第十四章含氮有机化合物 (10 学时)
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(1014.114.214.314.414.514.6
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14.714.814.914.1014.11
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C-N N-N N-O C=N N=N N=O CN NN N-H ?
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14.1 (-NO2) R-NO2 Ar-NO2,,
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14.1CH3NO2NO2CH3-CH-CH32-
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14.114.1.1 N=ONO
NO0.122nmO-N-O127P-Nsp2 34-I,-C
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14.114.1.2 :
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14.114.1.2:
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14.1 14.1.3 1.,, :
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14.1 14.1.3 1. TNT
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14.114.1.31.:
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14.1 14.1.3 1.1
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14.114.1.32.- ,--I-C--(-C) -pKa10,
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14.114.1.32.- ,-,
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14.114.1.32.(2)
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14.114.1.32.(2)
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14.1 14.1.3 2. (2) , :
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14.114.1.32.(2)
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14.114.1.32.(2)
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14.114.1.32.(2) (a)
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14.114.1.32.(2) (a)
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14.114.1.32.(2) (b)N-
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14.114.1.32.(2) (b)
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14.114.1.32.(2) (b)
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14.114.1.32.(2) (c)
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14.114.1.3:
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14.1(88%)(c)
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14.114.1.32.(2) ,,
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14.114.1.32.(2)
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14.114.1.32.(2) -P287
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14.114.1.32.(2)
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14.114.1.32.(3) ,,,,-
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14.114.1.32.(3)
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P288----1
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14.114.1.32.(4) ,,,
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14.114.1.32.(4):,.
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14.114.1.32.(4):
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14.114.1.32.(4):
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14.114.1.32.(4):
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14.114.1.32.(4):
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14.114.1.32.(4):
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()2.(4)
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289
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14.2 14.2.1 ,()()()
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14.214.2.1
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14.214.2.1:NH3RNH2R2NHR3N
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14.2 14.2.1 ,,,
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14.214.2.1:
H2NCH2CH2NH2C2H5NH2()()()
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14.214.2.1 (NH4)+X-, :[N(CH3)4]+I-(NH4)+OH-,:[N(CH3)4]+OH-
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CH3NH214.214.2.2- , , :
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CH3NHC2H514.2-14.2.2- ,, :
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(CH3)2NH(C2H5)3N14.214.2.2- , :
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14.22,5-14.2.2- ,, :
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14.214.2.2- ,, :
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14.2N-N,N-N--N-14.2.2- ,,N :
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14.22-14.2.2- , :
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14.22,5--3-2-14.2.2- :
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14.22,5--3-N--2-14.2.2- :
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[(CH3)4N]+I-[CH3(CH2)11N(CH3)3]+Br-14.214.2.2 :
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P292----2 N- 44- N-- NN- 2--5- 6-- NN--3- NN---
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14.2.3 Nsp3N,Nsp3 14.2
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14.2.3 Nsp3 -NH2+C-I,,
14.278
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14.3.1 ,14.3
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14.3.1 ,;;14.3
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14.314.3.1 ,
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14.3.12. 14.3
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14.3.12. 14.3
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14.3.21. 14.3
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14.3.22. ,, :14.3
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14.314.3.22. :RRCH-NH2()
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14.3.22. ,,()14.3
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14.3.22. :14.3
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14.3.23. , :14.3
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14.3 14.3.2 3. : ,-66
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14.314.3.23.:
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14.314.3.23. ()
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P294----3,4,5
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14.4.1,,,,-14.4
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14.4.1 , :14.4
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14.4.1,,,,,14.4
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14.4.1:14.4 CH3OCH3 CH3NHCH3 CH3CH2NH2 CH3CH2OH HCOOH 46 45 45 46 46
/ -24 7.5 17 78 101
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14.4.114.4,,,
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P321---191-8215
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14.5 14.5.1-NH2 ,
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14.514.5.1,:pKb=3-5pKb=7-10NH3pKb=4.76
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14.5 (CH3)2NH > CH3NH2 > (CH3)3N > NH3pKb 3.27 3.38 4.21 4.7614.5.1:(1),,: >>> -p ,,:
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14.514.5.1(2),:,
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14.514.5.1(2),:
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14.514.5.1(3),,:
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14.5 14.5.1 ,, :
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14.5 14.5.1 ,, : ,,
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P298----7,8,97NaOH,H2O8-NH2 9-NO2-I-C-NH2
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14.5 14.5.2 ,,
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14.5 14.5.2 :
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14.5 14.5.2 ,11.2N-
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14.5 14.5.2,: ,,
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14.5 14.5.2 , -N--- :-D
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14.5 14.5.3 ,,N-,
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14.5 14.5.3,
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14.5 14.5.3 ,, :>> :
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14.514.5.3: ,,,
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14.5 14.5.3 , :N-N-
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14.5 14.5.3N-P300,,
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14.5 14.5.3 :
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14.5 14.5.3 (),,,,
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14.5 14.5.3 :
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14.5NaOH/H2O:14.5.3
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14.5RNH2R2NHR3NHClNaOHR3N ()HClRNH2R2NH:
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14.51 6 NaOH KOH 2 C6H 5SO2 C1 3 4 KOHNaOH
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14.5 14.5.4, , , 10
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14.5 14.5.4N- N-,
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14.5 14.5.4N-,,
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14.5 14.5.4,,
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14.514.5.4
NaNO2/HClN2 ()
N2 ()
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14.514.5.51. ,,,
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14.5 14.5.5 1. ,,,,
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14.514.5.52. ,,,,,,
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14.514.5.52.:
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14.514.5.52. ,,, ,
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14.514.5.53. ,,,,180
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14.514.5.53.
