LANGE'S HANDBOOK OF CHEMISTRY

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ORGANIC COMPOUNDS 1.3 ethane becomes the radical ethyl. These exceptions are permitted for unsubstituted radicals only: Isopropyl (CH3) 2CH9 Isopentyl (CH3) 2CHCH2CH29 Isobutyl (CH3) 2CHCH29 Neopentyl (CH3) 3CCH29 sec-Butyl CH3CH2CH(CH3)9 tert-Pentyl CH3CH2C(CH3) 29 tert-Butyl (CH3) 3C9 Isohexyl (CH3) 2CHCH2CH2CH29 Note the usage of the prefixes iso-, neo-, sec-, and tert-, and note when italics are employed. Italicized prefixes are never involved in alphabetization, except among themselves; thus sec-butyl would precede isobutyl, isohexyl would precede isopropyl, and sec-butyl would precede tert-butyl. Examples of alkane nomenclature are 2-Methylbutane (or the trivial name, isopentane) 3-Methylpentane (not 2-ethylbutane) 5-Ethyl-2,2-dimethyloctane (note cited order) 3-Ethyl-6-methyloctane (note locants reversed) 4,4-Bis(1,1-dimethylethyl)-2-methyloctane 4,4-Bis-1,1-dimethylethyl-2-methyloctane 4,4-Bis(tert-butyl)-2-methyloctane Bivalent radicals derived from saturated unbranched alkanes by removal of two hydrogen atoms are named as follows: (1) If both free bonds are on the same carbon atom, the ending -ane of the hydrocarbon is replaced with -ylidene. However, for the first member of the alkanes it is methylene
1.4 SECTION 1 rather than methylidene. Isopropylidene, sec-butylidene, and neopentylidene may be used for the unsubstituted group only. (2) If the two free bonds are on different carbon atoms, the straight-chain group terminating in these two carbon atoms is named by citing the number of methylene groups comprising the chain. Other carbon groups are named as substituents. Ethylene is used rather than dimethylene for the first member of the series, and propylene is retained for CH 3 9CH9CH 2 9 (but trimethylene is 9CH 29CH 29CH 29). Trivalent groups derived by the removal of three hydrogen atoms from the same carbon are named by replacing the ending -ane of the parent hydrocarbon with -ylidyne. 1.1.1.2 Alkenes and Alkynes. Each name of the corresponding saturated hydrocarbon is converted to the corresponding alkene by changing the ending -ane to -ene. For alkynes the ending is -yne. With more than one double (or triple) bond, the endings are -adiene, -atriene, etc. (or -adiyne, -atriyne, etc.). The position of the double (or triple) bond in the parent chain is indicated by a locant obtained by numbering from the end of the chain nearest the double (or triple) bond; thus CH 3CH 2CH"CH 2 is 1-butene and CH 3C#CCH 3 is 2-butyne. For multiple unsaturated bonds, the chain is so numbered as to give the lowest possible locants to the unsaturated bonds. When there is a choice in numbering, the double bonds are given the lowest locants, and the alkene is cited before the alkyne where both occur in the name. Examples: CH3CH2CH2CH2CH"CH9CH"CH2 1,3-Octadiene CH2"CHC#CCH"CH2 1,5-Hexadiene-3-yne CH3CH"CHCH2C#CH 4-Hexen-1-yne CH#CCH2CH"CH2 1-Penten-4-yne Unsaturated branched acyclic hydrocarbons are named as derivatives of the chain that contains the maximum number of double and/or triple bonds. When a choice exists, priority goes in sequence to (1) the chain with the greatest number of carbon atoms and (2) the chain containing the maximum number of double bonds. These nonsystematic names are retained: Ethylene CH 2"CH 2 Allene CH 2"C"CH 2 Acetylene HC#CH An example of nomenclature for alkenes and alkynes is 4-Propyl-3-vinyl-1,3-hexadien-5-yne Univalent radicals have the endings -enyl, -ynyl, -dienyl, -diynyl, etc. When necessary, the positions of the double and triple bonds are indicated by locants, with the carbon atom with the free valence numbered as 1. Examples: CH2"CH9CH29 2-Propenyl CH39C#C9 1-Propynyl CH39C#C9CH2CH"CH29 1-Hexen-4-ynyl These names are retained:
Page 1 and 2: LANGE'S HANDBOOK OF CHEMISTRY John
Page 3 and 4: Grateful acknowledgment is hereby m
Page 5 and 6: PREFACE TO FIFTEENTH EDITION This n
Page 7 and 8: PREFACE TO FIFTEENTH EDITION ix inv
Page 9 and 10: xii PREFACE TO FOURTEENTH EDITION l
Page 11 and 12: PREFACE TO FIRST EDITION This book
Page 13 and 14: For the detailed contents of any se
Page 15: 1.2 SECTION 1 is derived from the G
Page 19 and 20: 1.6 SECTION 1 Styrene Toluene Xylen
