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1.38 SECTION 1 tuted acid, respectively), -dithioc acid denotes [9C(S)]SH, and -thial denotes 9(C)HS (or -carbothialdehyde denotes 9CHS). When -carboxylic acid has been used for acids, the sulfur analog is named -carbothioic acid or -carbodithioic acid. Prefixes for the groups HS9 and RS9 are mercapto- and alkylthio-, respectively; this latter name may require parentheses for distinction from the use of thio- for replacement of oxygen in a trivially named acid. Examples of this problem are 4-C 2 H 5 9C 6 H 4 9CSOH named p- ethyl(thio)benzoic acid and 4-C 2 H 5 9S9C 6 H 4 9COOH named p-(ethylthio)benzoic acid. When 9SH is not the principal group, the prefix mercapto- is placed before the name of the parent compound to denote an unsubstituted 9SH group. The prefix thioxo- is used for naming "S in a thioketone. Sulfur analogs of acetals are named as alkylthio- or arylthio-. For example, CH 3 CH(SCH 3 )OCH 3 is 1-methoxy-1-(methylthio)ethane. Prefix forms for -carbothioic acids are hydroxy(thiocarbonyl)- when referring to the O-substituted acid and mercapto(carbonyl)- for the S-substituted acid. Salts are formed as with oxygen-containing compounds. For example, C 2 H 5 9S9Na is named either sodium ethanethiolate or sodium ethyl sulfide. If mercapto- has been used as a prefix, the salt is named by useof theprefix sulfido- for 9S . Compounds of thetypeR 1 9S9R 2 are named alkylthio- (or arylthio-) as a prefix to the name of R 1 or R 2 , whichever is the senior. Sulfonium Compounds. Sulfonium compounds of thetypeR 1 R 2 R 3 S X arenamed by citing in alphabetical order the radical names followed by -sulfonium and the name of the anion. For heterocyclic compounds, -ium is added to the name of the ring system. Replacement of CH by sulfonium sulfur is denoted by the prefix thionia-, and the name of the anion is added at the end. Organosulfur Halides. When sulfur is directly linked only to an organic radical and to a halogen atom, theradical nameis attached to theword sulfur and the name(s) and number of the halide(s) are stated as a separate word. Alternatively, the name can be formed from R9SOH, a sulfenic acid whose radical prefix is sulfenyl-. For example, CH 3 CH 2 9S9Br would be named either ethylsulfur monobromide or ethanesulfenyl bromide. When another principal group is present, a composite prefix is formed from the number and substitutive name(s) of the halogen atoms in front of the syllable thio. For example, BrS9COOH is (bromothio)formic acid. Sulfoxides. Sulfoxides, R 1 9SO9R 2 , are named by placing the names of the radicals in alphabetical order before the word sulfoxide. Alternatively, the less senior radical is named followed by sulfinyl- and concluded by the name of the senior group. For example, CH 3 CH 2 9SO9CH 2 CH 2 CH 3 is named either ethyl propyl sulfoxide or 1-(ethylsulfinyl)propane. When an SO group is incorporated in a ring, the compound is named an oxide. Sulfones. Sulfones, R 1 9SO 2 9R 2 , are named in an analogous manner to sulfoxides, using the word sulfone in placeof sulfoxide. In prefixes, the less senior radical is followed by -sulfonyl-. When the SO 2 group is incorporated in a ring, the compound is named as a dioxide. Sulfur Acids. Organic oxy acids of sulfur, that is, 9SO 3 H, 9SO 2 H, and 9SOH, arenamed sulfonic acid, sulfinic acid, and sulfenic acid, respectively. In subordinate use, the respective prefixes aresulfo-, sulfino, and sulfeno-. Thegrouping 9SO 2 9O9SO 2 9 or 9SO9O9SO is named sulfonic or sulfinic anhydride, respectively. Inorganic nomenclature is employed in naming sulfur acids and their derivatives in which sulfur is linked only through oxygen to the organic radical. For example, (C 2 H 5 O) 2 SO 2 is diethyl sulfate and C 2 H 5 O9SO 2 9OH is ethyl hydrogen sulfate. Prefixes O- and S- are used where necessary to denote attachment to oxygen and to sulfur, respectively, in sulfur replacement compounds. For example, CH 3 9S9SO 2 9ONa is sodium S-methyl thiosulfate. When sulfur is linked only through nitrogen, or through nitrogen and oxygen, to the organic radical, naming is as follows: (1) N-substituted amides are designated as N-substituted derivatives of thesulfur amides and (2) compounds of thetypeR9NH9SO 3 H may benamed as N-substituted
ORGANIC COMPOUNDS 1.39 sulfamic acids or by theprefix sulfoamino- to denotethegroup HO 3 S9NH9. Thegroups 9N"SO and 9N"SO 2 are named sulfinylamines and sulfonylamines, respectively. Sultones and Sultams. Compounds containing thegroup 9SO 2 9O9 as part of thering are called -sultone. The 9SO 2 9 group has priority over the 9O9 group for lowest-numbered locant. Similarly, the 9SO 2 9N" group as part of a ring is named by adding -sultam to the name of thehydrocarbon with thesamenumber of carbon atoms. The9SO 2 9 has priority over 9N" for lowest-numbered locant. 1.1.4 Stereochemistry Concepts in stereochemistry, that is, chemistry in three-dimensional space, are in the process of rapid expansion. This section will deal with only the main principles. The compounds discussed will be those that have identical molecular formulas but differ in the arrangement of their atoms in space. Stereoisomers is the name applied to these compounds. Stereoisomers can be grouped into three categories: (1) Conformational isomers differ from each other only in the way their atoms are oriented in space, but can be converted into one another by rotation about sigma bonds. (2) Geometric isomers are compounds in which rotation about a double bond is restricted. (3) Configurational isomers differ from one another only in configuration about a chiral center, axis, or plane. In subsequent structural representations, a broken line denotes a bond projecting behind the plane of the paper and a wedge denotes a bond projecting in front of the plane of the paper. A line of normal thickness denotes a bond lying essentially in the plane of the paper. 