Front Cover: Cholesterol (C27H46O) is a well-known molecule synthesized in the liver and found in almost all body tissues While cholesterol is a necessary component of healthy cell membranes, high blood cholesterol levels are associated with an increased risk of developing coronary artery disease, heart attack, and stroke Since cholesterol is insoluble in the blood, it is transported throughout the body in water-soluble particles called HDLs and LDLs An understanding of the interplay of cholesterol, HDLs, and LDLs in the overall health of an individual begins with a basic knowledge of the structure and properties of these key compounds Student Study Guide/Solutions Manual (ISBN: 0-07-302658-1; ISBN-13: 978-0-07-302658-9) The Student Study Guide/Solutions Manual, prepared by Erin Smith and Janice Gorzynski Smith, begins each chapter with a detailed chapter review organized around the chapter goals and key concepts The Problem Solving section provides a number of examples for solving each type of problem essential to that chapter The Self-Test section of each chapter quizzes chapter highlights, with answers provided Finally, each chapter ends with the solutions to all in-chapter problems, as well as the solutions to all odd-numbered end-of-chapter problems Connect Electronic Homework and Assessment System www.mcgrawhillconnect.com/chemistry MD DALIM #1000127 12/19/08 CYAN MAG YEL BLK SPOTUV McGraw-Hill’s unique homework and assessment system, known as Connect, is an electronic homework and course management system designed for greater flexibility, power, and ease of use than any other system Connect is ideal for preplanned assignments, and is also fully customizable to fit specific course needs Build Assignments Choose from pre-built assignments or create your own using resources within Connect Track Student Progress Assignments are automatically graded An electronic grade book provides reports on progress Share Course Materials Instructors can create and share materials with colleagues Want to learn more? Find your McGraw-Hill representative at www.mhhe.com ISBN 978-0-07-302657-2 MHID 0-07-302657-3 Part of ISBN 978-0-07-727429-0 MHID 0-07-727429-6 www.mhhe.com smi26573_FM.indd i 12/18/08 12:33:29 PM smi26573_FM.indd ii 12/18/08 12:33:32 PM Janice Gorzynski Smith University of Hawai’i at Ma- noa smi26573_FM.indd iii 12/18/08 12:33:36 PM GENERAL, ORGANIC, AND BIOLOGICAL CHEMISTRY Published by McGraw-Hill, a business unit of The McGraw-Hill Companies, Inc., 1221 Avenue of the Americas, New York, NY 10020 Copyright © 2010 by The McGraw-Hill Companies, Inc All rights reserved No part of this publication may be reproduced or distributed in any form or by any means, or stored in a database or retrieval system, without the prior written consent of The McGraw-Hill Companies, Inc., including, but not limited to, in any network or other electronic storage or transmission, or broadcast for distance learning Some ancillaries, including electronic and print components, may not be available to customers outside the United States This book is printed on acid-free paper DOW/DOW ISBN 978–0–07–302657–2 MHID 0–07–302657–3 Publisher: Thomas D Timp Senior Sponsoring Editor: Tamara L Hodge Vice-President New Product Launches: Michael Lange Senior Developmental Editor: Donna Nemmers Marketing Manager: Todd L Turner Senior Project Manager: Jayne L Klein Senior Production Supervisor: Laura Fuller Senior Media Project Manager: Tammy Juran Designer: Laurie B Janssen (USE) Cover Image: Lower right: ©3D4Medical.com/gettyimages, background: ©Andrew Brookes/Corbis Lead Photo Research Coordinator: Carrie K Burger Photo Research: Mary Reeg Supplement Producer: Mary Jane Lampe Compositor: Precision Graphics Typeface: 10/12.5 Times LT Std Printer: R R Donnelley Willard, OH The credits section for this book begins on page C-1 and is considered an extension of the copyright page Library of Congress Cataloging-in-Publication Data Smith, Janice G General, organic, and biological chemistry / Janice Gorzynski Smith — 1st ed p cm Includes index ISBN 978–0–07–302657–2 — ISBN 0–07–302657–3 (hard copy : alk paper) Chemistry—Textbooks I Title QD31.3.S63 2010 540—dc22 2008044484 www.mhhe.com smi26573_FM.indd iv 12/18/08 12:33:38 PM Dedication To my husband Dan, children Erin, Jenna, Matthew, and Zachary, and father Stanley, and in memory of my mother Dorothea and daughter