http://www.elsolucionario.net LIBROS UNIVERISTARIOS Y SOLUCIONARIOS DE MUCHOS DE ESTOS LIBROS LOS SOLUCIONARIOS CONTIENEN TODOS LOS EJERCICIOS DEL LIBRO RESUELTOS Y EXPLICADOS DE FORMA CLARA VISITANOS PARA DESARGALOS GRATIS hein_FM_i-xxvi_hr1.qxd 11/15/10 3:27 PM Page i INTRODUCTION TO GENERAL, ORGANIC, AND BIOCHEMISTRY Tenth Edition This page intentionally left blank hein_FM_i-xxvi_hr1.qxd 11/16/10 3:43 PM Page iii INTRODUCTION TO GENERAL, ORGANIC, AND BIOCHEMISTRY Tenth Edition Morris Hein Mount San Antonio College Scott Pattison Ball State University Susan Arena University of Illinois, Urbana-Champaign John Wiley & Sons, Inc hein_FM_i-xxvi_hr1.qxd 11/15/10 3:27 PM Page iv Vice President & Executive Publisher Associate Publisher Acquisitions Editor Editorial Project Coordinator Associate Editor Marketing Manager Production Manager Production Editor Cover Designer Executive Media Editor Media Editor Photo Department Manager Photo Editor Senior Illustration Editor Production Management Services Kaye Pace Petra Recter Nicholas Ferrari Catherine Donovan Alyson Rentrop Kristine Ruff Dorothy Sinclair Sandra Dumas Wendy Lai Thomas Kulesa Marc Wezdecki Hilary Newman Ellinor Wagner Anna Melhorn Ingrao Associates This book was typeset in 10/12 Minister Light at Prepare and printed and bound by R R Donnelley (Jefferson City) The cover was printed by R R Donnelley (Jefferson City) Founded in 1807, John Wiley & Sons, Inc has been a valued source of knowledge and understanding for more than 200 years, helping people around the world meet their needs and fulfill their aspirations Our company is built on a foundation of principles that include responsibility to the communities we serve and where we live and work In 2008, we launched a Corporate Citizenship Initiative, a global effort to address the environmental, social, economic, and ethical challenges we face in our business Among the issues we are addressing are carbon impact, paper specifications and procurement, ethical conduct within our business and among our vendors, and community and charitable support For more information, please visit our website: www.wiley.com/go/citizenship The paper in this book was manufactured by a mill whose forest management programs include sustained yield -harvesting of its timberlands Sustained yield harvesting principles ensure that the number of trees cut each year does not exceed the amount of new growth This book is printed on acid-free paper q Copyright © 2012, 2009, 2005, 2001 by John Wiley & Sons, Inc All rights reserved No part of this publication may be reproduced, stored in a retrieval system or transmitted in any form or by any means, electronic, mechanical, photocopying recording, scanning or otherwise, except as permitted under Sections 107 or 108 of the 1976 United States Copyright Act, without either the prior written permission of the Publisher or authorization through payment of the appropriate per-copy fee to the Copyright Clearance Center, 222 Rosewood Drive, Danvers, MA 01923, (978) 750-8400, fax (978) 646-8600 Requests to the Publisher for permission should be addressed to the Permissions Department, John Wiley & Sons, Inc., 111 River Street, Hoboken, NJ 07030-5774, (201) 748-6011, fax (201) 748-6008 Evaluation copies are provided to qualified academics and professionals for review purposes only, for use in their courses during the next academic year These copies are licensed and may not be sold or transferred to a third party Upon completion of the review period, please return the evaluation copy to Wiley Return instructions and a free of charge return shipping label are available at www.wiley.com/go/returnlabel Outside of the United States, please contact your local representative ISBN 13 ISBN 13 978-0470-59880-1 978-0470-91774-9 Printed in the United States of America 10 hein_FM_i-xxvi_hr1.qxd 11/15/10 3:27 PM Page v We dedicate this edition to The International Year of Chemistry 2011 This page intentionally left blank hein_FM_i-xxvi_hr1.qxd 11/15/10 3:27 PM Page vii ABOUT THE AUTHORS Morris Hein is professor emeritus of chemistry at Mt San Antonio College, where he regularly taught the preparatory chemistry course and organic chemistry He is the original author of Foundations of College Chemistry and his name has become synonymous with clarity, meticulous accuracy, and a step-by-step approach that students can follow Over the years, more than three million students have learned chemistry using a text by Morris Hein In addition to Introduction to General, Organic and Biochemistry, 10E, he is co-author of Foundations of College Chemistry, 13E He is also the co-author of Foundations of Chemistry in the Laboratory, 13E and Introduction to General, Organic and Biochemistry in the Laboratory, 10E Scott E Pattison lives in Muncie, Indiana, where he is a professor of chemistry at Ball State University He maintains active, current research involving zinc metabolism that provides laboratory experience for both undergraduate and graduate students A dedicated teacher at the university level for twenty-seven years, his primary area of instruction is biochemistry; however, he greatly enjoys teaching medical/nursing chemistry and general chemistry Scott became a co-author with Morris Hein on the third edition of Introduction to General, Organic, and Biochemistry, and he brings his knowledge of students, subject matter, and current research to the text In addition to his professional career, he volunteers in local schools from preschool through high school, providing extra science experiences for tomorrow’s university students Susan Arena has taught chemistry to students at many levels including middle school, high school, community college and most recently at University of Illinois, Urbana-Champaign She especially focuses on using active learning techniques to improve the understanding of concepts in chemistry Susan currently authors chemistry texts and electronic media, and presents workshops for teachers in using active learning and electronic media to teach chemistry She collaborated with Morris Hein on the seventh edition of Foundations of College Chemistry and became a co-author on the eighth and subsequent editions We remember Leo R Best, our colleague, who was an original co-author of this book with Morris Hein vii This page intentionally left blank hein_index_I1-I18hr1.qxd 11/15/10 1:28 PM Page I-8 I-8 INDEX Food irradiation, 452 Food processing, enzymes and, 839 Formaldehyde, 134, 604, 619–620 Formamide, 673 Formic acid, 636, 637 Formulas equation, 368 percent composition from, 130–131 writing from ionic compound names, 105–106 Fossil fuels, 160–162, 472–473 Foul odors, 592, 681 Free amino acids, 818–819 Free-radical mechanism for alkane halogenation, 489–491 Freezing point depression constants, 333–335 Freezing points, 32, 296–297 Freons, 280 Frequency, waves and, 195 Fructofuranose, 739 Fructose, 730, 738–739, 744 Fumaric acid, 641 Functional groups, 471, 566 Furanose ring, 739 Fused aromatic ring systems, 535–536 Fusion reactions, 456–457 G Galactocerebrosides, 774 Galactose, 730, 738–739, 748 Galactosemia, 730 Gamma rays, 442, 446–447 Gangliosides, 774 Gas formation, 155 Gas stoichiometry, 275–279 mass-volume calculations, 275–277 mole-volume calculations, 275–277 volume-volume calculations, 277–278 Gaseous elements, 45 Gases Avogadro’s law and, 269–270 Boyle’s law and, 257–260 Charles’ law and, 260–263 combined gas laws, 264–266 common materials in, Dalton’s law of partial pressures, 267–269 density of, 35, 270–271 diffusion and, 253 effusion and, 253 gas stoichiometry, 275–279 