INDEX acidic regions reaction to form esters 835 A strong acid–strong base/strong base–strong absolute temperatures 299 reaction with acid anhydrides 1031 absolute uncertainties 35, 37–8 acid 473–4 reaction with acid chlorides 1031 absorbance (A) of light 575 weak acid–strong base/weak base–strong reaction with active metals 828 absorption spectra 127–8 acid 476 reaction with carboxylic acid accuracy of measurement 32–3 acidic solutions 437 derivatives 1031–2 acetaldehydes 945 alcohols 827 reaction with carboxylic acids 1028–31 acetals 955, 957–8 redox reactions in 501–3 reaction with esters 1031 as carbonyl-protecting groups 959 thiols 846–7 reaction with phosphorus halides 830 formation of 958, 993–5 acidity constants (Ka) 447 See also reaction with thionyl chlorides 830 acetic acids 433, 464, 466 Henderson–Hasselbalch equation from reduction of carbonyl compounds 826 in buffer solutions 467–8 secondary (2°) 823 Ka 447–8 esters 1010 determining values 449 solubility 1018 speciation diagrams 478 acidophiles 430 structural formula 55–6 vapour pressure variations 262 acids 432 See also diprotic acids; monoprotic tertiary (3°) 823 acids; strong acids; weak acids aldehydes 770, 833 acetones 1 13 boiling points 248–9 amino acids 1066–8 H-NMR and C-NMR spectra 913 calculating vapour pressure 413 bond enthalpies 461 acid-catalysed hydrations 956–8 electron density models 948 common 433 addition of alcohols 955–9 industrial uses 949 dissociation in aqueous solutions at 25° 462 addition of Grignard reagents 953–4 acetophenones 949, 950, 970 maximum strength 465 addition of carbon nucleophiles 955 acetylenes 716 molecular basis of strength 461–5 aliphatic 949 achiral compounds 761, 765, 772 See also oxoacids 462–4 aromatic 949 meso compounds polyprotic 433, 447, 479 boiling points 1018 achiral enols 970 strengths of 441–2 catalytic reductions 965 achiral isomers 773 superacids 465, 482 formation of imines 960–1 acid anhydrides 835, 1012 triprotic 461 formation of oximes and hydrazones 962 hydrolysis 1032, 1035 actins 1060 formation of tetrahedral carbonyl addition nomenclature 1016 actinoids 16, 548, 602 intermediates 951, 966 reaction with alcohols 1031, 1032 activation energies (Ea) 665, 666, 667 a-halogenation 970–1 reaction with ammonia and amines calculating from two rate constants 670 from hydration of alkynes 950–1 1036, 1037 second-order decomposition of nitrogen industrially important 949 acid chlorides 835, 1012, 1028, 1042 dioxide 668–70 IR spectra 889–90 hydrolysis 1032, 1035 activities 355, 523 metal hydride reductions 964–5 reaction with alcohols 1031, 1032 actual yields 98 nomenclature 947 reaction with ammonia and amines acyclic alkanes 58 nucleophilic acyl additions 1027 1036, 1037 acyl groups 1012 oxidation to carboxylic acids 967–8, 1020 acid halides 746 acyl halides 746 See also acid halides from ozonolysis of alkenes 950 formation of 1028 structure and bonding 1012 position of keto–enol equilibrium 969 nomenclature 1016 acylation of aromatic compounds 742, 746–7 preparation from oxidation of alcohols structure and bonding 1012 addition to the carbon–carbon double bond 723 950 adducts 481, 556 reaction to form 2 alcohols 826 acid ionisation constants (pKa) 448 ° alcohols in dilute aqueous solutions 827 drawing structures 483 reaction with addition of Grignard amines 855 adenines 739 reagents 951–5 a-ammonium groups 1067 adenosine diphosphates (ADP) 526, 631, 634 reduction to 1° alcohols 826, 964, 966 aromatic carboxylic acids 1024 adenosine triphosphates (ATP) 526, 31, 634 reductive amination of 962, 964 a-carboxyl groups 1067 amount of glucose in 988 solubility 948, 1018 carboxylic acids 1023–5 chair conformations 991 structural formula 56–7 interpreting 449 adhesive forces 260 structures 944 ionisable groups of amino acids 1067 adiabatic processes 300 alditols 995–6 phenols 839 adipic acids 1014 d-aldohexoses 988 phosphoric acids 623 agricultural chemicals 163 aldopentoses 990 side-chain caryboxyl groups 1067 agricultural fertilisers 622, 633 aldoses 986 acid–base indicators 472 COPYRIGHTEDAir Canada 26 MATERIALaldotetroses 988–9 pKa 479 air pollution and ways to reduce 372 aldotrioses 986, 988 colours of acid and base forms 480 airbags 498 aliphatic aldehydes 949 common 481 airconditioning, working principles behind 331 aliphatic amines 847 how they work 479–80 alanines 858, 1063 nomenclature 848–9 selecting best indicators 480–1 d-alanines 1065 aliphatic carboxylic acids 1012 acid–base reactions 432 Alcoa 605 nomenclature 1014 carboxylic acids 1023–5 alcohols 822–7, 1014 solubility 1018 group 13 620 1H-NMR spectrum 910 aliphatic dicarboxylic acids 1014 phenols 840 acid-catalysed dehydration to alkenes aliphatic hydrocarbons 698 See also alkanes acid–base reactions in water 436–42 831–3 alkadienes 