Page 21 and 22: 1.8 SECTION 1 TABLE 1.2 Fused Polyc
Page 23 and 24: 1.10 SECTION 1 1.1.1.6 Bridged Hydr
Page 25 and 26: 1.12 SECTION 1 TABLE 1.4 Suffixes f
Page 27 and 28: 1.14 SECTION 1 TABLE 1.5 Trivial Na
Page 29 and 30: 1.16 SECTION 1 TABLE 1.6 Trivial Na
Page 31 and 32: 1.18 SECTION 1 Selection of the pri
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Page 35 and 36: 1.22 SECTION 1 When side chains of
Page 37 and 38: 1.24 SECTION 1 heterocyclic structu
Page 39 and 40: 1.26 SECTION 1 Bivalent radicals of
Page 41 and 42: 1.28 SECTION 1 Complex linear polya
Page 43 and 44: 1.30 SECTION 1 TABLE 1.11 Names of
Page 45 and 46: 1.32 SECTION 1 hydroxyamino- to the
Page 47 and 48: 1.34 SECTION 1 may be named (1) by
Page 49 and 50: 1.36 SECTION 1 Examples are methyl
Page 51 and 52: 1.38 SECTION 1 tuted acid, respecti
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Page 55 and 56: 1.42 SECTION 1 from the ring are kn
Page 57 and 58: 1.44 SECTION 1 FIGURE 1.11 Two isom
Page 59 and 60: 1.46 SECTION 1 Chiral Center. The c
Page 61 and 62: 1.48 SECTION 1 FIGURE 1.15 Isomers
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Page 65 and 66: 1.52 SECTION 1 TABLE 1.13 Names and
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1.54 SECTION 1 TABLE 1.13 Names and
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1.60 SECTION 1 TABLE 1.14 Empirical
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2.2 SECTION 2 2.3.6 Student’s Dis
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2.4 SECTION 2 TABLE 2.1 Fundamental
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2.6 SECTION 2 TABLE 2.1 Fundamental
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2.8 SECTION 2 TABLE 2.2 Physical an
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2.10 SECTION 2 TABLE 2.2 Physical a
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2.24 SECTION 2 TABLE 2.3 Mathematic
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2.26 SECTION 2 TABLE 2.6 Abbreviati
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2.36 SECTION 2 TABLE 2.7 Conversion
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2.54 SECTION 2 TABLE 2.8 Temperatur
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2.66 SECTION 2 2.1.1 Conversion of
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2.68 SECTION 2 Oleometer. A hydrome
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2.70 SECTION 2 Example 3. To find t
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2.72 SECTION 2 TABLE 2.9 Barometer
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2.74 SECTION 2 TABLE 2.9 Barometer
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2.76 SECTION 2 TABLE 2.10 Barometri
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2.78 SECTION 2 TABLE 2.12 Reduction
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2.80 SECTION 2 TABLE 2.12 Reduction
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2.82 SECTION 2 TABLE 2.13 Viscosity
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2.84 SECTION 2 TABLE 2.14 Conversio
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2.86 SECTION 2 TABLE 2.15 Hydromete
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2.88 SECTION 2 TABLE 2.17 Correctio
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2.90 SECTION 2 TABLE 2.18 Molar Equ
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2.92 SECTION 2 TABLE 2.19 Factors f
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2.94 SECTION 2 TABLE 2.19 Factors f
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2.96 SECTION 2 TABLE 2.20 Values of
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2.98 SECTION 2 TABLE 2.21 Transmitt
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2.100 SECTION 2 TABLE 2.21 Transmit
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2.102 SECTION 2 2.2 MATHEMATICAL TA
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2.104 SECTION 2 TABLE 2.23 Derivati
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2.106 SECTION 2 TABLE 2.24 Integral
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2.108 SECTION 2 TABLE 2.24 Integral
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2.110 SECTION 2 Regular Polygon of
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2.112 SECTION 2 A h[0.4(y y ) 1.