Gay-Lussac’s law and, 263–264 general properties of, 252 ideal gas, 252, 270–271 kinetic-molecular theory and, 252–253 mole-mass-volume relationships of, 270–271 physical properties of, pressure measurement, 254–255 pressure of, 255–256 real gases, 279–282 solubility in water, 321 standard conditions and, 264–265 temperature and, 261 Gasoline, 491–494 combustion, 67 hydrocarbons and, 492 octane numbers and, 492 reformulated, 493–494 renewable fuel and, 493 Gastric digestion, 909 Gastric juices, 909 Gastric lipase, 909 Gastrin, 955 Gastronomy, molecular, 3–4 Gay-Lussac, J L., 263 Gay-Lussac’s law, 263–264, 269–270 Geiger counter, 450 Geiger-Müller detecting tube, 450 Genes cancer and, 872–873 genetic code, 871–872 genetic control, 870–871 genetic diseases, 874 Human Genome Project, 873–874 mutations and genetic engineering, 877–879 oncogenes, 872 tumor-suppressor genes, 872–873 Genetic code, 871–872 Genetic control, 870–871 Genetic diseases, 874 Genetic effects, radiation and, 460 Genetic engineering, 797, 877–879 Genetic transcription, 867–871 Genome, 864 Geometric isomerism in alkenes, 511–517 in polymers, 557–558 Ginger, 839 Glassware, volume measurements and, 30 Global warming, 160–162, 281 Globular proteins, 809–817 carboxypeptidase A, 812–813 fatty acid proteins, 813 ferritin, 813 hemoglobin, 810–812 HIV reverse transcriptase, 813 human growth hormone, 814 immunoglobulin G, 815–817 myoglobin, 810 myosin, 814 Glucagon, 955, 956 Glucogenic amino acids, 977 Glucokinase, 837 Gluconeogenesis, 945, 952–953 Glucopyranose, 735–736, 738 Glucopyranoside, 738 Glucose, 134 aldehyde groups and, 748 catabolic pathways and, 944–945 catabolic process and, 940 concentrations, 956 conversion to pyruvate, 946 glucose oxidase test, 749 glucose tests, 749 glucose-tolerance test, 957 importance of, 729–730 invert sugar and, 744 liver function and, 911 metabolic energy and, 942–943 metabolism, 837 monitoring kits, 749 monitors, 957 mutarotation and, 734–737 polysaccharides derived from, 750–754 storage of, 945 structure of, 731–735 water solubility of, 572 Glutamic acid-lysine ionic bonding, 806 Glutamic acid-tyrosine hydrogen bonding, 806 Glutamic acids, 797 Glutaric acid, 642 Glutaric anhydride, 642 Glycemic index, 726 Glyceraldehyde, 734 Glyceride hydrogenation, 656 Glycerol, 583, 653 Glycerol esters, 654–657 glyceride hydrogenation, 656 hydrogenolysis and, 656 hydrolysis and, 656–657 saponification and, 657 types of, 654–655 Glyceryl tripalmitate, 657 Glycine, 797 Glycogen, 751 Glycogen-storage diseases, 945 Glycogenesis, 945 Glycogenolysis, 945 Glycolipids, 765, 774 Glycolysis, 642, 930, 947, 949 Glycosaminoglycans, 755 Glycosides, 738 Glycosidic linkage, 738 Glycosis, 746 Glycosuria, 730 Glycylalanine, 801 Glycylglycine, 800 Gold, 68 Golden rice, 879 Goldstein, Eugen, 86 Goodyear, Charles, 556 Gore-Tex, 489 Graham, Thomas, 253 Graham’s law of effusion, 253 Grape sugar, 729–730 Graphene, 536 hein_index_I1-I18hr1.qxd 11/15/10 1:28 PM Page I-9 INDEX Gray, Theodore, 204 Green algae, 934 Greenhouse, photosynthesis and, 934 Greenhouse effect, 160–162 Ground state, energy levels and, 197 Groups, periodic table and, 204 Growth factors, 801 Growth hormone, 955 Guanine, 853 Guanosine, 854 Guanosine monophosphate, 855 Guayule, 491 Gunpowder, 754 H Haber, Fritz, 388 Haber process, 388 Hahn, Otto, 451 Hair waves, 807 Half-life, 443 Halogenation, 486, 537 Halogens, 48, 204 Halothane, 488 Haworth formulas, 734–736, 739, 742 Hazardous waste disposal, 310 Heart attack, 840 Heartbeats, 856 Heat in chemical reactions, 157–160 of fusion, 297 heating curves, 297 qualitative measurement and, 68–70 of reaction, 159 of vaporization, 297 Helium, 45, 201 Hemiacetals, 613–614, 737–738 Hemiketals, 613–614 Hemoglobin, 810–812 Heptane, 492 Heredity, 864 Heterocycles, 852–853 Heterocyclic compounds, 680 Heterocyclics, 681 Heterogenous matter, Heterogenous mixtures, Hexane, 495 Hexokinase, 837, 841, 843, 846 Hexylresorcinol, 587 High-density lipoproteins (HDL), 777–778 High-energy nucleotides, 855–857 High-energy phosphate bonds, 926–929 High fat diets, energy levels and, 969 High-fructose syrups, 745, 839 Hippuric acid, 966 Histamine, 797 Histidine, 797 HIV reverse transcriptase, 813 Holoenzymes, 833 Homeostasis, 956 Homogenous matter, 8–9 Homogenous mixtures, Homologous series, 473 Hormones blood glucose and, 956 functions of, 953–955 structure of, 955 Hot packs, 322 Hot paraffin wax dip, 473 Hot springs, 949 Human body, mass percent of elements in, 46 Human digestion, 907–910 absorption and, 911 digestive fluids, 900 digestive tract illustration, 908 gastric digestion, 909 intestinal digestion, 909–910 liver function and, 911–912 salivary digestion, 908–909 sequence of, 907–908 Human genome, 866 Human Genome Project, 873–874 Human growth hormone, 814 Hummingbird, 967 Huntington’s disease, 870 Hydrates, 301–303 Hydration, 967 Hydration of a double bond, 967 Hydrazine, 134 Hydrocarbons classes of, 472–473 combustion, 485 fossil fuels and, 158 gasoline and, 492 monochlorination of, 490 names and formulas for, 72 Hydrochloric acid, 109, 426 Hydrochloride salt, 684 Hydrogen bonds, 298–301 empirical and molecular formulas, 134 energy release and, 71 isotopes of, 90 molecule, formation of, 226 number of neutrons in, 93 Hydrogen atom Bohr model of, 197 line spectrum of, 197 modern concept of, 200 orbitals for, 198 principle energy levels in, 198 Hydrogen carbonate-carbonic acid buffer, 403 Hydrogen chloride, 109, 134, 521–522, 527 Hydrogen compounds, 299 Hydrogen cyanide, 615–616 Hydrogen fuel cells, 54 Hydrogen peroxide, 83, 153, 925 I-9 Hydrogenation, glyceride, 656 Hydrogenolysis, 656 Hydrolases, 834 Hydrolysis, 401 amides, 674–675 cellulose, 752 starch, 751 triacylglycerols, 656–657 Hydronium ion, 353 Hydrophilic groups, 657–658 Hydrophobic groups, 658 Hydrophobic lipids and biology, 776–781 Hydrophobic molecules, 764–765 Hydroquinone, 584 Hydroxides, amphoteric, 356 Hydroxy acids, 642 Hydroxy radical, 926 Hydroxyl functional group utility, 578–579 Hydroxyl groups, 566, 579 See also Alcohols Hyperglycemia, 956 Hypoglycemia, 944, 945, 956–957 Hypothesis, scientific method and, I Ice, specific heat of, 68 Ice and water in equilibrium, 303–304 Ice cream, 337 Ideal gas, 252, 273–274 Immiscible liquids, 318–319 Immunoglobulin G, 815–817 Incomplete proteins, 797 Induced-fit model, 842 Induced radioactivity, 450 Industrial dumps, 310 Industrial-strength enzymes, 838–840 Initiation of polypeptide synthesis, 875 Inner transition elements, 206 Inorganic compounds common and systematic names and, 99 elements and ions, 99–103 ionic compound formulas and, 103–104 naming acids, 112–113 naming binary compounds, 105–110 naming compounds containing polyatomic ions, 111–112 Insoluble fiber, 895 Insoluble precipitate formation, 155 Insulin amino acid sequence for, 806 deficiencies in, 804 glucose concentration and, 956 glucose metabolism and, 944 principal functions of, 955 Insulin-like growth factor, 801 Integral membrane protein, 781 hein_index_I1-I18hr1.qxd 11/15/10 1:28 PM Page I-10 I-10 INDEX Intermolecular bonds, 299 International System (SI), 21–23 International Union of Pure and Applied Chemistry (IUPAC), 99 Intestinal digestion, 909–910 Intestinal juice, 909 Intramolecular dehydration alkenes and, 577 ethers and, 578 Inverse PV relationship of gas, 257 Invert sugar, 744–745 Invertase, 730 Iodine, 134, 900 Ion product constant for water, 393–395 Ionic bonds, 218–224 Ionic compounds characteristics of, 52–53 predicting formulas of, 224–225 writing formulas from, 103–104 Ionic-electron method for balancing oxidation-reduction