Megan smi26573_FM.indd v 12/18/08 12:33:38 PM About the Author Janice Gorzynski Smith was born in Schenectady, New York, and grew up following the Yankees, listening to the Beatles, and water skiing on Sacandaga Reservoir She became interested in chemistry in high school, and went on to major in chemistry at Cornell University where she received an A.B degree summa cum laude Jan earned a Ph.D in Organic Chemistry from Harvard University under the direction of Nobel Laureate E.J Corey, and she also spent a year as a National Science Foundation National Needs Postdoctoral Fellow at Harvard During her tenure with the Corey group, she completed the total synthesis of the plant growth hormone gibberellic acid Following her postdoctoral work, Jan joined the faculty of Mount Holyoke College where she was employed for 21 years During this time she was active in teaching chemistry lecture and lab courses, conducting a research program in organic synthesis, and serving as department chair Her organic chemistry class was named one of Mount Holyoke’s “Don’t-miss courses” in a survey by Boston magazine After spending two sabbaticals amidst the natural beauty and diversity in Hawai‘i in the 1990s, Jan and her family moved there permanently in 2000 She is currently a faculty member at the University of Hawai‘i at Mānoa, where she teaches a one-semester organic and biological chemistry course for nursing students, as well as the two-semester organic chemistry lecture and lab courses She also serves as the faculty advisor to the student affiliate chapter of the American Chemical Society In 2003, she received the Chancellor’s Citation for Meritorious Teaching Jan resides in Hawai‘i with her husband Dan, an emergency medicine physician She has four children: Matthew and Zachary (scuba photo on page 190); Jenna, a first-year law student at Temple University in Philadelphia; and Erin, a 2006 graduate of Brown University School of Medicine and co-author of the Student Study Guide/Solutions Manual for this text When not teaching, writing, or enjoying her family, Jan bikes, hikes, snorkels, and scuba dives in sunny Hawai‘i, and time permitting, enjoys travel and Hawai‘ian quilting vi smi26573_FM.indd vi 12/23/08 9:33:46 AM Brief Contents 10 Matter and Measurement Atoms and the Periodic Table 32 Ionic Compounds 66 Covalent Compounds 93 Chemical Reactions 121 Energy Changes, Reaction Rates, and Equilibrium 159 Gases, Liquids, and Solids 190 Solutions 228 Acids and Bases 258 Nuclear Chemistry 298 11 Introduction to Organic Molecules and Functional 12 13 14 15 16 17 18 Groups 322 Alkanes 355 Unsaturated Hydrocarbons 379 Organic Compounds That Contain Oxygen, Halogen, or Sulfur 418 The Three-Dimensional Shape of Molecules 449 Aldehydes and Ketones 473 Carboxylic Acids, Esters, and Amides 503 Amines and Neurotransmitters 540 19 20 21 22 23 24 Lipids 569 Carbohydrates 608 Amino Acids, Proteins, and Enzymes 644 Nucleic Acids and Protein Synthesis 682 Digestion and the Conversion of Food into Energy 718 Carbohydrate, Lipid, and Protein Metabolism 744 vii smi26573_FM.indd vii 12/18/08 12:33:46 PM smi26573_FM.indd viii 12/18/08 12:33:55 PM Contents Preface xxii P.A.V.E the Way to Student Learning xxiv Acknowledgments xxvii List of How To’s xxix List of Applications xxx Matter and Measurement 1.1 1.2 1.3 1.4 Chemistry—The Science of Everyday Experience States of Matter Classification of Matter Measurement 1.4A 1.4B 1.4C 1.4D 1.5 The Metric System Measuring Length 10 Measuring Mass 10 Measuring Volume 10 Significant Figures 11 1.5A 1.5B 1.5C 1.6 1.7 Determining the Number of Significant Figures 12 Using Significant Figures in Multiplication and Division 13 Using Significant Figures in Addition and Subtraction 15 Scientific Notation 16 Problem Solving Using the Factor–Label Method 18 1.7A 1.7B 1.7C Conversion Factors 18 Solving a Problem Using One Conversion Factor 19 Solving a Problem Using Two or More Conversion Factors 21 1.8 Focus on Health & Medicine: Problem Solving Using Clinical Conversion Factors 22 1.9 Temperature 24 1.10 Density and Specific Gravity 25 1.10A 1.10B Density 25 Specific Gravity Chapter Highlights 27 27 ix smi26573_FM.indd ix 12/18/08 12:33:55 PM INDEX N-Methylacetamide, 526 Methylamine, 328, 523, 541, 543 3-Methylcyclohexene, 458 Methylcyclopentane, 457 Methylmercury, 59mn Methylpentane, isomers of, 450 Methylpropene, 385 Metric system