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Copyrighted Material INDEX A acidic solutions 468 reaction with phosphorus halides acidity constants (Ka) 478 See also 686–7 absolute temperature 320 Henderson–Hasselbalch equation reaction with thionyl chloride 686 absolute uncertainty in measurements 112 buffer solutions 490–1 solubility 436 absorption spectrum 165 determining 480 structural formulae for various 56–7 acceptor stems 782 values for weak monoprotic acids at aldehydes 683, 690, 691–2, 734 accessible electrons See valence electrons 25 °C 479 condensed structural formula 58–9 accuracy of measurement 109 acidophiles 458–9 aldopentoses 739 acetals 742 acids See also conjugate acids; monoprotic aldoses 734, 737 acetic acid and vapour pressure 291 acids; strong acids; weak acids algebraic equations 84–7 acetone of alcohols 684 aliphatic amines 694, 702–3 boiling point and structure 262–3 amino acids 758 nomenclature 695–6 dipolar forces 262 balancing equations for redox reaction with nitrous acid 708 acetylene 616 reactions 519 aliphatic carboxylic acids 710 acetylsalicylic acid 660 binary 487–8 nomenclature 713–14 achiral molecules 663, 667 Brønsted–Lowry definitions 460–6 aliphatic hydrocarbons 590 See also acid anhydrides 711 commonly found in nature 463 alkanes nomenclature 716 commonly used in laboratories 462 alkadienes 626 acid halides 710 contributing factors to strength 487 alkali metals 25 nomenclature 716 diprotic 464, 774 alkaline batteries 542 acid ionisation constants (pKa) insects’ defence mechanisms 474 alkaline dry cells 542 acidity of αβ-ammoniumχσδλπρ groupsµνγ ε 759 polyprotic 464, 774 alkaline earth metals 25 acids 478–9 reaction with amines 704–8 alkaline regions 495–6 amines 702 redox reactions in 518–20 alkaline solutions 468 amino acids 759 strength of 472–4 alkaloids 705 interpreting 480 strength of amines 702 alkanamines 695 selected alcohols in aqueous triprotic 464 alkanes 590, 591–609 See also saturated solution 684 actinoids 24 hydrocarbons side-chain carboxyl groups 759 activation energies (Ea) 571, 572 balancing combustion reactions 630–2 values for weak monoprotic acids at activators 771 boiling point 261, 603–4, 681 25 °C 479 actual yields 148 conformation 593–5 acid–base indicators 493, 497–9 acyclic alkanes 60 constitutional isomerism 64–6 common 498 acyclovir 780–1 conversion from alkenes 646–7 nature’s own 499–500 acyl groups 710 cycloalkanes 595–603 acid–base reactions 123–4, 460 addition to the carbon–carbon double density 604 alkenes 637 bonds 632 high-molar-mass 604 conjugate acid–base pairs 464–6 adenine 773, 778 identifying parent chain 61 conjugate bases for Brønsted–Lowry adenosine 5′-triphosphate (ATP3-) 774–5 isomeric 604–7 acids 465 adhesive forces 289 IUPAC guidelines 62–4 identifying conjugate acid–base pairs agricultural fertilisers 366, 368 molecular and condensed structural in 465–6 air pollution and equilibrium 394–5 formulae 592 predicting equilibria 701 alanine 707, 762 nomenclature 60–4, 592 acid–base reactions in water 467–74 Fischer projections 756 physical properties of 603–9 autoprotolysis of water 467–9 COPYRIGHTEDalcohols 665, 677–93 MATERIALreactions of 630–2 pH 469–72 acid-catalysed dehydration 687 solubility 681 strength of 472–4 acid-catalysed dehydration to alkanolates 685 acid–base titrations 493–9 alkenes 687–90 alkatrienes 626 acidic region 495 basicity of 684–5 alkenes 590, 609–30 alkaline region 495–6 boiling point and solubility 681 acid-catalysed hydration 640–1 calculating endpoint 496 classifiying 680 addition of bromine and chlorine equivalence points 495 conversion to haloalkanes 685–7 644–5 initial pH 495 ester formation 692–3 alcohol conversion by strong acid–base titrations 494–7 acid ionisation constants (pKa) 684 dehydration 687–90 acid-catalysed dehydration naming guidelines 677–9 characteristics of addition alcohols 687–90 physical properties of 680–1 reactions 632 three-step 689 preparation from alkenes 682 cis–trans isomers 611–12 two-step 689–90 preparation from haloalkanes 682–3 describing cis–trans isomers 617–19 acid-catalysed hydration 640–1 preparation of 682–3 electrophilic addition reactions 633–48 alkenes 682, 687–90 production from reducing carbonyl enthalpy of hydrogenation 646–8 mechanism of 643 compounds 683 isomers 688 acidic natural environments 458 reaction with active metals 685 low-molar-mass 610, 617 acidic regions 495 reaction with hydrohalic acids 685–6 nomenclature 614–17 Index 823 BMIndex 823 4 May 2015 1:16 PM alkenes (continued) ammonia gases, acid–base reactions atomic force microscopes 11 physical properties of 628–9 461–2 atomic mass 19–21 production into alcohol 682 ammonium dichromate 513 calculating averages from isotopic reactions of 632–48 αβ-ammoniumχσδλπρ groupµνγ ε ionisation abundances 21–2 reducing to form alkanes 646–7 constants 759 of