720 acid–base titrations 472–81 acidity of 827 alkali metals 17 amino acids 1068 from addition of Grignard reagents to alkaline batteries 534 glycines 1069 carbonyl compounds 826–7 alkaline earth metals 17 strong acid–strong base 472–4 basicity of 827 alkaline regions weak acid–strong base 474–7 boiling points 948, 1018 strong acid–strong base/strong base–strong weak base–strong acid 474–7 functional groups 822 acid 474 acid–catalysed halogenations 970 IR spectrum 888 weak acid–strong base/weak base–strong acid–catalysed hydrations oxidation to form aldehydes 950 acid 477 aldehydes and ketones 956–8 physical properties 824–5 alkaloids 848 alkenes 728–30 preparation from alkenes 825 alkanes 698–711 aromatic compounds 744 preparation from haloalkanes 826 13C-NMR spectrum 909 mechanisms of additions 729 primary (1°) 823 boiling points 247, 708–9, 824 Index I-1141 BMIndex I-1141 1 June 2015 9:06 AM alkanes (continued) amines 847–53 anti selectivity 731 condensed and molecular formulae 699 1H-NMR spectrum 912 antibodies 1060 conformation 700–1 pKa at 25° 855 antibonding molecular orbitals 206, 208 constitutional isomerism 61–2 pKb at 25° 854–5 antibonding orbitals 265–6 formation from reduction of alkenes 731–2 basicity of 854–7 anti-cancer agents 560 high-molar mass 709 determining class of 848 anti-cancer drugs 781, 1000 IHD 876 IR spectra 889 anticoagulants 1019 IR spectrum 886–7 physical properties 851–2 antifreeze 410 isomeric 709–10 preparation from haloalkanes 852–3 anti-inflammatory drugs 781 NMR spectrum 908–9 reaction of aromatic amines with nitrous antimony 607, 610, 622, 623 nomenclature 58–63, 699, 702–3 acids 859–61 nomenclature 564 physical properties 708–11 reaction to form amides 861 valence electrons 149 reactions of 722–3 reaction with carboxylic acid apatites 266, 608, 635 structures 698, 699 derivatives 1036 aprotic solvents 805, 806, 834 alkanolates 828 reactions with acids 857–61 aqua regia 520 alkenes 698, 711, 1038 separation and purification of 857–8 arenes 698, 711–12, 734 1H-NMR spectrum 909–10 synthesis from carboxylic acids 1039 argentites 486 13C-NMR spectrum 910 synthesis into arylamines 853 argon 618 acid-catalysed dehydration from synthesis by reductive amination 963–4 close-packed structures 277 alcohols 831–3 use in pharmaceuticals 859 phase change data 268 acid-catalysed hydrations 728–30 a-amino acids 1062, 1063 Argyle diamond mine 696 addition of bromine and chlorine 730–3 d-amino acids 1065 aromatic aldehydes 949 addition of hydrogen halides 724–8 amino acids 628, 630, 1060, 1062–74 See also aromatic amines 847 addition to the carbon–carbon double peptides; polypeptides; proteins pKa and pKb at 25° 855 bond 723 pKa 1067 reaction with nitrous acids 859–61 characteristic addition reactions to 723 acidic groups 1066–8 solubility 852 cis–trans configurations 717 analysis based on charge 1073 aromatic carboxylic acids 1012 cis–trans isomers 713 analysis of 1075–6 acidity of 1024 configuration usingE,Z system 719 basic groups 1068 nomenclature 1015 designating configurations 717–19 electrophoresis 1071–3 aromatic compounds 734–42 E,Z systems 718–19 isoelectric points 1070–1 acylation 746–7 electrophilic addition reactions 723–33 in meteorites 1066 alkylation 745–6 IHD 876 other common 1065 bromination 743 IR spectrum 886, 887 pH 1069–70 chlorination 743 low-molar-mass 712, 717 protein-derived 1063–4 electrophilic aromatic substitutions 742–7 nomenclature 716–22 ratios of undissociated acids compared with Friedel–Crafts acylation 949–50 ozonlysis of 950 conjugate base 1070 aromatic dicarboxylic acids 1015 physical properties 722 separation of mixture based on aromatic hydrocarbons 734 See also benzenes preparation into alcohols 825 charges 1073–4 IR spectrum 889 reactions of 723–33 sequence analysis 1076 nomenclature 739–42 reduction to form alkanes 731–2 structural variations 1063 resonance energies 737 relative stabilities 732–3 titration of 1068–9 aromatic ketones 949 shapes of 712–13 4-aminobutanoic acids (GABA) 1065 aromatic properties 734, 738–9 alkoxides 828 b-amino alcohols 955 Hückel’s criteria 738 alkoxy groups 842 amino sugars 989 Arrhenius, Svante 432, 665 alkyl carbocations, order of stability 727 ammonia 184, 350, 482 Arrhenius equation 667–70 alkyl groups 59–60 calculating pH of ion buffers 468 arsanes 622 alkyl halides 724, 792–3 catalytic formation of 681 L-ascorbic acids 997 alkylamines 849 changing equilibrium 368–9 arsenic 610, 622 alkylation of aromatic compounds 742, 745–6 HSAB principle 486 arsenic acids 623 alkylbenzenes 1020 periodic trends in boiling points 251 arsenous acids 623 alkynes 2, 698, 711 phase diagrams 271–2 aryl grignards 952 hydration of 950–1 reaction with carboxylic acid aryl groups 734 IHD 876 derivatives 1036–7 ascorbic acids 478 IR spectrum