reactions, 419–420 Ionic equations, writing, 368–369 Ionic redox equations, balancing, 419–423 Ionization constants, 395–397 Ionization energy, 216–217 Ionization of water, 362–363 Ionizing radiation, 450, 458 Ions anions, 102 cations, 102 discovery of, 84–85 ion exchange, 308 ionic bond formation, 228–229 ionic radii, 229 metals and nonmetals and, 229 oxidation numbers for, 412 periodic table and, 103 predicting charge on, 102 production of, 100 Iron human deficiency and, 900–901 mixture with sulfur, number of neutrons in, 93 specific heat of, 68 Isobutane, 475–476 Isoelectric focusing, 821 Isoelectric points, 799 Isomaltose, 744 Isomerases, 834 Isomeric phthalic acids, 642 Isomerism, 475–478, 476, 701 Isomerization, 486 Isomers, 476 Isooctane, 492 Isoprene, 555 Isopropanol, 582 Isopropyl alcohol, 582 Isotope detectives, 91 Isotopes of elements, 89–90 Isotopic notation, 90, 443 IUPAC System, 478–481 J Jaundice, 810 Joliot-Curie, Frederic, 450 Joliot-Curie, Irene, 450 Joules, heat measurement and, 68 K Keiffer, Susan W., 33 Kekulé, August, 528 Kekulé structures, 528–530 Kelvin scale, 30–32 Ketals, 613 Ketoacidosis, 973 Ketogenic amino acids, 977 Ketohexose, 730 Ketones addition reactions and, 613–614 aldol condensation and, 616–619 binding and physical properties, 607–610 boiling points of, 608 catalytic reduction of, 580 chemical properties of, 610–619 common, 619–621 formation, 579 hydrogen cyanide addition and, 615–616 ketone bodies, 971–973 naming of, 603–606 oxidation and, 610–612 reduction and, 612–613 structure of, 603 Ketosis, 610, 613, 973 Kevlar, 238 Kiliani, Heinrich, 733 Kiliani-Fischer synthesis, 733–734 Kilograms, 27, 31 Kinetic energy, 67 Kinetic-molecular theory, 252–253 Knocking, 492 Knockout mice, 879 Knoop, Franz, 965 Krebs, Hans A., 950 Krebs cycle, 950–953 Kurti, Nicholas, Kwashiorkor, 897 L L-amino acids, 798 L-glutamine, 978 L-serine, 711 Lactase, 839 Lactic acid, 613, 642, 704, 707–709, 712 Lactic acid buildup, 944 Lactic acidosis, 944 Lactose, 741, 742, 744, 749 Lactose intolerance, 741, 839 Laetrile, 616 Lanthanide series, 206 Lauric acid, 637, 764 Lavoisier, Antoine, Law of conservation of energy, 71 Law of conservation of mass, 66 Law of definite composition, 83 Law of multiple proportions, 83 Lawrence, E O., 449 Le Bel, J A., 703 Le Châtelier, Henri, 384 Le Châtelier’s principle, 384–385, 402 Lead, 68 Lead storage battery cells, 429–430 Lecithins, 772 Legume root nodules, 974 Length measurements, 22–23 Leu-enkephalin, 802 Levodopa, 639 Levorotatory molecules, 706 Levorotatory substances, 703 Levulose, 730 Lewis, Gilbert, 217, 354 Lewis acids and bases, 354 Lewis structures of atoms, 217–218 carbon atom and, 468–469 complex, 235–236 of compounds, 231–235 formulas of, 225 writing of, 232 Liberty Bell, 92 Ligases, 834 Light, electromagnetic radiation and, 195–196 Light absorption, 515 Light reactions, photosynthesis and, 934–935 Light sticks, 390 Lightning flashes, 974 Limiting reactant calculations, 177–182 Lind, James, 892 Line spectrum, 196–197 Line structures, 469–471 Linear molecular structure, 239 Linoleic acid, 764, 766 Linolenic acid, 764 Liothyronine, 955 Lipases, 838–839, 909 Lipids See also Compound lipids; Simple lipids atherosclerosis and, 777–779 bilayers, 780–781 biological membranes and, 779–781 classification of, 765 compound lipids, 765, 771–774 fats in metabolism, 770–771 hydrophobic lipids and biology, 776–781 hydrophobic molecules and, 764–765 hein_index_I1-I18hr1.qxd 11/15/10 1:28 PM Page I-11 INDEX miscellaneous lipids, 765 naturally occurring fatty acids and, 764 simple lipids, 765–770 steroids, 765, 775–776 Lipmann, Fritz A., 950 Lipogenesis, 969–971 Liposomes, 777 Lipoxygenase, 767 Liquid crystalline display, 702 Liquid crystals, 238 Liquid elements, 45 Liquid salts, 684 Liquids boiling point and, 294–296 calibrated glassware in measuring, 30 capillary action and, 294 changes of state and, 297 characteristics of, 291 common materials in, densities of, 35 distillation of, 308 evaporation and, 291–292 freezing point and, 296–297 heat of fusion and, 297 heat of vaporization and, 297 hydrates, 301–303 hydrogen bond and, 298–301 melting point and, 296–297 meniscus curves and, 294 physical properties of, surface tension and, 293–294 vapor pressure and, 292–293 water as unique liquid, 303–307 water purification, 307–308 Lister, Joseph, 587 Liters, 29 Lithium, 202 Lithium aluminum hydride, 612 Liver carbohydrate metabolism and, 943–944 digestion and, 910 energy metabolism and, 964–965 functioning of, 911–912 Livestock feed, 796 Local hormones, 768 Lock-and-key hypothesis, 842 Logarithms, 364 Long-distance running, 953 Long-term radiation damage, 460 Longevity, diet and, 905 Low carbohydrate diets, 972 Low-density lipoproteins (LDL), 777 Lowry, T M., 352 Lowry assay, 819 Lucite, 615 Lung embolisms, 840 Lungs, carbohydrate metabolism and, 943–944 Lyases, 834 Lysine, 797 M MacLeod, J J., 957 Macromolecules, 548 Macronutrients, 891 Magnesium atomic structure of, 201–202 combustion of, 159 human deficiency and, 900 mass of, 92 precipitation and, 308 Magnesium oxide formation, 223 Malic acid, 642 Malonic acid, 641 Maltase, 833–834, 842 Maltose, 741–742, 744, 749 Maltose hydrolysis, 842 Manganese, 900 Manufacturing plant energetics, 919–920 Marasmus, 894 Margarines, 778 Marijuana, 585, 586 Markovnikov’s rule, 522 Mass conservation, 66 Mass defect, 457 Mass-energy relationship in nuclear reactions, 457 Mass-mass calculations, 176–177 Mass measurements, 27–29 Mass number, 90 Mass percent, 129, 325–327 Mass spectrometer readings, 91–92 Mass-volume calculations, 275–277 Mass/volume percent, 327 Masses of equal volumes, 35 Matter classification of, 8–9 particulate nature of, physical states of, 6–7 three states of, 291 McArdle disease, 945 McMillan, Edwin M., 458 Measurement, 13–17 Mechanism of a reaction, 489 Medical uses, enzymes and, 840 Meiosis, 866 Meitner, Lise, 101 Melting point, liquids, 296–297 Membrane lipids, 780 Membranes, biological, 779–781 Mendel, Gregor, 862, 864 Mendelev, Dimitri, 204 Meniscus, 294 Menten, Maud, 8336 Menthol, 576 I-11 Mercaptans, 592 Mercury droplets, 293 liquidity at room temperature, 45 meniscus of, 294 Meso compounds, 715–716 Meso structures, 715–716 Messenger molecules, 268 Messenger RNA (mRNA), 868–869, 872, 874–876 Met-enkephalin, 802 Meta disubstituted compounds, 531 Metabolic acidosis, 639 Metabolic energy changes, 953–954 Metabolic energy sources, 964–965 Metabolic nitrogen balance, 975–976 Metabolic pathways, 940–941 Metabolism cell structure and, 920 molecular oxygen and, 925–926 Metal corrosion, 365 Metal oxides acids reaction with, 355 plus acid, 155 water reactions with, 306–307 Metaldehyde, 620 Metalloids, 50 Metals acids reaction with, 355 activity series of, 423–425 atomic radii of, 221 electroplating of, 427 ionization energies and, 216–217 periodic table and, 49 periodic trends in, 214 water reactions with, 305–306 Methadone, 688 Methamphetamine, 686 Methanal, 604, 619–620 Methane in atmosphere, 161–162 ball-and-stick model of, 239 boiling point of, 571 characteristics of, 473 chlorination products of, 487 geometric shape of, 237 model illustrating, 476 volume-temperature relationship for, 260–261 Methanethiol, 592 Methanol, 580–581, 592 Methemoglobin, 680 Methionine, 797 Methyl butyrate, 652 Methyl ethyl ketone, 606, 620–621 Methyl methacrylate, 615 Methylamine, 681, 683 Methylammonium chloride, 684 Methylpentane, 481 Methylphenols, 585 hein_index_I1-I18hr1.qxd 11/15/10 1:28 PM Page I-12 I-12 INDEX Metric system, 21–23 common prefixes and numerical values, 21–22 length measurements, 22–23 standard