1.1.4.1 Conformational Isomers. A molecule in a conformation into which its atoms return spontaneously after small displacements is termed a conformer. Different arrangements of atoms that can be converted into one another by rotation about single bonds are called conformational isomers (see Fig. 1.1). A pair of conformational isomers can be but do not have to be mirror images of each other. When they are not mirror images, they are called diastereomers. FIGURE 1.1 Conformations of ethane. (a) Eclipsed; (b) staggered. Acyclic Compounds. Different conformations of acyclic compounds are best viewed by construction of ball-and-stick molecules or by use of Newman projections (see Fig. 1.2). Both types of representations are shown for ethane. Atoms or groups that are attached at opposite ends of a single bond should be viewed along the bond axis. If two atoms or groups attached at opposite ends of the bond appear one directly behind the other, these atoms or groups are described as eclipsed. That portion of the molecule is described as being in the eclipsed conformation. If not eclipsed, the atoms
Page 2 and 3: LANGE'S HANDBOOK OF CHEMISTRY John
Page 4 and 5: Grateful acknowledgment is hereby m
Page 6 and 7: PREFACE TO FIFTEENTH EDITION This n
Page 8 and 9: PREFACE TO FIFTEENTH EDITION ix inv
Page 10 and 11: xii PREFACE TO FOURTEENTH EDITION l
Page 12 and 13: PREFACE TO FIRST EDITION This book
Page 14 and 15: For the detailed contents of any se
Page 16 and 17: 1.2 SECTION 1 is derived from the G
Page 18 and 19: 1.4 SECTION 1 rather than methylide
Page 20 and 21: 1.6 SECTION 1 Styrene Toluene Xylen
Page 22 and 23: 1.8 SECTION 1 TABLE 1.2 Fused Polyc
Page 24 and 25: 1.10 SECTION 1 1.1.1.6 Bridged Hydr
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Page 36 and 37: 1.22 SECTION 1 When side chains of
Page 38 and 39: 1.24 SECTION 1 heterocyclic structu
Page 40 and 41: 1.26 SECTION 1 Bivalent radicals of
Page 42 and 43: 1.28 SECTION 1 Complex linear polya
Page 44 and 45: 1.30 SECTION 1 TABLE 1.11 Names of
Page 46 and 47: 1.32 SECTION 1 hydroxyamino- to the
Page 48 and 49: 1.34 SECTION 1 may be named (1) by
Page 50 and 51: 1.36 SECTION 1 Examples are methyl
Page 54 and 55: 1.40 SECTION 1 FIGURE 1.2 Newman pr
Page 56 and 57: 1.42 SECTION 1 from the ring are kn
Page 58 and 59: 1.44 SECTION 1 FIGURE 1.11 Two isom
Page 60 and 61: 1.46 SECTION 1 Chiral Center. The c
Page 62 and 63: 1.48 SECTION 1 FIGURE 1.15 Isomers
Page 64 and 65: 1.50 SECTION 1 entries to bring tog
Page 66 and 67: 1.52 SECTION 1 TABLE 1.13 Names and
Page 74 and 75: 1.60 SECTION 1 TABLE 1.14 Empirical
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Page 92 and 93: 2.4 SECTION 2 TABLE 2.1 Fundamental
Page 94 and 95: 2.6 SECTION 2 TABLE 2.1 Fundamental
Page 96 and 97: 2.8 SECTION 2 TABLE 2.2 Physical an
Page 98 and 99: 2.10 SECTION 2 TABLE 2.2 Physical a
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2.14 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. 25 1.2500
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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 Pressure
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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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3.62 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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Silver (argentum) Ag 47 [Kr] 4d 10
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PROPERTIES OF ATOMS,RADICALS,AND BO
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PROPERTIES OF ATOMS, RADICALS, AND
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SECTION 5 PHYSICAL PROPERTIES 5.1 S
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PHYSICAL PROPERTIES 5.3 5.1 SOLUBIL
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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(CHO 2 ) 2 26.2 28.0 29.9
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(III) sulfateCe 2 (SO 4 ) 3 ·9H 2
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iodidePbI 2 0.044 0.056 0.069 0.090
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Nickel sulfateNiSO 4 ·6H 2 O (pale
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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 10
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PHYSICAL PROPERTIES 5.25 TABLE 5.3
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PHYSICAL PROPERTIES 5.57 5.3 BOILIN
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TABLE 5.12 Ternary Azeotropic Mixtu
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TABLE 5.12 Ternary Azeotropic Mixtu
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PHYSICAL PROPERTIES 5.83 5.4 FREEZI
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PHYSICAL PROPERTIES 5.87 5.5 DENSIT
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PHYSICAL PROPERTIES 5.89 dt Dt P
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PHYSICAL PROPERTIES 5.135 5.6.1 Ref
