 219

122.7

125.5)

123.4

126.6 127.3 I 2 8 .o 128.7

124.I

124.7 125.4 173.2 126.I 129.4 174.I 126.7 130.0 175.0 127.4 130.7 '75.9 1 2 8 . 1 131.4 176.8 128.7 1 3 2 . I 171.4

172.3

177,6 178.5 '79.4 180.3 181.2

129.4 130.0 130.7 131.4 132.o

182. I 132.7 183.0 '33.4 183.9 134.0 184.8 '34.7 185.6 135.4 186.5 136.0 '87.4 136.7 188.3 '37.4 189.2 138.0 190. I 138.7 191.o 139.4 191.9 140.0 192.7 140.7 '93.6 141.4 194.5 142.o

121.5

125.0

124.6

192

120.8

122.5

122.I

190 191

120.I

121.8

121.4

189

118.7 '19.4

119.1 1 2 2 . 2 119.8 122.9 123.6 120.5 121.3 124.3

120.7

211

111.4

117.1 117.8 118.4

167 . o 167.9 168.8 169.7 '70.5

109.6 1 1 2 . 4 110.3 113.1

110.8

114.1

158.1 114.8 159.0 115.4 159.9 116.1 160.8 116.7 161.7 "7.4 162.5 118.1 163.4 118.7

166. I

108.9

108.8

157.2

I88

106.8

110.9

116.4

123.2 123.9

106.I

108. I

"5.7

"3.4

164.3 "9.4 165.2 1 2 0 . 1

205 108.2 '05 ' 5 106.2 108.9 206 106.8 109.6 207 104. I 104.8 '07 .5 110.3 208 105.4 108.2 I l l .o 209

107.4

112.8

156.3

'85 I 86 '87

101.2

111.7

155.4

129.2 '29.9 130.6 '31.3 132.o

'32.7 133.4 '34.I '34.8 '35.5 132.8 136.2 133.5 136.9 134.1 137.6 134.8 138.3 '35.5 139.0 136.2 '39.7 136.9 740.4 137.6 141. I 141.8 138.3 138.9 '42.5 139.6 140.3 141 .o

141.7 142.4

143.0 143.7 '44.4 145, I 145.8

'43.2 '43.9 '44.6 145.3 146.0 146.7 '47.4 148.1 148.8 149.5

THE

207

UNIFICATION OP REDUCING SUGAR MRTHODS.

TABLEI1 (Coirtin UP&. cuprous oxide (CuzO). 220 22 I 222

223 224 225 226 227 228

229 2 30

23 I 232 233 234

195.4 196.3 197.2 198. I I99 .o

144.7 145.4

146.5 147.2 147.8 148.5 149.2

201.6 202.5 203.4

146 .o 146.7 147.4 148 .o 148.7

149.9 150.6 151.3 1 5 2 .o 152.6

204 . 3 205.2 206. I 207 .o 207.8

149.4 150.0 150.7 '51.4 152 .o

153.3

199.8 200.7

208.7 209.6 210.5 211.4 212.3

240 241 242 243 244

213.2 214. I 214.9 215.8 216.7

245 246 247 248

217.6 218.5 219.4 220.3

249

221.2

250

222. I

251 252 253 254

222.9 223.8 224.7 225.6

255 256 '57 259 260

261 262 263 264

Lactose

Copper (CUI.

235 236 237 238 239

258

cu-

Lactose.