units of measurement, 22 units of mass, 28 Meyer, Lothar, 204 Micelles, 777 Michaelis, Leonor, 8336 Michaelis-Menten plot, 836–837 Micro RNA (mRNA), 871 Microbial chemical warfare, 618 Microbots, 178 Microchip technology, 178 Microchips, 549 Micromachinery, 178 Micronutrients, 891 Microvilli, 911 Miescher, Friedrich, 864 Milk sugar, 741 Minerals, 900–901 Miscible liquids, 318 Mitochondria, 923 Mitochondrial ATP synthetase, 816 Mitochondrial electron transport, 930 Mitochondrion photomicrograph, 926 Mitosis, 866 Modern atomic theory atomic structures of first eighteen elements, 200–203 Bohr atom and, 196–198 brief history and, 195 electromagnetic radiation and, 195–196 electron energy levels and, 198–200 Pauli exclusion principle and, 199 Molar mass of compounds, 126–129 definition of, 169 determination of, 123–124 Molar volume, 270–271 Molarity, 327–329, 335 Mole, 122–124 Mole-mass calculations, 174–175 Mole-mass-volume relationships of gases, 270–271 Mole-mole calculations, 171–174 Mole ratio, 170 Mole relationship with molecules, 169 Mole-volume calculations, 275–277 Molecular accelerators, 833 Molecular compounds, 52–53 Molecular formulas, 469–471 calculating from empirical formula, 137–138 empirical formula compared, 132–133 Molecular gastronomy, 3–4 Molecular machines, 816 Molecular models, 469–471 Molecular oxygen and metabolism, 925–926 Molecular shape, 237 determining using VESPR, 240 electron pair arrangement and, 241 linear structure, 239 tetrahedral structure, 239–240 trigonal planar structure, 239 Molecules compounds and, 52 dependence of pressure on, 255–256 messenger molecules, 268 relationship with mole, 169 Molybdenum, 900 Monochlorination of hydrocarbons, 490 Monomers, 548 Monoprotic acid, 638 Monosaccharides, 729–730 classification of, 726 fructose, 730 galactose, 730 glucose, 729–730 oxidation and, 747 redox reactions of, 746–750 reduction and, 747–748 Monosodium glutamate (MSG), 643, 976 Monosubstituted benzenes, 530–531 Monosubstitution, 487 Movement proteins, 814 Mucopolysaccharides, 755 Multiplication, significant figures in, 18–19 Municipal water-treatment plants, 307 Muscle contractions, 931–933 Muscle mass, maintaining, 933 Muscle movements, 856 Muscle proteins, 808 Muscle rubs, 608 Muscles, striated, 931 Muscone, 609 Mutagen, 877 Mutarotation of glucose, 734–737 Mutations, 877–879 Mylar, 583, 652 Myocardial infarction, 952 Myoglobin, 810 Myosin, 814 Myosin protein, muscle contractions and, 931–933 MyPyramid, 905 Myristic acid, 637, 764 N N-substituted primary amines, 678 N-terminal residue, 800 NADH, 948–949 Nanorobots, 178 Nanotechnology, 816 Natta, Giulio, 557 Natural gas, 72, 473 Natural law, 83 “Natural” plastics, 651 Natural radioactivity, 443–445 Natural rubber, 555, 557 Natural states, elements in, 50 Naturally occurring fatty acids, 764 Negative nitrogen balance, 976 Neon, 202 Neotame, 745–746 Net ionic equations, 368–369 Neuropeptide FF, 802 Neuropeptide Y, 802 Neurotensin, 802 Neurotransmitters, 268, 797 Neutralization, 355, 366–367 Neutrons characteristics of, 86 determination of in atoms, 93 electrical charge of, 87 relative mass of, 87 Niacin, 899 Nickel, 900 Nicotinamide adenine dinucleotide (NAD), 923–924 Nicotinamide adenine dinucleotide phosphate (NADP), 923–924 Nicotine, 687 Nifedipine, 617–618 Ninhydrin test, 819 Nitration, aromatic hydrocarbons and, 537 Nitrile hydrolysis, 646 Nitriles, reduction of, 682 Nitro compounds, 682 Nitrogen, 134, 202 balance, 976 excretion of, 978–981 fixation, 973–975 gases, 50 nitrogen-containing heterocyclics, 681 nitrogen cycle, 973–975 nitrogen-fixing microorganisms, 974–975 transfer, amino acids and, 977–978 Nitrogen monoxide, 268, 282 Noble gases, 48, 204, 218 Noble metals, 50 Noncovalent bonds, 807 Nonelectrolytes, 357–358 Nonionic detergents, 659 Nonmetal oxides, water reactions with, 306–307 Nonmetals atomic radii of, 221 ionization energies and, 216–217 periodic table and, 49–50 periodic trends in, 214 water reactions with, 305–306 Nonpolar amino acids, 795 Nonpolar covalent bonds, 228–230 Nonsense codons, 871 hein_index_I1-I18hr1.qxd 11/15/10 1:28 PM Page I-13 INDEX Nonsteroidal anti-inflammatory drugs (NSAIDs), 768 Norepinephrine, 686 Normal boiling point, 294–295 Normal butane, 476 Nuclear atom, 87–89 Nuclear binding energy, 457 Nuclear chemistry acute radiation damage, 458–460 alpha particles, 445–446 artificial radioactivity, 450 atomic bomb, 455–456 beta particles, 446 gamma rays, 446–447 genetic effects of radiation, 460 isotopic notation and, 443 long-term radiation damage, 460 mass-energy relationship, 457 natural radioactivity, 443–445 nuclear fission, 451–453 nuclear fusion, 456–457 nuclear power, 453–455 radioactive disintegration series, 448–449 radioactivity discovery, 442–443 radioactivity measurement, 450–451 transmutation of elements, 449–450 transuranium elements, 458 Nuclear fission, 451–453 Nuclear fusion, 456–457 Nuclear power, 453–455 Nuclear power plants, 454–455 Nuclear radiation characteristics, 448 Nuclear scanning, 459 Nuclear waste, 455 Nucleic acids See also Deoxyribonucleic acid; Ribonucleic acid bases and nucleosides, 852–854 defined, 852 high-energy nucleotides, 856–857 nucleosides, 855–856 polynucleotides, 857–859 Nucleons, 443 Nucleoproteins, 852 Nucleotide guanosine-5’-triphosphate (GTP), 875 Nucleotides, 855–857 Nucleus, atom, 89 Nuclides, 443 Nutrition See also Human digestion absorption process and, 911 amino acids and, 897 balanced diet, 904–907 calorie deficiency and, 894 carbohydrates and, 894–896 content labeling, 901–903 diet and, 892–899 diet and longevity, 905 energy and, 892–894 establishing dietary needs, 892 fats and, 896 fiber and, 895 food additives and, 903–904 food coloring and, 903–904 macronutrients, 891 micronutrients, 891 minerals and, 900–901 nutrients, 891 nutrition content labeling, 901–903 obesity and, 894 proteins and, 897 restricted calorie diets, 894 sucrose content and, 895–896 vegetarian diets, 897 vitamins and, 897–899 water and, 901 Nutrition Facts, 901–903 Nylon, 549, 676 O Obesity, 894 Observations, Octane, 175 Octane number, 492 Octane rating, 492 Octanoic acid, 638 Oils, 654–655 Old Faithful, 33 Oleic acid, 764 Oligosaccharides, 726 Olive oil, 777 Omega-3 fatty acids, 767–768 Omega-6 fatty acids, 767–768 Oncogenes, 872 atmosphere (atm), 255 Opiates, 688 Optical activity, 703 Orbitals, 198–199 atomic orbitals, 198 d orbitals, 199–200 diagrams, 201, 203 orbital filling, 203 p orbitals, 199–200 Pauli exclusion principle and, 199 s orbitals, 199–200 spin and, 198–199 Orexin, 802 Organ cooperation, carbohydrate metabolism and, 942–943 Organelles, 921 Organic chemistry alkane reactions, 485–491 alkane sources, 491 alkanes, 473–478 carbon atom and, 468–469 carbon reactions, 484–485 cycloalkanes and, 494–497 gasoline and, 491–494 history and scope, 467–468 hydrocarbons and, 472–473 naming organic compounds, 478–483 I-13 organic compound classification, 470–472 organic formulas and molecular models, 469–471 Organic compounds classification of, 470–472 naming of, 478–483 Organic formulas, 469–471 Organic peroxides, 552 Orlon, 527 Osmosis, 338–339 Osmotic pressure, 338–339 Osteoarthritis, 755 Oxalic acid, 640–641 Oxidation alcohols and, 573–576 aldehydes and ketones and, 610–612, 644–645 alkenes and, 524–525 fatty acids and, 965–969 monosaccharides and, 747 oxidation number, 412–414 oxidation state, 412 oxidative phosphorylation, 929–931, 950 oxidative stress, 926 oxidized fats, 525 primary alcohol and, 644–645 Oxidation-reduction, 921–925 activity series of metals, 423–425 balancing equations, 416–419 balancing ionic redox