definition, English equivalents, 12t features of, prefixes, 9, 9t units, 9, 9t, 11t, 12t Mevalonic acid, 571 Micelle, 518, 518f Micro- (prefix), 9t Microliter (µL), 11, 11t Micronutrient, 34, 36f Milli- (prefix), 9, 9t Millicurie (mCi), 310 Milligram (mg), 10, 11t Milliliter (mL), 11, 11t Millimeter (mm), 10, 11t Millimeters of mercury (mm Hg), 193 Mirror image, 451–453, 456 Misoprostol, 599, 600 Mitochondria, 719, 719mn, 720f, 722, 736–738, 736f Mixture definition, 6, 229 examples, 6, 7f heterogeneous, 229 homogeneous, 229 separation into components by physical change, Molar mass calculating, 133–134 definition, 133 relating grams to moles, 134–135 relating grams to number of atoms or molecules, 135–136 using to convert moles to grams, 243–244 Molarity calculating, 241–242 as conversion factor, 242–244 definition, 241 diluting a solution, 244 Mole(s) Avogadro’s law, 202–206 calculations in chemical equations, 136–137 definition, 130 mass–mole conversions, 134–135 moles–molecules conversions, 130–132 Mole ratio, 136–137 Molecular art, 37, 37f Molecular formula, 97 Molecular shape See also specific shapes bent, 109t, 329t alcohols, 421 dimethyl ether, 329 smi26573_EM05_index.indd I-17 I-17 l-dopa, 330 ethers, 432, 433 methanol, 328, 342 thiols, 440 water, 109 Lewis structure, 106–110 linear, 107, 109t, 329t, 342 polarity and, 342 tetrahedral, 107, 108, 109t, 327–328, 329t, 343 three-dimensional, 449–466 trigonal planar, 107, 108, 109t, 329t trigonal pyramidal, 109, 109t, 328, 329t valence shell electron pair repulsion (VSEPR) theory, 107 Molecular solid, 218–219, 218f Molecular weight, 132 Molecule definition, 67, 94 polarity of, 112–114, 113f Molina, Mario, 439mn Molybdenum, as trace element (micronutrient), 36f Mono- (prefix), 106, 107t Monomer, 398–400, 400t Monoprotic acid, 260 Monosaccharide aldoses, 610–612 classification, 610–612 common, 615–616 cyclic forms, 616–621 of fructose, 621 d-glucose, 617–618, 618f Haworth projections, 618–620 d or l forms, 613–615 Fischer projection formulas, 612–613 ketoses, 610–612 multiple chirality centers, 613–615 in nucleosides and nucleotides, 683–687 oxidation, 621, 623–624 properties, 612 reduction, 621, 622 structure, 609, 610 Monosubstituted benzene, 403 Monounsaturated triacylglycerol, 577, 578t Morphine, 550, 550mn, 655 Morton, William, 436 Mountain climber, 209, 209mn Mouthwash, 237, 237mn MRI (magnetic resonance imaging), 317, 317f mRNA See Messenger RNA (mRNA) MTBE (tert-butyl methyl ether), 240, 344 Multiple sclerosis, 587, 588f Multiplication, using significant figures in, 13–15, A-4 Muscone, 486 Mutagen, 703 Mutarotation, 618 Mutation, 703–705 Myelin sheath, 587, 588f Myoglobin, 645f, 665–667, 665mn, 666f Myosin, 645f, 658 Myrcene, 381 Myricyl palmitate, 575 Myristic acid, 573t N N- (prefix), 544 NAD+ and NADH (nicotinamide adenine dinucleotide) ATP yield, 738, 757–758, 758f biological reductions, 486–487 in citric acid cycle, 733–735, 734f as cofactor, 670 description, 728–730, 731t electron transport chain, 736f, 737, 738 fatty acid oxidation, 762, 763f, 764 in glycolysis, 748–749, 748f, 751–752, 752f pyruvate oxidation, 754, 755 structure, 729 Nandrolone, 595 Nano- (prefix), 9t Naphthalene, 404–405 Naproxen, 449, 460, 513 Natural gas, 324, 328mn, 370, 370mn Naturally occurring materials, 2, 2f, 3f Neon electronic configuration, 53 as noble gas in periodic table, 47 Neopentane, 359 Neptunium, 33mn Nerve gas, 673 Net dipole in alkyl halides, 437 in ethers, 433 Net ionic equation, 281 Network solid, 218, 218f Neuron, 556, 557f Neuropeptides, 654–655 Neurotoxin, 433, 433mn Neurotransmitter acetylcholine, 557, 560 description, 556 dopamine, 557, 558, 558f mode of action, 556, 557f norepinephrine, 557, 558f serotonin, 558–559 Neutral solution definition, 275, 275t, 277 salt solution, 283–284, 284t Neutralization reaction, 281 Neutron charge, 37, 38t in isotopes, 40 mass, 37, 38, 38t in mass number, 39 Niacin, 487, 487mn Nickel, as trace element (micronutrient), 36f Nicotine, 133, 540f, 549–550, 549f, 549mn, 560 12/22/08 4:57:18 PM I-18 Night blindness, 597 Nitrate ion as conjugate base, 267t as polyatomic ion, 85t Nitration, 409–410 Nitric acid acid rain, 291, 291f acid strength, 266, 267t as Brønsted–Lowry acid, 260 Nitrite ion, 85t Nitro group, 409 Nitrogen in amides (see Amides) amines, 540–563 atomic composition, 40f bends and, 209 bonding patterns, 96f, 326t as