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2.114 SECTION 2 2.2.3.1 Signs of th
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2.116 SECTION 2 x2 x3 x4 x5 ln(1 x
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2.118 SECTION 2 2.3.2 Errors in Qua
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2.120 SECTION 2 The breadth or spre
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2.122 SECTION 2 TABLE 2.26b Areas U
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2.124 SECTION 2 The distribution of
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2.126 SECTION 2 Should there be mor
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2.128 SECTION 2 Example 10 Six samp
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2.130 SECTION 2 2.3.9 The F Statist
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TABLE 2.29 F Distribution (Continue
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2.134 SECTION 2 mathematical treatm
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2.136 SECTION 2 The confidence limi
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2.138 SECTION 2 situation where rel
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3.2 SECTION 3 The alphabetical orde
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3.4 SECTION 3 When it is required t
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3.6 SECTION 3 PO phosphoryl SeO sel
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3.8 SECTION 3 3.1.5 Acids 3.1.5.1 A
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3.10 SECTION 3 3.1.6.6 Multiplicati
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3.12 SECTION 3 3.2 PHYSICAL PROPERT
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TABLE 3.2 Physical Constants of Ino
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3.16 TABLE 3.2 Physical Constants o
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3.62 SECTION 3 TABLE 3.3 Synonyms a
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SECTION 4 PROPERTIES OF ATOMS, RADI
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4.3 Fermium Fm 100 [Rn] 5f 12 7s 2
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4.5 Silver (argentum) Ag 47 [Kr] 4d
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PROPERTIES OF ATOMS,RADICALS,AND BO
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PROPERTIES OF ATOMS, RADICALS, AND
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TABLE 4.5 Electronegativities of th
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TABLE 4.11 Bond Dissociation Energi
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TABLE 4.16 Table of Nuclides (Conti
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SECTION 5 PHYSICAL PROPERTIES 5.1 S
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5.1 SOLUBILITIES PHYSICAL PROPERTIE
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TABLE 5.1 Solubility of Gases in Wa
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TABLE 5.1 Solubility of Gases in Wa
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TABLE 5.2 Solubilities of Inorganic
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formateBa(CHO2) 2 26.2 28.0 29.9 31
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(III) sulfateCe2(SO4) 3 ·9H2O 21.4
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iodidePbI2 0.044 0.056 0.069 0.090
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Nickel sulfateNiSO4 ·6H2O (pale bl
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Praseodymium bromatePr(BrO 3) 3 55.
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formate NaCHO 2 43.9 62.5 81.2 102
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Uranyl nitrate UO 2(NO 3) 2 98 107
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TABLE 5.3 Vapor Pressure of Mercury
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TABLE 5.4 Vapor Pressure of Ice in
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TABLE 5.6 Vapor Pressure of Water (
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TABLE 5.8 Vapor Pressures of Variou
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PHYSICAL PROPERTIES 5.33 TABLE 5.8
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5.3 BOILING POINTS TABLE 5.10 Boili
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TABLE 5.11 Binary Azeotropic (Const
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TABLE 5.12 Ternary Azeotropic Mixtu
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5.4 FREEZING MIXTURES TABLE 5.13 Co
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TABLE 5.13 Compositions of Aqueous
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5.5 DENSITY AND SPECIFIC GRAVITY TA
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PHYSICAL PROPERTIES 5.89 d D t t
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5.6.1 Refractive Index PHYSICAL PRO
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PHYSICAL PROPERTIES 5.137 where the
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5.7 COMBUSTIBLE MIXTURES TABLE 5.23
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TABLE 5.23 Properties of Combustibl
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Deuterium 1150 1222 1297 1372 1448
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TABLE 5.25 Liquid Thermal Conductiv
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TABLE 5.26 Thermal Conductivity of
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TABLE 5.29 Van der Waals’ Constan
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TABLE 5.30 Triple Points of Various
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PHYSICAL PROPERTIES 5.171 This equa
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SECTION 6 THERMODYNAMIC PROPERTIES
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THERMODYNAMICPROPERTIES 6.3 6.1.1.2
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THERMODYNAMICPROPERTIES 6.5 A gener
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THERMODYNAMICPROPERTIES 6.7 TABLE 6
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THERMODYNAMICPROPERTIES 6.9 TABLE 6
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THERMODYNAMICPROPERTIES 6.11 TABLE
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THERMODYNAMIC PROPERTIES 6.21 TABLE
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THERMODYNAMIC PROPERTIES 6.101 TABL
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PClF 3 THERMODYNAMIC PROPERTIES 6.1
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THERMODYNAMIC PROPERTIES 6.143 The
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TABLE 6.5 Critical Properties (Cont
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SECTION 7 SPECTROSCOPY 7.1 X-RAY ME