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PHYSICAL PROPERTIES 5.137 where the
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PHYSICAL PROPERTIES 5.139 5.7 COMBU
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Temperature, C Substance 40 20 0 20
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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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THERMODYNAMIC PROPERTIES 6.143 The
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SECTION 7 SPECTROSCOPY 7.1 X-RAY ME
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SPECTROSCOPY 7.3 TABLE 7.1 Waveleng
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SPECTROSCOPY 7.9 TABLE 7.3 Critical
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SPECTROSCOPY 7.11 TABLE 7.4 X-Ray E
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SPECTROSCOPY 7.13 Emission line K 1
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SPECTROSCOPY 7.15 TABLE 7.7 Analyzi
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SPECTROSCOPY 7.17 TABLE 7.8 Mass Ab
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SPECTROSCOPY 7.19 TABLE 7.9 Electro
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SPECTROSCOPY 7.21 TABLE 7.11 Absorp
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SPECTROSCOPY 7.23 TABLE 7.13 Solven
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SPECTROSCOPY 7.25 7.3 FLUORESCENCE
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SPECTROSCOPY 7.27 TABLE 7.16 Fluore
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SPECTROSCOPY 7.29 TABLE 7.18 Detect
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SPECTROSCOPY 7.35 TABLE 7.19 Sensit
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SPECTROSCOPY 7.37 TABLE 7.19 Sensit
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SPECTROSCOPY 7.39 In terms of m ,
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SPECTROSCOPY 7.41 The ionization co
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SPECTROSCOPY 7.67 TABLE 7.28 Infrar
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7.69
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SPECTROSCOPY 7.71 7.6 RAMAN SPECTRO
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SPECTROSCOPY 7.73 TABLE 7.30 Raman
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SPECTROSCOPY 7.89 7.7 NUCLEAR MAGNE
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SPECTROSCOPY 7.91 TABLE 7.41 Nuclea
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SPECTROSCOPY 7.93 TABLE 7.42 Proton
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SPECTROSCOPY 7.95 TABLE 7.44 Estima
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SPECTROSCOPY 7.97 TABLE 7.46 Proton
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SPECTROSCOPY 7.99 TABLE 7.48 Solven
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SPECTROSCOPY 7.101 TABLE 7.49 Carbo
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SPECTROSCOPY 7.103 TABLE 7.51 Effec
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SPECTROSCOPY 7.107 TABLE 7.56 One-B
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SPECTROSCOPY 7.113 TABLE 7.63 Nitro
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SPECTROSCOPY 7.115 TABLE 7.64 Nitro
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SPECTROSCOPY 7.117 TABLE 7.69 Fluor
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SPECTROSCOPY 7.119 TABLE 7.72 Silic
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SPECTROSCOPY 7.121 TABLE 7.73 Phosp
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SPECTROSCOPY 7.123 TABLE 7.74 Phosp
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SPECTROSCOPY 7.125 when z 3 and y
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SPECTROSCOPY 7.127 Masses 19 and 31
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SPECTROSCOPY 7.129 TABLE 7.76 Conde
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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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3,3-Dimethoxybenzidine dihydrochlor
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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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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 pK a and Rh
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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
Page 1078 and 1079:
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
Page 1092:
SECTION 11 PRACTICAL LABORATORY INF
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11.4 SECTION 11 TABLE 11.2 Molecula
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11.6 SECTION 11 A saturated aqueous
Page 1099 and 1100:
11.8 SECTION 11 TABLE 11.6 Relative
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11.10 SECTION 11 11.3 BOILING POINT
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11.12 SECTION 11 TABLE 11.8 Organic
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11.14 SECTION 11 TABLE 11.9 Molecul
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11.4 SEPARATION METHODS TABLE 11.11
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11.18 SECTION 11 TABLE 11.12 Solven
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11.20 SECTION 11 TABLE 11.12 Solven
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TABLE 11.13 McReynolds’ Constants