equations, 419–423 carbon and, 484 electrolytic and voltaic cells, 425–430 oxidation number and, 412–414, 416 oxidizing agents, 415 reducing agents, 415 Oxides, 225 Oxido-reductases, 834 Oxonium ion, 573 Oxy-acids, 111, 113 Oxy-anions of chlorine, 111 Oxygen atomic structure and, 202 carbon dioxide exchange in blood, 402 collected over water, 267 electronegativity and, 305 empirical and molecular formulas, 134 gases, 50 hydrogen bonding and, 299 number of neutrons in, 93 percent of atmosphere, 45 reviving damaged art and, 50 Oxytocin, 802–803, 955 Ozone, 280–281 Ozone layer, 280 hein_index_I1-I18hr1.qxd 11/15/10 1:28 PM Page I-14 I-14 INDEX P Palmitic acid, 637, 764, 965 Palmitoleic acid, 764 Pancreatic amylases, 910 Pancreatic juice, 909 Pancreatic lipases, 910 Pantothenic acid, 950 Paper pulp, 840 Para disubstituted compounds, 531 Paraffins See Alkanes Paraldehyde, 620 Parathyroid hormone, 955 Parkinson’s disease, 639, 797 Parrots, fluorescence and, 196 Partial pressures, 267–269 Particle size, solid dissolving rate and, 323 Particulate nature of matter, Parts per million (ppm), 325 Pasteur, Louis, 703, 833 Pathway intermediates, 953 Pauli exclusion principle, 199 Pauling, Linus, 228, 804 Pectinase, 838, 839, 840 Pellagra, 898 Pentane, 176, 477 Pentosans, 739 Pentoses, 728, 739–740 Pepsin, 909 Pepsinogen, 909 Peptide bonds, 800 Peptide linkage, 800 Percent composition of compounds, 129–132 from experimental data, 132 from formula, 130–131 Percent yield, 182 Percocet, 912 Periodic table, 48–50 actinide series and, 206 alkali metals and, 48 alkaline earth metals and, 48 electron structures and, 203–208 element arrangement and sublevels, 206 groups or families and, 48, 204 halogens and, 48 inner transition elements, 206 lanthanide series and, 206 metalloids, 50 metals and, 49 noble gases and, 48 nonmetals, 49–50 outermost electron configurations, 208 periods and, 204 representative elements and, 48, 204, 206 transition elements and, 48, 204, 206 valence electron configurations, 204–205 Periodic trends in atomic properties, 214–217 atomic radius, 214–215 ionization energy, 216–217 metals and nonmetals, 214 Periods of elements, 204 Peripheral membrane protein, 781 Pernicious anemia, 898 Petroleum, 72 cracking of, 518–519 hydrocarbons and, 473 uses of, 491–494 pH changes caused by HCl and NaOH, 403 common applications of, 365–366 of common solutions, 364 control of, 401–403 enzyme catalysis and, 843–844 importance of, 365 scale of acidity and basicity, 363–364 test paper, 365 using logarithms and, 364 Phases, matter and, Phenol-formaldehyde polymers, 621–622 Phenolics, 621–622 Phenolphthalein, 365, 585 Phenols common phenols, 584–585 naming of, 584 polyphenols, 586 production of, 587 properties of, 586–587 spacefilling model of, 584 Phenyl group, 531 Phenylacetic acid, 965–966 Phenylalanine, 746, 976 Phenylketonuria (PKU), 746, 976 Phosphate anhydride bond, 927 Phosphate anhydride bonds, 927, 929 Phosphate bonds, high-energy, 926–928 Phosphate esters, 661, 855–856 Phosphate system, as buffer in red blood cells, 403 Phosphatidic acids, 771 Phosphatidylcholines, 772 Phosphatidylethanolamines, 772–773 Phospholipids, 771–773 classification of, 765 phosphatidic acids, 771 phosphatidylcholines, 772 phosphatidylethanolamines, 772–773 shape of, 777 Phosphoric acid, esters and anhydrides of, 660–661 Phosphorous, 202 Phosphorus pentachloride, 109 Phosphorylated substrates, 929–930 Phosphorylation, 928–933 Photochemical process, 282 Photochromic glass, 421 Photons, 196 Photosynthesis, 921, 922–923, 934–935, 940 Photosynthetic electron-transport pathway, 935 Physical changes, 64 Physical properties, 62 Physical states of matter, 6–7 Physiological saline solution, 338 Pi bonds, 506–507 Pi electron clouds, 529 Planck, Max, 197 Plane-polarized light, 701–702 Plant cell bioenergetics, 919–920 Plant pigments, 511 Plant sterols, 778 Plaque formation in atherosclerosis, 777 Plasminogen activators, 840 Plastic recycling, 553–554 Plasticizers, 552 Plastics, 549–550 Plexiglas, 615 Plutonium-239, 455 Poison ivy, 585 Polar covalent bonds, 227 Polarimeter, 702 Polarizers, 701 Polaroid filters, 701 Polyamides, 675–676 Polyatomic compounds, 113 Polyatomic ions compounds containing, 111–112, 236–237 oxidation numbers in, 414 Polyatomic molecules, 100 Polycyclic aromatic compounds, 535–536 Polydeoxyribonucleotide, 858 Polyesters, 651–653 Polyethylene, 548–550 Polyethylene recycling, 555 Polyhydroxy alcohols, 568 Polymerization, 548 Polymers addition polymer, 549 addition polymer recycling, 553–554 addition polymerization, 550–553 butadiene polymers, 554–556 condensation polymers, 549, 621–622 copolymers, 556 geometric isomerism in, 557–558 macromolecules, 548 from modified ethylene monomers, 551 phenol-formaldehyde polymers, 621–622 synthetic polymers, 548–549 thermoplastic polymers, 550 thermosetting polymers, 550 types of, 549–550 hein_index_I1-I18hr1.qxd 11/15/10 1:28 PM Page I-15 INDEX Polynucleotides, 857–859 Polypeptides configurations, 804 Edman degradation and, 823–824 formation of, 800–803 primary structure determination and, 822–824 primary structures and functions of, 802 Sanger’s reagent and, 822–823 Polyphenols, 586 Polyribonucleotide, 857 Polysaccharide complex, 755–756 Polysaccharides, 726, 895 Polysaccharides derived from glucose, 750–754 cellulose, 752–754 glycogen, 751 starch, 751 Polysubstituted benzenes, 533–535 Polyunsaturated fats, 896 Polyunsaturated fatty acids, 766 Polyvinyl chloride, 489, 526, 552 Popcorn popping, 70 Positive nitrogen balance, 976 Positron emission tomography (PET), 459 Potassium dichromate, 575 Potassium in diet, 900 Potassium permanganate, 111–112, 318, 575 Potassium reactions with water, 306 Potassium sulfide, 103 Potato tuber cells, 751 Potential energy, 67 Pressure effect on solubility, 321 of gases, 254–255 inverse PV relationship and, 257 molecules and temperature and, 255–256 volume of gas and, 258 Primary alcohol, 566–567 Primary structures of protein, 804 Principle energy levels, 198–199 Problem solving, 4, 67 Procaryotes, 921 Procaryotic cell, 920 Product inhibition, 846 Productive binding hypothesis, 843 Products, 66, 144 Progesterone, 955 Programmed cell death, 873 Prolactin, 955 Propanal, 604 Propane, 475–477 Propane chlorination, 487, 490 Propanetriol, 583 Propanol, 572, 582 Propene, 521–522 Propionic acid, 637 Prostaglandins, 767 Proteases, 838–840 Proteins See also Globular proteins amino acid units and, 804 amino acids in, 794–795 biosynthesis of, 874–876 catalytic proteins, 808 common amino acids derived from, 796–797 complete and incomplete, 797 conjugated proteins, 794 defensive proteins, 808 deficiency and, 897 denaturation and, 817–818 in diet, 897 electrophoresis and, 820–821 engineering of, 878 environmental changes and, 817–818 fibrous proteins, 808–809 functions of, 807–808 globular proteins, 809–817 membrane transport and, 781 motion/movement and, 808 primary structure of, 804 protein domains, 814 quaternary structure of, 807 regulatory proteins, 808 ribbon structures for, 814 secondary structure of, 805–806 simple proteins, 794 storage proteins, 807 structural support and, 807 structure-function connection, 794–795 structure loss and, 817–819 structure of, 804–807 tertiary structure of, 806–807 tests for, 819–822 transport proteins, 808 Proteolytic enzymes, 819 Protons, 86–87 Proximity catalysis, 843 Prozac, 846 Pure Food and Drug Act (1906), 903 Pure substances, distinguishing mixtures from, Purines, 852–853, 859 Pyranose sugars, 734 Pyridoxine, 898–899 Pyrimidine, 852–853 Pyrimidines, 859 Pyrolysis, 518–519 Pyroxylin, 753 Pyruvate, 946, 