building-block element, 34, 36f, 40f gas in blood, 235 as heteroatom, 325 polyatomic anions containing, 85t Nitrogen heterocycles, 545 Nitrogen monoxide, 136, 136mn, 173, 173f Nitroglycerin, 97, 97f Nitrous oxide, formation of, 180–181 Noble gas notation, of first- and second-row elements, 53–54, 54t Noble gases (Group 8A) definition, 47 electronic configuration, 57t, 67 nonreactivity, 67 in periodic table, 46–47 Nomenclature alcohols, 422–424 aldehydes, 476–477 alkane, 363–367 alkenes and alkynes, 382–384 alkyl halides, 437–438 amide, 508–509 amines, 543–545 anions, 80, 80t benzene derivatives, 403–405 carboxylic acid, 506–507 cations, 79, 79t chirality center, 453mn cis–trans isomers, 385 covalent compounds, 105–106 cycloalkanes, 368–370 definition, 79, 362 ester, 507–508 ethers, 435 ionic compounds, 79–83 with cations from main group metals, 80–81 with metal with variable charge, 80–81 with polyatomic ions, 86–87 IUPAC system, 362, 364–367 ketones, 477–478 new drugs, 362–363 nucleosides, 685, 687t nucleotides, 686, 687t polyatomic ions, 84, 85t polynucleotide, 688–689 smi26573_EM05_index.indd I-18 INDEX prefixes, 107t thiols, 440–441 Nona- (prefix), 107t Nonane, 359t Nonbonded electron pairs, 94 Noncompetitive inhibitor, 672 Nonelectrolyte, 230 Nonmetal(s) anions, 70, 71–72, 77 building-block elements, 34, 36f covalent bonding, 95, 106 definition, 34, 67 ionic bonds, 67 in periodic table, 34, 35f reduction, 149–150 Nonpolar bond, 111, 112t Nonpolar compound London dispersion forces, 210 solubility of, 231, 232–233, 233f Nonpolar molecule, 113–114, 113f, 341–342 Nonrenewable energy, 371 Nonsteroidal anti-inflammatory drug (NSAID), 460, 600 Nonvolatile solute, 246–247 Noradrenaline See Norepinephrine Norepinephrine, 557, 558f, 561 Norethindrone, 391, 391f NSAID (nonsteroidal anti-inflammatory drug), 460, 600 N-Substituted primary amine, 544 Nuclear chemistry, 298–317 detecting and measuring radioactivity, 310–311, 310mn, 310t half-life, 307–309, 308t nuclear reactions, 302–307 alpha emission, 302–303, 302mn balancing equations for, 302–306 beta emission, 303–305, 304f definition, 298 gamma emission, 306–307, 307f nuclear fission, 314–316, 315f nuclear fusion, 314, 316 positron emission, 305–306 radioisotopes, 299–300 half-life, 307–309, 308t medical uses, 304, 304f, 307, 307f, 311–314, 312f–314f types of radiation, 300–301, 301t Nuclear equation balancing, 302–306 description, 302 Nuclear fission, 314–316, 315f Nuclear fusion, 314, 316 Nuclear reactions, 302–307 alpha emission, 302–303, 302mn balancing equations for, 302–306 beta emission, 303–305, 304f definition, 298 gamma emission, 306–307, 307f nuclear fission, 314–316, 315f nuclear fusion, 314, 316 positron emission, 305–306 Nucleic acid, 682–711 See also DNA; RNA components, 686t, 687t nucleosides and nucleotides, 683–688 structure, primary, 389f, 688–690, 689f in viruses, 710–711, 711f Nucleoside, 683–685, 686t Nucleoside analogue, 710, 711 Nucleosome, 692, 692f Nucleotide, 683, 686–688, 686t Nucleus, 38 Numbers estimated digit, 12 exact, 12 inexact, 12 rounding off, 14–15, 14t, A-3 scientific notation, 16–18, 17t, A-1–A-2 significant figures, 11–16, A-2–A-4 Numerator, 21, 23 Nutrition, energy and, 161–162, 161t Nutritional Calorie (Cal), 161–162 Nylon, 121f, 528–529, 528mn O -o (suffix), 403, 437 Octa- (prefix), 107t Octanal, 475 Octane solubility in nonpolar solvent, 232, 233f structure, 359t Octanethiol, 441 Octanoic acid, 516 Octanol, 422 Octet rule, 70, 73, 102 Octylamine, 554, 555 -oic acid (suffix), 506, 508 Oil of wintergreen, 513, 514 Oils See also Triacylglycerols in diet, 579–580 fatty acid composition of common, 578, 578t physical properties, 388, 577, 578 -ol (suffix), 422, 423 Oleic acid, 388, 388t, 389f, 572–573, 573t Olestra, 527–528, 527mn Omega-3 fatty acids, 573, 573mn, 579, 580 Omega-6 fatty acids, 573 -one (suffix), 477 Opium poppy, 550 Oral contraceptives, 390–391, 391f Orbital definition, 49 electron spins, 49mn, 52 energy, 49, 51–52, 52t in principal energy levels, 49–50, 50t shape, 51 Orbital diagram definition, 52 first- and second-row elements, 54t Organelles, 719 Organic chemistry, 323, 323f See also Organic molecules 12/22/08 4:57:18 PM INDEX Organic compounds See also Organic molecules alcohols, 419–432 alkyl halides, 436–440 classifying carbon atoms, 360–361 ethers, 432–436 thiols, 440–442 Organic molecules, 322–347 See also Organic compounds