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TABLE 7.1 Wavelengths of X-Ray Emis
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SPECTROSCOPY 7.5 TABLE 7.1 Waveleng
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TABLE 7.2 Wavelengths of Absorption
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TABLE 7.3 Critical X-Ray Absorption
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TABLE 7.4 X-Ray Emission Energies i
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SPECTROSCOPY 7.13 Emission line K 1
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TABLE 7.7 Analyzing Crystals for X-
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SPECTROSCOPY 7.17 TABLE 7.8 Mass Ab
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TABLE 7.9 Electronic Absorption Ban
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TABLE 7.11 Absorption Wavelength of
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SPECTROSCOPY 7.23 TABLE 7.13 Solven
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7.3 FLUORESCENCE TABLE 7.16 Fluores
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SPECTROSCOPY 7.27 TABLE 7.16 Fluore
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TABLE 7.18 Detection Limits in ng/m
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TABLE 7.19 Sensitive Lines of the E
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TABLE 7.19 Sensitive Lines of the E
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In terms of m, the wavenumber of m
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The ionization constant can be calc
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SPECTROSCOPY 7.43 TABLE 7.20 Absorp
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TABLE 7.22 Absorption Frequencies o
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TABLE 7.27 Absorption Frequencies i
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TABLE 7.28 Infrared Transmitting Ma
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7.69
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7.6 RAMAN SPECTROSCOPY SPECTROSCOPY
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SPECTROSCOPY 7.73 TABLE 7.30 Raman
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SPECTROSCOPY 7.75 TABLE 7.30 Raman
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TABLE 7.32 Raman Frequencies of Cum
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TABLE 7.33 Raman Frequencies of Car
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TABLE 7.34 Raman Frequencies of Oth
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TABLE 7.35 Raman Frequencies of Aro
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TABLE 7.36 Raman Frequencies of Sul
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TABLE 7.39 Raman Frequencies of Mis
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7.7 NUCLEAR MAGNETIC RESONANCE TABL
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TABLE 7.41 Nuclear Properties of th
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TABLE 7.42 Proton Chemical Shifts (
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SPECTROSCOPY 7.95 TABLE 7.44 Estima
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TABLE 7.46 Proton Spin Coupling Con
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SPECTROSCOPY 7.99 TABLE 7.48 Solven
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TABLE 7.49 Carbon-13 Chemical Shift
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SPECTROSCOPY 7.103 TABLE 7.51 Effec
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TABLE 7.54 Carbon-13 Chemical Shift
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TABLE 7.56 One-Bond Carbon-Hydrogen
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TABLE 7.58 Carbon-Carbon Spin Coupl
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7 Li CH3Li 15 SPECTROSCOPY 7.111 TA
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TABLE 7.63 Nitrogen-15 (or Nitrogen
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TABLE 7.64 Nitrogen-15 Chemical Shi
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TABLE 7.69 Fluorine-19 Chemical Shi
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TABLE 7.72 Silicon-29 Chemical Shif
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TABLE 7.73 Phosphorus-31 Chemical S
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TABLE 7.74 Phosphorus-31 Spin Coupl
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when z 3 and y 1. The empirical f
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Masses 19 and 31 Alcohol Mass 66
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TABLE 7.76 Condensed Table of Mass
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SECTION 8 ELECTROLYTES, ELECTROMOTI
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ELECTROLYTES, EMF, AND CHEMICAL EQU
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TABLE 8.7 Proton Transfer Reactions
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TABLE 8.7 Proton Transfer Reactions
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TABLE 8.9 Selected Equilibrium Cons
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8.75 3-tert-Butylbenzoic acid (0) 4
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4-Hydroxyproline (1) 1.900 1C 1.850
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N-Propionylglycine (1) 3.728 3.723
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TABLE 8.14 National Bureau of Stand
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1 part 0.1% neutral red in alc. * V
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TABLE 8.25 Fluorescent Indicators (
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3,3-Dimethoxybenzidine dihydrochlor
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8.7 CONDUCTANCE ELECTROLYTES, EMF,
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TABLE 8.35 Equivalent Conductivitie
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KCl 127.3 124.4 122.4 115.8 112.0 1
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NaIO 3 75.2 72.6 70.9 64.4 60.5 1
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Conductance of an Electrolyte Solut
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9.2 SECTION 9 9.1 LINEAR FREE ENERG
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9.4 SECTION 9 TABLE 9.1 Hammett and
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9.6 SECTION 9 TABLE 9.1 Hammett and
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9.8 SECTION 9 TABLE 9.3 pKa and Rho
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10.2 SECTION 10 10.4.6 Polyacrylate
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10.4 SECTION 10 10.2 ADDITIVES TO P
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10.6 SECTION 10 injection molding.