isotopes 20 shapes of 611–13 ammonium ion buffers and pH 491–2 ranges and conventional masses 21 specifying configuration usingE,Z amorphous solids 297–8 atomic mass unit (u) 19 system 622–3 amount of substance 132 atomic numbers (Z) 18 stabilities of 646–8 amphiprotic compounds 462 atomic orbitals 157, 174, 181 tri-and tetrasubstituted amplitude 158 hybridisation processes 241–6 configurations 619–20 orbital overlaps 240 atomic radii 199–201 two-step mechanisms in electrophilic amylase, structures 768 trends in 200–1 addition reactions 635–7 amylopectin 745 atomic theories 11–15 vision and colour detection in amylose 745 atomisation enthalpy (∆atH) 341 eyes 612–13 analogous forces 260 atoms 7 ways to designate configuration 617–23 angle strain 597 absorption and emissions spectra 162–4 alkoxides 685 anhydrous 37 colours and sizes to represent 46 alkyl groups, nomenclature, formulae and aniline 696, 706, 707–8 composition 19 abbreviations 61 animal fats 748, 749 counting 136 alkylamines 695 anionic surfactants 436–7 early history 12 alkynes 590, 609 anions 7–8 electrons in 26–7 nomenclature 616–17 anode reactions 542 excited states 163 physical properties of 628–9 anodes 525–7, 538 ground states 163 shapes of 611–13 anomeric carbons 738 and light 162–3 alpha particles 17 anomers 739 lone pairs 38 amides 711–12 anti addition 645 magnetic properties of 196–7 hydrogen bonds 765 anti selectivity 645 spectra 164–6 nomenclature 716–17 antibiotics and resistant strains of structures 15–21 amines 693–709 bacteria 718 Aufbau principle 186, 191, 193 amide formation 708–9 anti-cancer drugs 668 Australian Institute of Sport 308 boiling point and solubility 697–8 anticodon 782 autoionisation of water 467 classifiying 694–5 antisense strands 783 autoprotolysis constant of water preparation from haloalkanes 698–9 antiviral drugs 780–1 (Kw) 467–9 reaction with acids 704–8 apatites 297 at various temperatures 468 reaction with bases 700–4 apoenzymes 769 autoprotolysis of water 467–9 separation and purification of 706 aqueous solutions, electrolysis in 538–40 determining if blood is acidic or strength of bases 703–4 arenes 590, 610, 649 basic 468–9 synthesis of arylamines 699 arginine and basicity 760 Avogadro constant (NA) 132–3, 136, 270 use in pharmacological drugs 705–6 argon, phase changes 300 axial bonds 598, 740 αβ-aminoχσδλ acidsπρ µνγ755ε arithmetic operations 80–4 axial hydrogen atoms 598 αβ-ammoniumχσδλπρ groupµνγ ε ionisation constants additions 81 interconversions 599 (pKa) 759 division and fractions 80–1 axial positions 229 amino acids 755–61 divisions 82 axial–axial interactions 599–600 20 common acids found in multiplications 80, 82 azide ions 699 proteins 756–7 percentages 82–4 azimuthal quantum numbers (l) 174 acid–base properties 758–9 subtractions 81 azo compounds 708 acidic side chains 757 aromatic amines 694, 702–3 assessing structural variations 757–8 base and acid strengths 702 chirality 755 nomenclature, molecular and condensed B acid ionisation constants (pKa) 759 structural formulae 696 balanced chemical equations 126, 128–32 L-amino acids 756 physical properties of 698 combustion of methane 630 non-polar side chains 756 reaction with nitrous acid 707–8 guidelines for 128 polar side chains 757 aromatic carboxylic acids 710 ball-and-stick models amino sugars 738 nomenclature 714 aldehydes and ketones 58 ammonia (NH3) 366, 368 aromatic compounds 648–52 alkanes 591, 593 calculating Kc from equilibrium drawing resonance structures 652–3 ammonia 227 concentrations 403–5 resonance strengths 652 butan-2-ol 665 derivatives 693 aromatic dicarboxylic acids, chlorine pentafluoride 231, 232 equilibrium constant expression nomenclature 714 chlorine trifluoride 230 (Kc) 381–2 aromatics 589 cyclohexane 598 formation of 556 Arrhenius, Svante 460, 571 methane 45, 227 phase diagrams 304–5 Arrhenius equation 573 methanol 677 tetrahedral geometry 227 aryl groups 649 napthalene 293 various representations of 47 aspirin 660 See also acetylsalicylic acid phosphorus pentachloride 229, 230 824 Index BMIndex 824 4 May 2015 1:16 PM propane 46 blood sugar 737 burettes 493 sulfur hexafluoride 231, 232 boat conformations 598–9 butan-1-ol sulfur tetrafluoride 229, 230 conversion from chair boiling point 681 triiodide ion 230 conformations 599 nomenclature 678 water 227 Bohr, Niels 166–7 butan-2-ol 665–6 xenon tetrafluoride 232 boiling point elevation (∆Tb) 448 nomenclature 678 Balmer, Johann 166 boiling points See also normal boiling points representations of 668–9 band (metallic solids) 296 alcohols 681 superimposed mirror images 666 barometers 268 alkanes 603–4, 681 butane 64, 127, 662 base ionisation constants (pKb) amines 697–8 boiling point 262–3 amines 702 effect of atmospheric pressure on 291 combustion 123, 126 bases 478–9 increasing
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