characteristic features, 323–327 drawing, 331–334 condensed structures, 331–332 skeletal structures, 333–334 environmental pollutants, 344–345 functional groups, 334–340, 335t, 337t, 338t, 339f properties, 340–344, 341f, 344t inorganic compounds compared, 340, 341f polarity, 340–343 solubility, 343–344, 344t shapes, 327–331, 329t vitamins, 322, 345–347, 345mn, 346mn, 347f Ortho- (prefix), 403–404 -ose (suffix), 611 -osine (suffix), 685 Osmosis, 246, 249 Osmotic pressure, 249–250, 251f Osteoporosis, 87, 87mn -ous (suffix), 79, 81 Ovalbumin, 669 Oxalic acid, 505 Oxaloacetate, 733–734, 734f Oxalosuccinate, 729 Oxidase, 670 Oxidation of aldehydes, 481, 482–483 blood alcohol screening, 430, 431f coenzymes and, 728–730, 731t definition, 148, 728 examples of, 150f of monosaccharides, 621, 623–624 overview, 428–430, 428f oxidases, 670 results of, 152, 372 β-Oxidation, 761–765, 763f, 765mn Oxidation–reduction (redox) reactions, 148–153 combustion, 372–373 definition, 148 examples, 148–153, 149f, 150f, 151f, 153f half reactions, 149 Oxidative deamination, 768–769 Oxidative phosphorylation, 722, 737–738 Oxide anion, 80t Oxidizing agent, 149, 150, 728–730, 731t, 733, 736, 747, 749 -oxy (suffix), 435 Oxybenzone, 480 Oxygen atomic composition, 40f bonding patterns, 96f, 326t as building-block element, 34, 36f, 40f smi26573_EM05_index.indd I-19 I-19 cardiovascular system and, 97, 97f density, 25t electronic configuration, 53 as heteroatom, 325 polyatomic anions containing, 85t solubility of, 235 use of supplemental by mountain climbers, 208mn, 209 vital role for life, 192 Oxygen anion, 80t Oxygen debt, 755 Oxytocin, 655–656, 656f Ozone formation from oxygen, 105, 138, 138mn resonance structures, 104–105 vital role for life, 192 Ozone layer, 105, 105f, 439–440, 439f, 440mn P Pacemaker, 152–153, 153f Padimate O, 406 PAH (polycyclic aromatic hydrocarbon), 406 Pain relievers, 460, 513 Palladium catalyst, 171, 173f, 392–393, 409, 484, 622 Palm oil, 578t, 579, 584 Palmitic acid, 389, 572, 573mn, 573t, 575 Palmitoleic acid, 389, 573t Pantothenic acid, 732 Para- (prefix), 403–404 Parent name, 363 Parkinson’s disease, 330, 461, 461f Partial hydrogenation, 396–398, 397f Partial pressure Dalton’s law, 208–210 definition, 208 Parts per million (ppm), 239–240 p block, 55–56, 56f PCBs, 344–345 PCR (polymerase chain reaction), 707–708 Peanut butter, 397mn Penicillamine, 454–455 Penicillin, 503f, 532, 532mn, 672 Penta- (prefix), 107t Pentanal, 476 Pentanamine, 544 Pentane boiling point, 371, 479 structure, 359, 359t 2,3-Pentanediol, 464–465 Pentanone, 478 Pentene, 383 Pentose, 611 Pentyl butanoate, 513–514 Pepsin, 667, 720, 722f Peptide definition, 651 dipeptides, 651–654 hormones, 655–656, 656f, 657f neuropeptides, 654–655 tripeptides, 654 Peptide bonds, 651 Percent concentration as conversion factor, 238–239 parts per million (ppm), 239–240 volume/volume, 237–238, 238mn weight/volume, 236–237, 237mn Percent yield calculating, 144–148 from grams of reactant, 145–147 definition, 144 importance in the pharmaceutical industry, 147–148 Period, definition, 44 Period elements, electronic configuration of, 52–53, 54t, 57t Period elements, electronic configuration of, 53–54, 54t, 57t Period elements, electronic configuration of, 57t Periodic table basic features, 44–45, 45f covalent bonding and, 95–96 definition, 34 electronegativity trends, 110–111, 111f electronic configuration, 55–58, 56f Group 1A (alkali metals), 46 Group 2A (alkaline earth elements), 46 Group 7A (halogens), 46–47 Group 8A (noble gases), 46–47 history of, 44 illustration of, 35f, 45f influence on bonding, 67 metalloids, 34, 35f metals, 34, 35f nonmetals, 34, 35f Periodic trends atomic size, 59–60 bond dissociation energy and, 164 definition, 59 electronegativity, 110–111, 111f ionization energy, 60 Peripheral proteins, 590 PET (positron emission tomography), 305, 313–314, 314f Petroleum, 355f, 370–371, 370f, 371mn PGE1, 599 PGE2, 600 PGF2α, 513, 599 pH blood, 292–293 of body fluids, 280, 280f buffers, 287–293, 288f, 289t calculating, 276–280 of buffer, 290–291 with calculator, 279–280 from known [H3O+], A-5 calculating [H3O+] from a known pH, A-5–A-6 of common substances, 278f measuring, 277, 277f pH meter, 277, 277f 12/22/08 4:57:18 PM I-20 pH paper, 277, 277f pH scale, 276–280, 278f Phase change gas to liquid, 221 gas to solid, 221–222 liquid to gas, 220–221 liquid to solid, 219 solid