950 Q Quadratic equation, 397 Quanta, 197 Quantitative composition of compounds calculating empirical formulas, 134–136 I-15 calculating molecular formula from empirical formula, 137–138 empirical formula vs molecular formula, 132–133 molar mass of compounds, 126–129 the mole and, 122–124 percent composition of compounds, 129–132 Quantum mechanics, 198 Quaternary ammonium salts, 681–682 Quaternary structure of proteins, 807 R Racemic mixtures, 711–713 Rad (radiation absorbed dose), 451 Radiation acute damage from, 458–460 biological effects of, 458–460 genetic effects of, 460 long-term damage from, 460 Radiation units, 451 Radioactivity discovery of, 442–443 measurement of, 450–451 radioactive decay, 443 radioactive disintegration series, 448–449 radioactive iodine, 459 Radium isotopes, 443 Rates of reaction, 382–383 Reactants, 66, 144 Reaction-energy profile, 834 Reaction mechanisms, 521 Reaction rates, 382–383 Reactive oxygen species, 925 Real gases, 279–282 Rebaudioside A, 745–746 Rebiana, 745–746 Recombinant DNA, 878 Recommended Dietary Allowance (RDA), 892 Red blood cells, 338 Red dye No 2, 903 Redox coenzymes, 923–925 Redox reactions of monosaccharides, 746–750 Reduction aldehydes and ketones and, 612–613 amides and nitriles and, 682 aromatic nitro compounds and, 682 monosaccharides and, 747–748 reducing sugars, 748–749 Reformulated gasoline, 493–494 Regulatory proteins, 808, 814 Rem (roentgen equivalent to man), 451 Remineralizing therapies, 385 Renal threshold, 956 Replication, 864–865 Representative elements, periodic table and, 48, 204, 206 hein_index_I1-I18hr1.qxd 11/15/10 1:28 PM Page I-16 I-16 INDEX Resin drugs, 778 Resonance structures, 235 Resorcinol, 584 Restricted calorie diets, 894 Restriction endonucleases, 877 Reverse osmosis, 338 Reversible chemical reactions, 382 Rhizobium bacteria, 974 Riboflavin, citric acid cycle and, 950 Ribofuranose, 739 Ribonucleic acid (RNA) differences from DNA, 867–868 functions of, 858 genetic code and, 871–872 genetic control and, 870–871 genetic transcription and, 867–871 health and, 870 messenger RNA, 868–869 micro RNA, 871 protein biosynthesis and, 874–876 small interfering RNA, 870, 871 small nuclear RNA, 871 small nucleolar RNA, 871 transcription and, 869 transfer RNA, 868–869 Ribonucleosides, 854 Rickets, 898 Roentgen (R), 451 Roentgen, Wilhelm, 101 Roentgen, William Conrad, 442 Roentgenium, 450 Rounding off, 18 Rubber, 555–558 Rubberlike synthetic polymers, 556 Rubidium, 92 Rutherford, Ernest, 88, 101, 442, 449 S Saccharin, 745–746 Salicylic acid, 642 Saline water, 303 Saliva, 908–909 Salivary amylase (ptyalin), 908 Salivary digestion, 908–909 Salt water, 84, 103 Salts, 356 acid-base properties of, 401 concentration of, 900 dissociation and, 358–359 formation of, 683–684 Sand filtration, water, 307 Sanger, Frederick, 804, 822 Sanger’s reagent, 822–823 Saponification, 653–654, 657 Saturated acids, 764 Saturated compounds, 468 Saturated hydrocarbons See Alkanes Saturated monocarboxylic acids, 638 Saturated solutions, 321–322 Savinase, 844 Saytzeff’s rule, 577 Scientific approach to problem solving, Scientific laws, Scientific method, 4–5 hypothesis and, scientific laws and, theory and, 4–5 Scientific notation, 14–15 Scintillation camera, 459 Scintillation counter, 450 Screening, water, 307 Scurvy, 898 SDS (sodium dodecyl sulfate) electrophoresis, 821 Seaborg, Glenn, 101 Seawater, mass of, 44–45 Secondary alcohol, 566–567 Secondary structure of proteins, 805–806 Secretin, 955 Sedimentation, water, 307 Selenium, 900 Semipermeable membranes, 338 Serine, 711 Serotonin reuptake, 846 Sevoflurane, 488 Shrödinger, Erwin, 197 Sickle-cell anemia, 811–812 Side-chain oxidation, 539 Side chains, amino acids and, 795 Sigma bonds, 475, 507 Significant figures addition or subtraction and, 19–20 in calculations, 18–21 defined, 16 multiplication or division and, 18–19 rounding off and, 18 rules for counting, 17 Silicon, 202, 900 Silicon wafers, 318 Silver nitrate and copper reaction, 157 Simple lipids, 765–770 eicosanoids, 767–768 fats and oils, 768–769 fatty acids, 765–767 waxes, 769–770 Simple proteins, 794 Simple sugars, 726 Single-displacement reactions, 153–154 Sitostanol ester, 778 Sitosterol, 778 Skeletal muscle composition, 931 Skeletal muscle work, organ cooperation and, 943 Skin cleaners, 840 moisturizers, 583 transdermal patches and, 782 Sleeping, metabolic energy and, 942 Sliding lament model, 932 Small interfering RNA (siRNA), 870–871 Small intestine, 911 Small nuclear RNA (snRNA), 871 Small nucleolar RNA (smoRNA), 871 Smog, 281 Soaps, 657–660 cleansing action of, 658 fighting infection and, 660 Sodium atomic structure and, 202 chlorine atoms reacting with, 219 in diet, 900 electron arrangements and, 219 reactions with water, 305 relative radii of, 220 Sodium atom, 201 Sodium benzoate, 645, 903 Sodium borohydride, 612 Sodium bromide, 103 Sodium chloride, 335 as compound, 53 crystal, 220 dissolution of, 320 formation, 219–220 Sodium fluoride formation, 222 Sodium hydrogen carbonate, 647 Solar flares, 456 Solar radiation, 162 Solids common materials in, definition of, densities of, 35 dissolving rate of, 323–324 physical properties of, Solubility, 318–319 of alkali metal halides in water, 320 of common ions, 319 nature of, 319–320 pressure effect on, 321 temperature effect on, 320–321 of various compounds in water, 321 Solubility product constant, 398–400 Soluble fiber, 778, 895 Solutes, 317, 319–320 Solutions colligative properties of, 333–335 common types of, 317 concentration of, 319, 325–333, 331 dilute solutions, 325 dilution problems and, 332 dissolving solid rates, 323–324 factors related to solubility, 319–323 general properties of, 317–318 mass percent solution, 325–327 mass/volume percent, 327 molarity and, 327–329 osmosis and osmotic pressure, 338–339 permanency and, 318 hein_index_I1-I18hr1.qxd 11/15/10 1:28 PM Page I-17 INDEX as reaction medium, 324–325 saturated solutions, 321–322 solid dissolving rate and, 324 solubility and, 318–319 solution maps, 24 supersaturated solutions, 322 unsaturated solutions, 322 volume percent, 327 Solvents, 317, 319–320 Sorbitol, 748 Soybeans, 878 Space shuttle, 71 Specific gravity, 36 Specific heat, 68 Specific rotation, 702 Spectator ions, 366 Speed, waves and, 195 Spherical molecules, 231 Sphingolipids, 765, 773–774, 777 Spin, 198–199 Stable nuclides, 445 Standard conditions, gas volumes and, 264–265 Standard temperature and pressure (STP), 264–265 Stanford Linear Accelerator Center, 449 Starch, 751 Starvation and ketosis, 973 Statin drugs, 846 Stealth drug delivery, 778 Steam locomotive, 928 Stearic acid, 637, 764, 967 Stereoisomers, 701 Steroids, 765, 775–776 Sticky ends, 878 Stirring, solid dissolving rate and, 324 Stock System, 106 Stoichiometry, 169–171 Stomach acid, 819 Stoney, G J., 85 Storage proteins, 807, 810, 813 Strain hypothesis, 843 Strassmann, Fritz, 451 Streptomyces, 618 Striated muscles, 931 Stroke, 840, 845, 952 Strong electrolytes, 360–361 Strontium-90 isotopes, 460 Structural support, proteins and, 807 Structure-function connection, 794–795 Subatomic parts of atom, 85–87 electrons, 86 general arrangement of, 88–89 neutrons, 88 protons, 86 subatomic particles, 87–88 Subcutaneous fat, 968 Sublevels of energy, 198–200 Sublimation, 292 Subscripts, chemical formulas and, 54 Substance P, 802 Substance properties, 62–63 Substances, Substitution reactions, 484, 537–538 Substrate-level phosphorylation, 929–931, 948 Substrates, 834 Subtraction, significant figures in, 19–20 Succinic acid, 641–642 Sucralose, 745 Sucrose, 741, 743, 834, 895–896 Sudden infant death syndrome (SIDS), 579 Sugar, 63 Sugar alcohols, 748 Sugar cane, 727 Sugar high, 730 Sugar substitutes, 745 Sugar sweetness, 745 Sugars, health problems and, 745 Sulfates, 225 Sulfur atomic structure and, 202 mixture with iron, number of neutrons in, 93 Sunflower, 491 Sunglasses, 421 Sunscreens, 532 Super-ion battery, 430 Superabsorbants, 527 Superimposable molecules, 703 Superoxide, 926 Supersaturated solutions, 322 Supersolvents, 684 Surface tension, liquids and, 293–294 Sweeteners, 744–746 Switchgrass, 651 Symbols of common elements, 46–47 Symbols of elements derived from early names, 47 Synthetic detergents, 657–660 Synthetic polymers, 548–549 Synthetic rubbers, 517, 556, 558 Systems, matter and, T Table salt, 127 Table sugar, 741 Tartaric acid, 714–715 Teflon, 489 Temperature dependence of pressure on, 255–256 effects on equilibrium, 390 effects on solubility, 320–321 enzyme catalysis and, 843–844 gas volume and, 261 measurement of, 16, 30–34 solid dissolving rate and, 323 Termination codons, 871 Termination of polypeptide chain, 875–876 I-17 Tertiary alcohols, 566–567, 574 Tertiary amines, 681 Tertiary structure of proteins, 806–807 Terylene synthetic textiles, 652 Testosterone, 955 Tetrahedral structure, 239–240, 468 Tetrahydrocannabinol, 585 Tetrose, 728 Thalidomide, 712 Theoretical yield, 182 Theory, scientific method and, 4–5 Thermal energy, 30 Thermoplastic polymers, 550 Thermosetting polymers, 550 Thiamin, 898 Thiamine, citric acid cycle and, 950 Thiamine hydrochloride, 682 Thin-layer chromatography (TLC), 820 Thioester, 967 Thiols, 592 Thionyl chloride, 647 Thompson, Benjamin, Thomson, J J., 85 Thomson model of the atom, 86 Three Mile Island accident, 454 Thymidine, 854 Thymine, 853 Thymol, 585 Thyrotropin-releasing hormone, 802 Thyroxine, 797, 955 Thyroxine crystal, 953 Titration, 366–367 TNT, 534 Tollens test, 611 Tolualdehyde, 605 Toluic acid, 640 Toluidines, 679 Torricelli, E., 254 Total ionic equation, 368 Trace elements, 900–901 Trans fats, 230, 517 Transamination, 977 Transcription, 869 Transdermal patches, 782 Transfer RNA (tRNA), 868–869, 874–876 Transferases, 834 Transition elements, 48, 204, 206 Transition states, 835 Translation, 874 Transmutation of elements, 449–450 Transport proteins, 808, 810–812, 813 Transuranium elements, 458 Triacylglycerols, 654–657, 769, 964, 969 Trienes, 517 Triglycerides, 654–655 Trigonal planar molecular shape, 237 Trigonal planar structure, 239 Trimethylamine, 681 hein_index_I1-I18hr1.qxd 11/15/10 1:28 PM Page I-18 I-18 INDEX Triose, 727–728 Trypsin, 910 Tryptophan, 797 Tumor-suppressor genes, 872–873 Turnover number, 837–838 Two-carbon chop, 966 Two-dimensional electrophoresis, 821–822 Tylenol, 912 Tyndall effect, 374 Type I diabetes mellitus, 957 Tyrosine, 797 U Ultraviolet light, 532 Ultraviolet radiation, 280 Uncertainty, measurement and, 15–17 Unsaturated acids, 764 Unsaturated carboxylic acids, 640 Unsaturated compounds, 468 Unsaturated fats, 521, 525 Unsaturated fatty acids, 766, 896 Unsaturated hydrocarbons alkene chemical properties, 520–525 alkene nomenclature, 509–511 alkene preparation and physical properties, 518–520 alkyne nomenclature and preparation, 525–526 alkyne physical and chemical properties, 526–527 aromatic hydrocarbon chemical properties, 537–539 aromatic hydrocarbon sources and physical properties, 536–537 aromatic hydrocarbon structure, 528–530 bonding in, 506–508 cycloalkenes, 517–518 geometric isomerism in alkenes, 511–517 polycyclic aromatic compounds, 535–536 Unsaturated solutions, 322 Unstable nuclides, 445 Uracil, 853 Uranium disintegration series, 449 enriched, 455 isotopes, 443 oxide, 455 uranium-235, 455 uranium-238, 455 Urea, 676–677 Urea cycle, 979–981 Urea synthesis, 979 Uridine, 854 V Valence electrons, 202, 204–205 Valence shell electron pair repulsion (VSEPR) model, 238–239 Valence shell electron pair repulsion theory, 468 Valeric acid, 637 Van de Graaf electrostatic generator, 449 Vanadium, 900 Vanilla bean, 614 Vanillin, 585 Van’t Hoff, J H., 703 Vapor pressure, 292–293 Vapor pressure curves, 295, 334 Vaporization, 291–292 Vascular endothelial growth factor, 801 Vasopressin, 802–803, 955 Vegetable protein, 839 Vegetarian diet, 897 Very-low-density lipoproteins (VLDL), 777 Vicodin, 912 Villard, Paul, 442 Vinegars, 637 Vinyl polymerization, 550 Vital-force theory, 467 Vitamin A, 899 Vitamin C, 899 Vitamin D, 899 Vitamin E, 899 Vitamin K, 899 Vitamins, 897–899 Volatile substances, 293 Voltaic cells, 425–430 Volume common volume relationships, 29 effect on equilibrium, 388–389 of equal masses, 35 inverse PV relationship and, 257 measurements, 29–30 volume percent, 327 volume-volume calculations, 277–278 Volumetric flasks, 329 Von Gierke disease, 945 Vulcanization, 556 W Warfarin, 712 Water, 303–307 arsenic contamination, 309 atomic composition of, 83 balance, 901 as compound, 53 crystallization and, 299 electrolysis of, 65, 71 formation of, 305 gas solubility in, 321 geometric shape of, 237 Hϩ and OHϪ concentration relationship in, 394 hydration and, 301 hydrogen bonding and, 299 ice and water in equilibrium, 303–304 ion product constant for, 393–395 ionization of, 362–363 meniscus of, 294 mole of, 127 molecular structure of, 304–305 physical properties of, 63, 295, 299, 303–304 purification of, 307–310 reactions with metal and nonmetal oxides, 306–307 reactions with metals and nonmetals, 305–306 specific heat of, 68 vapor pressure curves for, 334 vapor pressure-temperature curves for, 295 Water soluble vitamins, 898 Watson, James, 859–860, 863 Watson-Crick model of DNA, 861 Wave mechanics, 197–198 Wavelengths, 195 Waxes, 765, 769–770 Weak electrolytes, 360–361 Weight, determination of, 27 Wetland blanket for global warming, 281 Wetphal, James A., 33 Wilkins, Maurice, 860 Wöhler, Friedrich, 467 Woody plants, energy and, 72 X X-ray diffraction, 529 X-ray technology, 442, 460 Xanthoproteic test, 819 Xylene, 533 Xylose, 739 Y Yellow dye No 5, 903 Yield calculations, 182–184 Yogurt, 642 Z Zero-fat diets, 969 Ziegler, Karl, 557 Ziegler-Natta catylysts, 557 Zinc, 900 Zinc-copper voltaic cell, 427–430 Zinc-mercury cells, 428 Zinc metal in hydrochloric acid, 153 Zinc sulfate, 103 Zwitterions, 798–799 – Current ACS and IUPAC Preferred U.S Hydrogen Period Na Atomic masses are based on carbon-12 Elements marked with † have no stable isotopes The atomic mass given is that of the isotope with the longest known half-life He Helium 1.008 2A Li Be Lithium Beryllium Boron Carbon Nitrogen Oxygen Fluorine Neon 6.941 9.012 10.81 12.01 14.01 16.00 19.00 20.18 13 14 15 16 17 18 Al Si P S Cl Ar Aluminum Silicon Phosphorus Sulfur Chlorine Argon 26.98 28.09 30.97 32.07 35.45 39.95 Sodium 22.99 13 3A Transition Elements 11 12 Na Mg Sodium Magnesium 22.99 24.31 3B 4B 5B 6B 7B 8B 10 11 1B 12 2B 14 4A 15 5A 16 6A 17 7A 4.003 10 B C N O F Ne 19 20 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36 K Ca Sc Ti V Cr Mn Fe Co Ni Cu Zn Ga Ge As Se Br Kr Potassium Calcium Scandium Titanium Vanadium Chromium Manganese Iron Cobalt Nickel Copper Zinc Gallium Germanium Arsenic Selenium Bromine Krypton 39.10 40.08 44.96 47.87 50.94 52.00 54.94 55.85 58.93 58.69 63.55 65.39 69.72 72.61 74.92 78.96 79.90 83.80 37 38 39 40 41 42 43 44 45 46 47 48 49 50 51 52 53 54 Rb Sr Y Zr Nb Mo Tc Ru Rh Pd Ag Cd In Sn Sb Te I Xe Rubidium Strontium Yttrium Zirconium Niobium Ruthenium Rhodium Palladium Silver Cadmium Indium Tin Antimony Tellurium Iodine Xenon 85.47 87.62 88.91 91.22 92.91 101.1 102.9 106.4 107.9 112.4 114.8 118.7 121.8 127.6 126.9 131.3 85 86 Rn Molybdenum Technetium 95.94 98.00† 55 56 57 Cs Ba La Cesium Barium Lanthanum Hafnium