142.7 143.4 144.0

154.0

'54.7 '55.4 156. I

150,~ 150.9 151.6 152.3 I53 .o

265 266 267 z 68 z 69

235.4 236.3 237.2 238.0 238.9

'53.7

270

239.8 240.7 241.6

154.4 271 755.1 155.8 156.5

272

273 '74

'42.5

243.4

157.2 157.9 158.6 159.3 160.0

275 276 277 278 279

244.3 245.1 246.0 246.9 247.8

160.7 161.4 162. I 162.8 163.5

2 80

248.7 249.6 250.5

152.7 '53.4 154.0 154.7 155.4 156.1 156.7 157.4 158.1 158.7

156.7 '57.4 158.1 158.8 159.5 160.2 160.9 161.5 162.2 162.9

164.3 165 .o 165.7 166.4 167. I

159.4 160.1 160.7 161.4 162. I

163.6 164.3 165 .o 165.7 166.3

167.8 168.5 169.2 '69.9 170.6

291 292 293 294

257.6 258.5 259.4 260.2 261. I

167 .o 167.7 168.4 169.1 169.8

'71.3 172 .o 172.7 '73.4 174. I

295 296 297 298 299

262 .o 262.9 263.8 264.7 265.6

226.5 227.4 228.3 229.2 230.0

162.7 163.4 164. I 164.7 165.4 166. I 166.8 167.4 168. I 168.8

170.5 171.1 171.8 172.5 173.2

'74.8 175.5 176.2 '76.9 177.6

300 30 I 302 303 304

266.5 267.4 268.2 269. I 270.0

230.9 231.8 232.7 233.6 234.5

169.4 170.1 170.8 171.4 172. I

173.9 '74.6 '75.3 176.0 176.6

178.3 179.0 179.8 180.5 181.2

305 306 307 308 309

270.9 271.8 272.7 273.6 274.5

281 282 283 2 84 285 2 86 287 288 2 89

2 90

172.8 173.5 174. I 174.8 '75.5 176. I 176.8 177.5 178.1 178.8 179.5 180.2 180.8 181.5 182.2

182.8

251.4

183.5 184.2 184.8

252.3

185.5

253. I 254.0 254.9 255.8 256.7

186.2 186.9 '87.5 188.2 188.9 189.5 190.2

190.9 191.5 192.2 192.9 193.6 194.2 '94.9 195.6 196.2 196.9 197.6 198.3 198.9 199.6 200.3 2 0 1 .o

201.6 202.3

'77.3 178.0 178.7 179.4 180. I

180.8 181.5 182. I 182.8 183.5

181.9 182.6 183.3 184.0 184.7 185.4 186.1

186.8 '87.5 188.2

184.2 184.9 185.6 186.3 187.0

188.9 189.6 190.3 191 .o 191.7

187.7 188.3 189.0 189.7 190.4 191. I 191.8 192.5 193.2 193.8

192.4 '93.1 193.9 194.6 195.3

194.5 195.2 195.9 196.6 197.3 198.o 198.7 199.3 200.0

200.7 201.4 202. I 202.8 203 . 5 204.2 204.9 205.5 206.2 206.9 207.6

196.0 196.7 '97.4 198.1 198.8 199.5 200.2 200.9 201.6 202.3

203.0

203.7 204.4 205. I 205.8 206.6 207.3 208 .o

208.7 209 .+ 210.1

210.8

211.5 212.2

212

.y

PSRCY H. WALKER.

208

cuprous oxide (CurO).

310 311 312 313 314

Copper (CU).

275.3 276.2 277, I 278.0 278.9

-

TABLEI1 (Colztilzued).

-

Lactose.

cu-

prous (GZHZZ (CIZHZ0 1 1 (C1zH z oxide COP er Old. +HzO\. OlcHzO?. (CUPO). CC"?.

203 .o 203.6 204.3 205.0

208.3 209.0 209.7 210.4

205.7

211.1

2'3.7 2'4.4 215.1 215.8 216.5

206.3

211.8

217.2

2 0 7 .o

212.5 213.1 213.8 2'4.5

217.9 218.6 219.3 220.0

215.2

220.7 221.4

Lactose.

--

(CIZHZZ( C I d h 0 ~ (~C I P H Z ~ Old. )HZO). O l l H ~ O f .