to gas, 221–222, 222mn solid to liquid, 219–220, 220mn Phenanthrene, 404–405 Phenol(s) as antioxidants, 407–408 bond angles, 330 in sore throat spray, 237 Phenolphthalein, 285f Phenylalanine, 459f, 629 Phenylephrine, 555, 556, 561, 562 2-Phenylethylamine, 560 Phenylketonuria, 629, 705t Pheromone, 356, 387mn, 522, 523f Phosphate ion in buffers, 289t as polyatomic ion, 84, 85t Phosphatidylcholine, 585 Phosphatidylethanolamine, 585 Phosphoacylglycerol (phosphoglyceride) structure, 585–586, 586f triacylglycerols and sphingomyelins compared, 584, 588f Phosphodiester, 585, 587, 688, 688mn, 689, 695 Phosphoenolpyruvate, 726, 727, 751, 752f Phosphofructokinase, 746, 749f 2-Phosphoglycerate, 752f 3-Phosphoglycerate, 747, 751, 752f Phosphoglycerate kinase, 747, 752f Phosphoglycerate mutase, 752f Phosphohexose isomerase, 749f Phospholipids in cell membranes, 589–590, 590f definition, 584 phosphoacylglycerols, 584, 585–586, 586f, 588f sphingomyelins, 584, 586–587, 588f Phosphoric acid acid dissociation constant, 272t acid strength, 267t as Brønsted–Lowry acid, 260 exception to octet rule, 102 fertilizer from, 129mn formation of, 129 structure, 585 Phosphorus beta emission of phosphorus-32, 304–305 decay of phosphorus-32, 307–308, 308t exceptions to octet rule, 102 as major mineral (macronutrient), 34, 36f polyatomic anions containing, 85t Phosphorus trichloride, 102 Phosphorylation, 724, 725–727, 726f, 736 oxidative, 737–738 smi26573_EM05_index.indd I-20 INDEX Photosynthesis, 165, 165mn, 610 Physical change definition, 4, 122 separation of mixture components by, Physical properties definition, of ionic compounds, 83 mixture, pure substance, Piperidine, 541, 545 Piperitone, 475 Plasmids, 706, 706f Platinum, as catalyst, 173f β-Pleated sheet, 659, 659f, 660, 660f Point mutation, 703–704 Polar bond in acyl compounds, 505 in carbonyl group, 474, 478 description, 111–114, 341–343 electronegativity difference, 112, 112t in lipids, 570 Polar molecules aldehydes and ketones, 474, 478 definition, 113 dipole–dipole interactions, 211 examples, 113f overview, 341–343 solubility, 231, 232, 343 Polarity bond, 111–114, 112t molecule, 111–114, 113f of organic compounds, 340–343 Pollutants, 344–345 Poly(vinyl acetate), 400 Polyacrylonitrile, 399f Polyamide, 528–529 Polyatomic ion in Brønsted–Lowry acid, 260 covalent bonding within, 84 definition, 83–84 in health and medicine, 87 Lewis structure, 103 naming ionic compounds with, 86–87 naming ions, 84, 85t writing ionic compound formulas, 85–86 Polycyclic aromatic hydrocarbon (PAH), 406 Polyester, 529–531 Polyethylene, 336, 336mn, 398–399, 399mn Polyethylene terephthalate (PET), 401, 401t, 529–531, 530f Polyisobutylene, 399f Polymer, 398–401 condensation, 528–529 natural fibers, 528 polyamide, 528–529, 528mn polyester, 529–531 recycling, 401, 401t, 531, 531mn synthetic, 398–401, 399f, 400t, 401t Polymerase chain reaction (PCR), 707–708 Polymerization, 399 Polynucleotide, 688 See also DNA; RNA Polypeptide, 651 Polypropylene, 400t, 401t Poly(vinyl chloride) PVC, 399f, 400t, 401t Polysaccharide cellulose, 630, 631–632, 631f glycogen, 630, 631, 633–634, 633f starch, 630, 631, 632, 633f structure, 609–610, 630–631 Polystyrene, 399f, 401t Polysubstituted benzenes, 404 Polytetrafluoroethylene, 400t Polyunsaturated triacylglycerols, 577, 578t Poppy, 550, 550mn p orbital energy, 49, 51, 52t in fourth shell, 50, 50t in second shell, 50, 50t shape, 51 in third shell, 50, 50t Positron (β+) definition, 301 positron emission, 305–306 properties, 301t Positron emission, 305–306 Positron emission tomography (PET), 305, 313–314, 314f Postsynaptic neuron, 556, 557f Potassium as alkali metal, 46 definition, 46 as major mineral (macronutrient), 34, 36f potassium-40, 308t role in human body, 74, 74f Potassium cation in electrolyte replacement beverages, 78mn role in human body, 78mn Potassium chloride, 78 Potassium dichromate, 428, 482, 482mn, 483 Potassium iodide, 78 Potassium propanoate, 517 Potassium sorbate, 517 Potential energy, 160 Pounds per square inch (psi), 193 Power plant, nuclear, 315–316, 315f Prednisone, 596 Prefix, 9, 9t, 107t, 363 Preservatives, 517 Pressure atmospheric, 193, 193f, 209 blood, 194–195, 194f changes and effect on equilibrium, 181–182, 183t definition, 193 gas laws Boyle’s law, 195–197, 197f, 202t combined, 201–202, 202t Dalton’s law, 208–210 Gay–Lussac’s law, 200–201, 202t ideal, 206–208 