Tantalum Tungsten Rhenium Osmium Iridium Platinum Gold Mercury Thallium Lead Bismuth 132.9 137.3 138.9 178.5 180.9 183.8 186.2 190.2 192.2 195.1 197.0 200.6 204.4 207.2 209.0 104 105 106 107 108 109 110 111 Rf Db Sg Bh Hs Mt Ds Rg Seaborgium 266† Bohrium 264† Hassium 277† 87 88 89 Fr Ra Ac Francium 223 † Radium 226 † Actinium 227 † * * * 72 73 74 75 76 77 78 79 80 81 82 83 Hf Ta W Re Os Ir Pt Au Hg Tl Pb Bi Rutherfordium Dubnium 261† 262† 84 Po Polonium 209† At Astatine 210† Radon 222† colors indicate placement of the outermost electrons Meitnerium Darmstadtium Roentgenium 268† 271† 272† s orbitals d orbitals p orbitals f orbitals Inner Transition Elements * Lanthanide Series * * Actinide Series 58 59 60 61 62 63 64 65 66 67 68 69 70 71 Ce Pr Nd Pm Sm Eu Gd Tb Dy Ho Er Tm Yb Lu Samarium Europium Gadolinium Terbium Dysprosium Holmium Erbium Thulium Ytterbium Lutetium 150.4 152.0 157.3 158.9 162.5 164.9 167.3 168.9 173.0 175.0 103 Cerium 140.1 Praseodymium Neodymium Promethium † 140.9 144.2 145 90 91 92 93 94 95 96 97 98 99 100 101 102 Th Pa U Np Pu Am Cm Bk Cf Es Fm Md No Thorium Protactinium Uranium Neptunium 232.0 231.0 238.0 237 Plutonium † Americium † Curium † Berkelium † 244 243 247 247 Californium Einsteinium † † 251 252 Fermium † 257 Mendelevium Nobelium † † 258 259 Lr Lawrencium † 262 Page ii 11 2:28 PM Atomic number Symbol Name Atomic mass H 8/2/10 18 8A hein_front_hr.qxd 1A Noble Gases Periodic Table of the Elements Group hein_front_hr.qxd 8/2/10 2:28 PM Page iii Atomic Masses of the Elements Based on the 2005 IUPAC Table of Atomic Masses Name Actinium* Aluminum Americium* Antimony Argon Arsenic Astatine* Barium Berkelium* Beryllium Bismuth Bohrium* Boron Bromine Cadmium Calcium Californium* Carbon Cerium Cesium Chlorine Chromium Cobalt Copper Curium* Darmstadtium* Dubnium* Dysprosium Einsteinium* Erbium Europium Fermium* Fluorine Francium* Gadolinium Gallium Germanium Gold Hafnium Hassium* Helium Holmium Hydrogen Indium Iodine Iridium Iron Krypton Lanthanum Lawrencium* Lead Lithium Lutetium Magnesium Manganese Symbol Ac Al Am Sb Ar As At Ba Bk Be Bi Bh B Br Cd Ca Cf C Ce Cs Cl Cr Co Cu Cm Ds Db Dy Es Er Eu Fm F Fr Gd Ga Ge Au Hf Hs He Ho H In I Ir Fe Kr La Lr Pb Li Lu Mg Mn Atomic Number 89 13 95 51 18 33 85 56 97 83 107 35 48 20 98 58 55 17 24 27 29 96 110 105 66 99 68 63 100 87 64 31 32 79 72 108 67 49 53 77 26 36 57 103 82 71 12 25 Atomic Mass 227 26.981538 243 121.760 39.948 74.92160 210 137.327 247 9.012182 208.98038 264 10.811 79.904 112.411 40.078 251 12.0107 140.116 132.90545 35.4527 51.9961 58.933200 63.546 247 271 262 162.500 252 167.26 151.964 257 18.9984032 233 157.25 69.723 72.61 196.96655 178.49 277 4.002602 164.93032 1.00794 114.818 126.90447 192.217 55.845 83.80 138.9055 262 207.2 6.941 174.967 24.3050 54.938049 Name Meitnerium* Mendelevium* Mercury Molybdenum Neodymium Neon Neptunium* Nickel Niobium Nitrogen Nobelium* Osmium Oxygen Palladium Phosphorus Platinum Plutonium* Polonium* Potassium Praseodymium Promethium* Protactinium Radium* Radon* Rhenium Rhodium Roentgenium* Rubidium Ruthenium Rutherfordium* Samarium Scandium Seaborgium* Selenium Silicon Silver Sodium Strontium Sulfur Tantalum Technetium* Tellurium Terbium Thallium Thorium Thulium Tin Titanium Tungsten Uranium Vanadium Xenon Ytterbium Yttrium Zinc Zirconium Symbol Mt Md Hg Mo Nd Ne Np Ni Nb N No Os O Pd P Pt Pu Po K Pr Pm Pa Ra Rn Re Rh Rg Rb Ru Rf Sm Sc Sg Se Si Ag Na Sr S Ta Tc Te Tb Tl Th Tm Sn Ti W U V Xe Yb Y Zn Zr Atomic Number 109 101 80 42 60 10 93 28 41 102 76 46 15 78 94 84 19 59 61 91 88 86 75 45 111 37 44 104 62 21 106 34 14 47 11 38 16 73 43 52 65 81 90 69 50 22 74 92 23 54 70 39 30 40 * This element has no stable isotopes The atomic mass given is that of the isotope with the longest known half-life Atomic Mass 268 258 200.59 95.94 144.24 20.1797 237 58.6934 92.90638 14.00674 259 190.23 15.9994 106.42 30.973762 195.078 244 209 39.0983 140.90765 145 231.03588 226 222 186.207 102.90550 272 85.4678 101.07 261 150.36 44.955910 266 78.96 28.0855 107.8682 22.989770 87.62 32.066 180.9479 98 127.60 158.92534 204.3833 232.0381 168.93421 118.710 47.867 183.94 238.0289 50.9415 131.29 173.04 88.90585 65.39 91.224 hein_end_hr.qxd 8/2/10 2:29 PM Page iv Names, Formulas, and Charges of Common Ions Positive Ions (Cations) 1± 2± 3± 4± 5± Ammonium Copper(I) (Cuprous) Hydrogen Potassium Silver Sodium Barium Cadmium Calcium Cobalt(II) Copper(II) (Cupric) Iron(II) (Ferrous) Lead(II) Magnesium Manganese(II) Mercury(II) (Mercuric) Nickel(II) Tin(II) (Stannous) Zinc Aluminum Antimony(III) Arsenic(III) Bismuth(III) Chromium(III) Iron(III) (Ferric) Titanium(III) (Titanous) Manganese(IV) Tin(IV) (Stannic) Titanium(IV) (Titanic) Antimony(V) Arsenic(V) Negative Ions (Anions) NH 4+ Cu + H+ K+ Ag + Na + Ba2+ Cd2+ Ca2+ Co 2+ Cu2+ 1– Fe 2+ Pb 2+ Mg 2+ Mn2+ Hg 2+ 2+ Ni Sn2+ Zn2+ Al3+ Sb 3+ As3+ Bi3+ Cr 3+ Fe 3+ 2– Ti3+ Mn4+ Sn4+ Ti4+ 3– Sb 5+ As5+ Acetate Bromate Bromide Chlorate Chloride Chlorite Cyanide Fluoride Hydride Hydrogen carbonate (Bicarbonate) Hydrogen sulfate (Bisulfate) Hydrogen sulfite (Bisulfite) Hydroxide Hypochlorite Iodate Iodide Nitrate Nitrite Perchlorate Permanganate Thiocyanate Carbonate Chromate Dichromate Oxalate Oxide Peroxide Silicate Sulfate Sulfide Sulfite Arsenate Borate Phosphate Phosphide Phosphite C2H 3O 2BrO 3Br ClO 3ClClO 2CN FHHCO 3HSO 4HSO 3OH ClO IO 3INO 3NO 2ClO 4MnO 4SCN CO 23 CrO 24 Cr2O 27 C2O 24 O 2O 22 SiO 23 SO 24 S2SO 23 AsO 34 BO 33 PO 34 P 3PO 33 hein_end_hr.qxd 8/2/10 2:29 PM Page v Prefixes and Numerical Values for SI Units Prefix Symbol Numerical value Power of 10 equivalent exa peta tera giga mega kilo hecto deka — deci centi milli micro nano pico femto atto E P T G M k h da — d c m n p f a 1,000,000,000,000,000,000 1,000,000,000,000,000 1,000,000,000,000 1,000,000,000 1,000,000 1,000 100 10 0.1 0.01 0.001 0.000001 0.000000001 0.000000000001 0.000000000000001 0.000000000000000001 1018 1015 1012 109 106 103 102 101 100 10-1 10-2 10-3 10-6 10-9 10-12 10-15 10-18 SI Units and Conversion Factors Length Mass SI unit: meter (m) = = centimeter = inch = meter kilometer mile angstrom = = = = 1000 millimeters 1.0936 yards 0.3937 inch 2.54 centimeters (exactly) 0.62137 mile 5280 feet 1.609 kilometers 10-10 meter SI unit: kelvin (K) K °C °C °F = -273.15°C = - 459.67°F = °C + 273.15 (°F - 32) = 1.8 = (°F - 32) = 1.8(°C) + 32 SI unit: cubic meter (m3) SI unit: kilogram (kg) kilogram gram pound ton = = = = = = = = = 1000 grams 2.20 pounds 1000 milligrams 453.59 grams 0.45359 kilogram 16 ounces 2000 pounds 907.185 kilograms 28.3 grams liter gallon quart ounce atomic mass unit = 1.6606 * 10-27 kilograms Temperature 0K Volume SI unit: joule (J) calorie = kg m2>s2 = 0.23901 calorie = 4.184 joules 1000 milliliters 10-3 m3 dm3 1.0567 quarts quarts pints 3.785 liters 32 fluid ounces 0.946 liter cups fluid ounce = 29.6 mL Energy joule = = = = = = = = = = Pressure SI unit: pascal (Pa) pascal atmosphere = = = = = kg>(ms2) 101.325 kilopascals 760 torr 760 mm Hg 14.70 pounds per square inch (psi) ... INTRODUCTION TO GENERAL, ORGANIC, AND BIOCHEMISTRY Tenth Edition This page intentionally left blank hein_ FM_i-xxvi_hr1.qxd 11/16/10 3:43 PM Page iii INTRODUCTION TO GENERAL, ORGANIC, AND BIOCHEMISTRY. .. Editor Editorial Project Coordinator Associate Editor Marketing Manager Production Manager Production Editor Cover Designer Executive Media Editor Media Editor Photo Department Manager Photo... tenth edition of Introduction to General, Organic, and Biochemistry is to present chemistry in a clear, engaging manner to stimulate students to see the relationship of chemistry to their chosen