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TABLE 11.13 McReynolds’ Constants
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11.26 SECTION 11 11.4.1 McReynolds
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11.28 SECTION 11 11.4.2.2 Partition
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11.30 SECTION 11 FIGURE 11.2 Band a
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11.32 SECTION 11 11.4.3 Ion-Exchang
Page 1125 and 1126:
11.34 SECTION 11 TABLE 11.16 Guide
Page 1127 and 1128:
11.36 SECTION 11 TABLE 11.16 Guide
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11.38 SECTION 11 TABLE 11.18 Relati
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11.40 SECTION 11 distribution coeff
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11.42 SECTION 11 TABLE 11.19 Gravim
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11.68 SECTION 11 TABLE 11.20 Elemen
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11.70 SECTION 11 TABLE 11.22 Common
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11.72 SECTION 11 TABLE 11.25 Tolera
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11.74 SECTION 11 TABLE 11.26 Heatin
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11.76 SECTION 11 TABLE 11.28 Titrim
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11.84 SECTION 11 appears becomes le
Page 1177 and 1178:
11.86 SECTION 11 TABLE 11.29 Equati
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11.88 SECTION 11 TABLE 11.29 Equati
Page 1181 and 1182:
11.90 SECTION 11 The more stable th
Page 1183 and 1184:
11.92 SECTION 11 11.6.6.2.5 Buffer
Page 1185 and 1186:
11.94 SECTION 11 TABLE 11.30 Standa
Page 1187 and 1188:
TABLE 11.32 Properties and Applicat
Page 1189 and 1190:
11.98 SECTION 11 TABLE 11.36 Maskin
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11.100 SECTION 11 TABLE 11.37 Anion
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11.102 SECTION 11 TABLE 11.39 Amino
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11.104 SECTION 11 TABLE 11.44 Facto
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11.106 SECTION 11 11.7 LABORATORY S
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11.108 SECTION 11 TABLE 11.48 Stand
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11.110 SECTION 11 Alizarin yellow G
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11.112 SECTION 11 Bromchlorophenol
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11.114 SECTION 11 p-Ethoxychrysoidi
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11.116 SECTION 11 Mercurous nitrate
Page 1209 and 1210:
11.118 SECTION 11 Potassium carbona
Page 1211 and 1212:
11.120 SECTION 11 until the ammoniu
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11.122 SECTION 11 TABLE 11.49 TLV C
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Page 1221 and 1222:
11.130 SECTION 11 TABLE 11.50 Chemi
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Page 1229 and 1230:
11.138 SECTION 11 of water which is
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TABLE 11.55 Thermoelectric Values i
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TABLE 11.56 Type B Thermocouples: P
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TABLE 11.58 Type J Thermocouples: I
Page 1237 and 1238:
TABLE 11.60 Type N Thermocouples: N
Page 1239 and 1240:
TABLE 11.62 Type S Thermocouples: P
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11.150 SECTION 11 11.11 CORRECTION
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Index Terms Links 2 Acid-base indic
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Index Terms Links 4 Alkynes, nomenc
Page 1247 and 1248:
Index Terms Links 6 Aurintricarboxy
Page 1249 and 1250:
Index Terms Links 8 Boron-11 chemic
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Index Terms Links 10 Cellulose acet
Page 1253 and 1254:
Index Terms Links 12 Collective ino
Page 1255 and 1256:
Index Terms Links 14 Degree Fahrenh
Page 1257 and 1258:
Index Terms Links 16 Electrical res
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Index Terms Links 18 Equivalent wei
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Index Terms Links 20 Fluorocarbon p
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Index Terms Links 22 Halogenated hy
Page 1265 and 1266:
Index Terms Links 24 Impact strengt
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Index Terms Links 26 Kα 1 lines, m
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Index Terms Links 28 Melmine phenol
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Index Terms Links 30 Neon-neon bond
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Index Terms Links 32 One-tailed tes
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Index Terms Links 34 Physical chemi
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Index Terms Links 36 Polyolefin the
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Index Terms Links 38 Pyridine: bina
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Index Terms Links 40 Rho values: fo
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Index Terms Links 42 Single-bond ra
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Index Terms Links 44 Stereoisomers
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Index Terms Links 46 Tension, aqueo
Page 1289 and 1290:
Index Terms Links 48 Triethylenetet
Page 1291 and 1292:
Index Terms Links 50 Water (Cont.)
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