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10.8 SECTION 10 10.3 FORMULAS AND K
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10.10 SECTION 10 Key properties of
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10.12 SECTION 10 10.3.8 Fluorocarbo
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10.14 SECTION 10 10.3.11 Phenolics
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10.16 SECTION 10 The resin has the
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10.18 SECTION 10 10.3.19 Polyuretha
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10.20 SECTION 10 10.3.22 Sulfones B
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TABLE 10.2 Properties of Commercial
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10.58 SECTION 10 10.4 FORMULAS AND
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10.60 SECTION 10 10.4.8 Polychlorop
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10.62 SECTION 10 Styrene-butadiene
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10.5 CHEMICAL RESISTANCE TABLE 10.4
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10.6 GAS PERMEABILITY TABLE 10.5 Ga
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TABLE 10.5 Gas Permeability Constan
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TABLE 10.7 Constants ofFats and Oil
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TABLE 10.8 Constants ofWaxes Wax Me
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SECTION 11 PRACTICAL LABORATORY INF
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11.1 COOLING TABLE 11.1 Cooling Mix
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11.2 DRYING AND HUMIDIFICATION TABL
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PRACTICAL LABORATORY INFORMATION 11
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TABLE 11.7 Relative Humidity from D
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3-Methyl-1-butanol 132.0 Cyclohexyl
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TABLE 11.9 Molecular Elevation of t
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TABLE 11.11 Solvents of Chromatogra
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TABLE 11.13 McReynolds’ Constants
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FIGURE 11.1 Profile of a solute ban
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TABLE 11.16 Guide to Ion-Exchange R
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TABLE 11.16 Guide to Ion-Exchange R
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11.5 GRAVIMETRIC ANALYSIS TABLE 11.
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TABLE 11.19 Gravimetric Factors (Co
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Sodium tetraphenylborate, NaB(C 6H
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TABLE 11.24 Porosities of Fritted G
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TABLE 11.26 HeatingTemperatures, Co
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TABLE 11.28 Titrimetric (Volumetric
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HN 3 PRACTICAL LABORATORY INFORMATI
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11.6.5 Precipitation Titrations PRA
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TABLE 11.31 Indicators for Precipit
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TABLE 11.33 Variation of 4 with pH
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TABLE 11.38 Common Demasking Agents
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TABLE 11.41 Pipet Capacity Toleranc
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TABLE 11.45 Cubical Coefficients of
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TABLE 11.48 Standard Stock Solution
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TABLE 11.48 Standard Stock Solution
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11.8 SIEVES AND SCREENS TABLE 11.53
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TABLE 11.55 Thermoelectric Values i
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TABLE 11.57 Type E Thermocouples: N
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TABLE 11.59 Type K Thermocouples: N
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TABLE 11.61 Type R Thermocouples: P
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TABLE 11.63 Type T Thermocouples: C
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Index Terms Links Abbreviations: of
Page 1243 and 1244:
Index Terms Links Aggregation, stat
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Index Terms Links Anions, inorganic
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Index Terms Links Benzoylacetone, f
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Index Terms Links Carbon-carbon: bo
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Index Terms Links Chemical shifts:
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Index Terms Links Correction for so
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Index Terms Links Dielectric streng
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Index Terms Links Emergent stem cor
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Index Terms Links Excitation wavele
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Index Terms Links Gases: equations
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Index Terms Links Hydrogen: binary
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Index Terms Links Iodine: bond diss
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Index Terms Links Lithium: bond dis
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Index Terms Links Mode for set of n
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Index Terms Links Nitrogen-oxygen d
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Index Terms Links Peak asymmetry fa
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Index Terms Links Polybutylene poly
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Index Terms Links Precipitates, hea
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Index Terms Links Rankine scale, co
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Index Terms Links Selection rules:
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Index Terms Links Specific gravity:
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Index Terms Links Sulfuric acid sol
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Index Terms Links Thiosulfate: form
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Index Terms Links Vaporization: ent
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Index Terms Links Zincon, formation
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LANGE'S HANDBOOK OF CHEMISTRY

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