12/22/08 4:57:18 PM INDEX measurement barometer, 193, 193f units, 193 solubility and, 235, 236f Pressure cooker, 201, 201mn Presynaptic neuron, 556, 557f Primary (1°) amine, 541–543, 546–547, 552 Primary (1°) carbon, 360 Primary structure polynucleotide, 688 protein, 657–658, 663f Primers, in PCR, 707–708 Primes ('), 684 Principal energy levels, 49, 50t Problem solving clinical conversion factors, 22–24 factor–label method, 18–22 Products in chemical equations, 123 converting grams of reactant to grams of product, 140–143 converting moles of reactant to grams of product, 138–140 definition, 122 equilibrium constant and, 174–178, 176f Proenzyme, 673–674 Progesterone, 390, 595 Progestins, 595 Propanamine, 544 Propane boiling point, 214 combustion of, 125–126, 125mn, 166–167 melting point, 214 as propellant, 439mn structure, 325, 357, 359t Propanethiol, 441 Propanoic acid, 515–516 1-Propanol, boiling point of, 510 2-Propanol oxidation of, 429 structure, 421, 425f uses, 425f Propellant, aerosol, 439–440, 439mn Propene, 330, 394–395, 400t Propranolol, 460 Propyl acetate, 505 Prostaglandins, 513, 599–600 Protease, 669 Protease inhibitor, 710, 711 Protein synthesis, 700–703, 701f Proteins amino acids (see Amino acids) Calories in, 161–162, 161t in cell membranes, 590 common, 664–667 collagen, 664–665, 664f hemoglobin, 665–667, 666f, 666mn α-keratin, 664, 664f myoglobin, 665–667, 665mn, 666f conjugated, 665 smi26573_EM05_index.indd I-21 I-21 contractile, 645 definition, 645 denaturation, 668–669, 668mn digestion, 720, 721f, 722f enzymes, 669–676 fibrous, 645, 664 globular, 664, 669 in human body, 644, 645, 645f hydrolysis, 667–668 membrane, 644 peptide definition, 651 dipeptides, 651–654 hormones, 655–656, 656f, 657f neuropeptides, 654–655 tripeptides, 654 recommended daily intake, 645, 646t storage, 645 structure, 657–664 primary, 657–658, 663f quaternary, 661, 663f secondary, 658–660, 658f–660f, 663f shorthand synthesis, 659f tertiary, 661, 663f transport, 645 Proton atomic number, 38–39 charge, 37, 38t definition, 259 mass, 37, 38, 38t in mass number, 39 transfer in Brønsted–Lowry acid–base definition, 259–266 Proton donor aspirin as, 519 carboxylic acids as, 515 Proventil, 147, 147f Prozac, 147, 147f Pseudoephedrine, 561, 562 psi (pounds per square inch), 193 Psilocin, 559 Pure substance classification as element or compound, 6, 8f definition, 5, 229 physical properties, Purine, 683–684 Putrescine, 542 Pyrethrin I, 368 Pyridine, 545 Pyrimidine, 683–684 Pyrrole, 545 Pyrrolidine, 545 Pyruvate conversion to acetyl CoA, 754, 758 conversion to ethanol, 756–757 conversion to lactate, 670, 729–730, 755, 756f formation in glycolysis, 751–753, 752f formation from phosphoenolpyruvate, 726, 727 gluconeogenesis, 759–760, 760f Pyruvate decarboxylase, 756 Pyruvate kinase, 752f Pyruvic acid, 487 Q Quaternary ammonium salts, 556 Quaternary (4°) carbon, 360 Quaternary structure, protein, 661, 663f Quinine, 551 R Racemic mixture, 460 Racemic switch, 460 Rad—radiation absorbed dose, 311 Radiation See also Radioactivity background, 310, 311 types of, 300–301, 301t Radioactive decay definition, 302 half-life, 307–309, 308t Radioactivity alpha emissions, 302–303, 302mn beta emissions, 303–305, 304f definition, 299 detecting and measuring, 310–311, 310mn, 310t effects of, 301–302 gamma emission, 306–307, 307f half-life, 307–309, 308t measuring human exposure to, 311 medical uses, 304, 304f, 311–314, 312f–314f beta radiation, 304, 304f gamma radiation, 306–307, 307f iodine-131 for hyperthyroidism in, 304, 304f positron emission tomography (PET), 305, 313–314, 314f positron emission, 305–306 types of radiation, 300–301, 301t Radiocarbon dating, 309, 309f Radioisotope definition, 299 half-life, 307–309, 308t medical uses, 304, 304f, 307, 307f, 311–314, 312f–314f diagnosis, 311–312, 312f, 313–314, 313f, 314f treatment, 312, 313f Radium, 46 Radon, 47, 303 Radon detector, 47, 47mn Reactants calculating percent yield from grams of reactant, 145–147 in chemical equations, 123 converting grams of reactant to grams of product, 140–143 12/22/08 4:57:18 PM I-22 Reactants (continued) converting moles of reactant to grams of product, 138–140 definition, 122 equilibrium constant and, 174–178, 176f Reaction arrow, 266 Reaction coordinate, 168, 169f Reaction rate concentration, effect of, 170 definition, 168 energy of activation, effect of, 168–169, 170 temperature, effect