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14.514.5.53. ,,
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14.514.5.53. ,,,
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14.5 14.5.6 ,,,
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14.514.5.6
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14.514.5.6
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:
Br2/H2OFeCl3
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P303----10,11,12
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303,.
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P321---20213 2223
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14.714.7.1, ,,
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14.714.7.2 NaCN
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14.714.7.2
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14.714.7.215-25
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14.714.7.2 CH2Cl + KCNCH3CN,18--6(100%)CH2CN25,0.4h
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14.7 14.7.2 , :
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14.7 14.7.3R4N+OH-,,,,,
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14.714.7.3-,-,
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14.714.7.3-,P151
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P30713CH2=CHCH2CH2CH2-N(CH3)214-
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14.8 ,(),
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14.814.8.1,(-SO3-Na+)(-OSO2O-Na+)[-OPO(O-Na+)2](-COO-Na+)(),,C10-C18
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14.814.8.2 ,,
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14.814.8.2 ,,:
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14.814.8.2,, C12-C18 ,
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14.814.8.2AlCl3,1-1--,,
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14.814.8.22.
HCl[C12H25N(CH3)3]+Cl-
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14.814.8.22.
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14.8.2 3. -COO--SO3--OSO3-NN--N-14.8
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14.8.2 3. 14.8
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14.814.8.24. ()
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14.814.8.24.
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121424
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14.9
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14.914.9.11.
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14.914.9.11.
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14.91.
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14.914.9.11.
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14.914.9.1.COOH,-O-P(OH2),
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14.914.9.1.
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14.914.9.13. () -NR3OH- +
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14.914.9.1 3.
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14.9
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14.914.9.13.
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14.914.9.14. Cl-SO42-NO3-
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14.914.9.2 311
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14.10-N=N-,,:-N=N-,,:
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14.10 , :
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14.1014.10.1 , ,
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14.1014.10.1 KI-HNO2I-I2,
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P312----14
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14.1014.10.2 ,,,,
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14.1014.10.3. (1) ,,:
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14.1014.10.3. (1) ,,,:
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14.1014.10.3. (1) ,,,:
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14.1014.10.3. (2) ,
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14.1014.10.3. (2) :
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14.1014.10.3. (3) (H3PO2),,:
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14.1014.10.3. (3) : ,
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14.1014.10.3. (3) ,,,:
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14.10Fe+HCl
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14.1014.10:1,3,5-
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P314----15
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14.1014.10. (1) X-
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14.1014.10.3. (1)
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14.1014.10.3. (2) ,,4-
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14.1014.10.3. (2) ,
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14.10:
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14.10,:
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14.10 pH4.4,:
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14.10 (Na2S2O4),:
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P317---161718
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14.11 14.11.1CH3CNCH2=CH-CN
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14.11.1NCCH2CH2CH2CH2CN14.11
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14.11.1. (1)14.11
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14.11.1. (1)14.11
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14.11.1. (2)14.11
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14.11.1. (3)14.11
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14.11.1. (4)(14.11
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14.11.3. 55 60 58 59 97.0 97.2 56.5 4914.11
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14.11.1. 14.11
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14.11.1. 14.11
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14.11.1. 14.11
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14.11.1.,3-14.11
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14.11.2 N=C=O)14.11
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14.11.2 14.11
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14.11.214.11 4-13-
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14.11.2 14.11
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14.11.2-2,4-14.11
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14.11.2 CO214.11
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- 14.11 P320
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P320 14.11
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P322---26293031323334
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P321---21(3)67P322---24(4), 2728
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A B C
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P303----12(2)
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HNO3,H2SO4(CH3CO)2OBr2/H2OFe + HClH2OOH-
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P303----12(3)3
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-SO2-)-SO-)
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