355 356 357 358 359

315.3 316.2 317. I 318.0 318.9

233.3 233.9 234.6 235.3 236.0

239.4 240. I 240.8 241 .5 242.2

245.6 246.3 247.0 247.7 248.4

3 60 36 I 362 363 364

319.8 320.6 321.5 322.4 323.3 324.2 325. I 326.0 326.9 327.8

242. I 242.7

242.9 243.6 244.3 245.0 245.7 246.4 247 .o 247.7 248.4 249. I

249.1 249.8 250.5

365 366 367 368 369

236.7 237.3 238 .o 238.7 '39.4 '240.0 240.7

370 37 I 372 373 374

328.6 329.5 330.4 33I..3 332.2

243.4 244.1 244.8 '45.4 246. I

249.8 250.5 251.2 251.9 252.6

252.7 253.4 254.1 254.8 255.5 256.2 256.9 257.7 258.4 259.1

315 316 317 318 319

279.8 280.7 281.6 282.5 283.3

320 32 I 322 323 324

284.2 285.1 286.0 286.9 287.8

211.7 212.4

325 326 327 329

288.7 289.6 290.4 291.3 292.2

213.1 213.7 214.4 215.1 215.8

220.7 221.4

330 331 332 333 334

293. I 294.0 294.9 295.8 296.7

216.4

222. I

227.8

217.1

222.8

217.8 218.4 219. I

375 376 377 378 379

333. I 334.0 334.9 335.7 336.6

246.8 247.5 248.1 248.8 249.5

253.3 254.0 254.7 255.4 256. I

259.8 260.5 261.2 261 . g 262.6

335 336 337 338 339

297.6 298.4 299.3 300.2 301. I

219.8 220.5

223.5 224.2 224.9 225.6 226.3

228.5 229.2 230.0 230.7

221. I

2 2 j .o

227.7 228.3

380 38 I 382 383 384

337.5 338.4 339.3 340.2 341. I

250.2

221.8 222.5

231.4 232. I 232.8 233.5 234.2

252.9

263.4 264. I 264.8 265,5 266.2

340 341 342 343 344

302 .o 302.9 303.8 304.7 305.5

223.2 223.8 224.5 225.2 225.9

229 .o

385 386 387 388 389

342 .o 342.9 343.7 344.6 345.5

253.6 254.2 254.9 255.6 256.3

266.9 267.6 268.3 269.0 269.8

345 346 347 348 349

306.4 307.3 308.2 309. I 310.0

226.5 227.2 227.9 228.5 229.2

232.5 233.2 233.9 234.6 235.3

390 39 I 392 393 394

346.4 347.3 348.2 349.1 350.0

270.5 271.2 271.9 272.6 273.3

310.9 311.8

229.9 230.6 231 . 2 231.9 232.6

235.9 236.6 237.3 238 .o 238.7

395 396 397 398 399

350.8 351.7 352.6 353.5 354.4

256.9 257.6 258.3 259.0 259.6 260.3 261 .o 261.7 262.3 263 .o

263.7 264.4 265. I 265.8 266.5

350 351 352 353 354

234.9 235.6 236.3 237.0 237.8 238. j 239.2 239.9 240.6 241.3 '242 . o 242.7 243.4 244. I 244.8

256.8 257.5 258. I 258.8 259.5 260.2 260.9 261.6 262.3 263.0

267.2 267,9 268.6 269.3 269.9

274.0 274.7 275.5 276.2 276.9

328

3'2.7

313.5 314.4

207.7 208.4 209 .o 209.7 210.4 2 1 1 .o

2'5.9 216.6 2'7.3 218.0

222.2

222.9 223.6

218.7 2'9.4

224.3

220. I

225.7 226.4 227. I

229.7 230.4 231. I 231.8

2 2 5 .o

241.4

250.8 251.5 252.2

251.2 252

.o

THE UNIFICATION OI: REDUCING SUGAR METHODS.

209

TABLBI1 (Continued). cu-

prous oxide Copper (CU,O). (CU).

Lactose.

355.3 356.2 357 ' I 358.0 358.8

263.7 264.4 265 .o 265.7 266.4

405 406 407 408 409

359.7 360.6 361.5 362.4 363.3

267. I 267.8

410 411 412 4. I3 414

364.2 365.1 365.9 366.8 367.7

4i5 416 417 418 419

368.6 369.5 370.4 371.3 372.2

273.9 274.6 275.2 275.9 276.6

420

373.1 373.9 374.8 375.7 376.6

277.3 277.9 278.6 279.3

425 426 427 428 429

377.5 378.4 379.3 380.2 381 .o

430 43 I 432 433 434

400 401 402

403

404

Lactose.

cu-

.

Copper (CUI.

(CizHzz 011).

270.6 271.3 272

.o

272.7

'73.4

--

(CizHz

OiiH20).

277.6 278.3 279.0 279.7 280.4

445 446 447 448 449

395.3 396. I 397.0 397.9 398.8

294.2 294.9 295.6 296.3 297 .o

302 .o 302. 7 303.4 304. I 304.8

309.7 310.5 311.2 311.9 312.6

281.1

399.7 400.6 401.5

297.6 298.3 299.0 299.7 300.4 301. I 301.7 302.4 303. I 303.8

305.5 306.2 306.9 307.6 308.3

313.3 314.0 314.7 :iI5.5 316.2

309.0 309.7 310.4 311.1 311.8

316.9 317.6 318..3 319.0 319.8

304.5 305 ' I 305.8 306.5 307.2

320. j 321.2 321.9 322.6 323.4 324.1 324.8 325.5 326.2 326.9

274. I 274.8 275.5 376.2 276.9

284.0

450 451 452 453 454

277.6 278.3 279.0 279.7 280.4

284.7' 285.4 286.2 286.9 287.6

455 456 457 458 4-59

281. I 282.5 283.2 283.9

288.3 289 .o 289.7 290.4 291.2

460 '461 462 463 464

404.1 405 .o 405.9 406.8 407 . 7 408.6 409.5 410.4 411.2 412. I

284.6 285.3 286.0 286.7 287.4

291.9 292.6 293.3 294 .o 294.7

465 466 467 468 469

413 .o 413.9 414.8 415.7 416.6

307.9 308.6 309.2 309.9 310.6

312.5 313.2 313.9 314.6 315.3 316.0 316.7 317.4 318.1 318.8

280.7 281.3

288. I

.o

282.7 283.4

289.4 290. I 290.8

295.4 296.2 296.9 297.6 298.3

470 471 472 473 474

4'7.5 418.4 419.2 420. I

311.3 312 .o 312.6 313.3 314.0

379.5 320.2 320.9 321.6 322.3

327.7 328.4 329.1 329.8 330.5

381.9 382.8 383.7 384.6 385.5

284. I 284.7 285.4 286. I 286.8

291.5 292.2 292.9 293.6 294.3

475 476 477 478 479

323.0 3'3.7 324.4 32.5. I 3258

331.3 332 .o 332.7 333.4 334. I

435 436 437 438 439

386.4 387.3 388.2 389 .o 389.9

287.5

289.5 290.2

295 .o 295.7 296.4 297.1 297.8

326.5 327.2 327.9 328.6 329.3

334.8 335.6 336.3 337 .o 337.7

440 441 442 443 444

390.8 391.7 392.6 393.5 394.4

290.9 291.5 292.2 292.9 293.6

298.5 299.5 299.9 300.6 301.3

299.0 299.7 300.5 301.2 301 , 9 302.6 303.3 304.0 304.7 305.5 306.2 306.9 307.6 308.3 309.0

330.0 330.7 331.4 332 * I 332.8 333.5

338.4 339.1 339.9 340 * 6 341 33 342 .o

42 1 42 2 423 424

268.4

269. I 269.8 270.5 271.2

271.8 272.5

273.2

280.0

282

288.1 288.8

281.8

288.8

281.9 282.6 283.3

402.4

403.3

421

.o

48 1 482 483 484

426,3 427-2 428.1 429 .o 429.9

314.7 315.4 316.1 316.7 3'7.4 318. I 318.8 319.5 320. I 320.8

485 486 487 488 489 490

430.8 431.7 432.6 433.5 434.3 435.2

321.5 322.2 322.9 323.6 324.2 324.9

480

421.9 422.8

423.7 424.6 425.5