of, 170 Reactions catalysts, 171–173, 171f–173f chemical, 121–153 endothermic, 163, 165–166, 165t energy changes in, 162–167 energy diagram, 167–170, 169f equilibrium constant, 174–178 exothermic, 163, 165–166, 165t Le Châtelier’s principle, 179–182, 183t molecular collisions, 167–168, 170 nuclear (see Nuclear reactions) redox (see Oxidation–reduction (redox) reactions) reversible, 173–174 transition state, 168, 169f understanding biochemical, 745–747 Recombinant DNA, 705–710, 706f Recycling polymers, 401, 401t Red blood cells, osmotic pressure effects, 250, 251f Red tide, 433, 433mn Redox reaction See Oxidation–reduction (redox) reactions Reducing agent, 149, 728–730, 731t, 737, 747 Reducing sugar, 623 Reduction of aldehydes and ketones, 484–487 coenzymes and, 728–730, 731t definition, 148, 728 examples of, 150f of monosaccharides, 621, 622 results of, 152, 372 Refining, 370, 370f Rem—radiation equivalent for man, 311 Replication, 693–695, 694f Replication fork, 693, 694f Resonance structure aromatic compounds, 402 definition, 104, 402 drawing, 103–104 ozone, 104 resonance-stabilized, 104 Respiratory acidosis, 292 Respiratory alkalosis, 293 Restricted rotation, 385 Restriction endonuclease, 706–707, 706f Retinal, 473f, 475, 487–488, 489f 11-cis-retinal, 473f, 475, 487–488, 489f smi26573_EM05_index.indd I-22 INDEX Retinol, 487–488, 489f Retrovirus, 710, 711f Reverse reaction, 174 Reverse transcription, 710, 711, 711f Reversible inhibitor, 672 Reversible reaction, 173–174 Rhodium, as catalyst, 173f Ribbon diagram, 659, 660f Riboflavin, 730, 731, 731mn Ribonucleic acid See RNA Ribonucleotide, 686 Ribose, 611–612, 614, 683, 684 Ribosomal RNA (rRNA), 695–696, 696t, 700 Rickets, 597 Rizatriptan, 559 RNA components, 686t, 687t, 695 function, 682, 683 genetic code, 698–700, 699t messenger (mRNA), 695–698, 696t, 699t, 700, 701f, 701t, 702–704, 702f ribosomal (rRNA), 695–696, 696t, 700 structure, 683 transcription, 693, 697–698, 697f transfer (tRNA), 695–696, 696f, 696t, 700, 701f, 701t, 702, 702f translation, 693 RNA polymerase, 697, 697f Rofecoxib, 600 Roman numeral, use in naming, 79, 79t Rounding off numbers, 14–15, 14t, A-3 Rowland, F Sherwood, 439mn rRNA (ribosomal RNA), 695–696, 696t, 700 RU 486, 391 Rubber, 2, 3f Rubbing alcohol, 238 Rubidium, 46 Rust, 150 S Saccharin, 629, 629t, 630f Salicin, 493, 519 Salicylic acid, 125, 142–143, 512, 519, 522 Saline solution, 229, 229f, 238–239, 241 Salmeterol, 420, 562 Salt solution, acidity and basicity of, 283–284, 284t Salts acidity and basicity of salt solution, 283–284, 284t ammonium, 553–556 of carboxylic acids, 516–517 formation in acid–base reactions, 281–284 metal, 281 zwitterion, 646, 649 Samuelsson, Bengt, 513 Sand, as network solid, 218f, 219 Saponification, 525, 584, 584mn Saponin, 517 Sarin, 673 Saquinavir, 506 Saturated fats (triacylglycerols), 577, 578mn, 578t, 579, 580, 581f Saturated fatty acids, 387–389, 388t, 389f, 397–398, 572–573, 573t Saturated hydrocarbon, 356 See also Acyclic alkanes Saturated solution, 231 s block, 55–56, 56f Scientific calculator calculating pH from a known [H3O+], A-5 converting a number to scientific notation, A-4 entering a number written in scientific notation, A-5 taking the antilogarithm of a number, A-5–A-6 taking the logarithm of a number, A-5 Scientific notation, 16–18, 17t, 130, A-1–A-2 Scuba diver, 209, 235 Seawater, pH, 279mn Second (unit of measurement), 9t Secondary (2°) amine, 541–544, 546, 552 Secondary (2°) carbon, 360 Secondary structure, proteins, 658–660, 658f–660f, 663f Selective serotonin reuptake inhibitor (SSRI), 559 Selenium, as trace element (micronutrient), 34, 36f Semiconservative replication, 693 Semipermeable membrane, 248–251, 252f Sense of smell, 465–466, 466f Serine, 651, 768 Serotonin, 557, 558–559 Sertraline, 559 Sex hormones, 595 Shape of molecules See Molecular shape Shell definition, 49 electron distribution, 49–50, 50t valence, 56 SI units, 8mn Sickle cell anemia, 666–667, 666mn, 705t Sickle cell hemoglobin, 666 Side chain, amino acid, 646 Side reaction, 143 Sievert (Sv), 311 Significant figures in addition and subtraction, 15–16, A-4 definition, 12, A-2 determining number of, 12–13, A-3–A-4 exact and inexact numbers, 11–12 in multiplication and division, 13–15, A-4 rounding off, 14–15, 14t, A-3 Silent mutation, 704 Silicon, as trace element (micronutrient), 36f Silicon dioxide, as network solid, 218f, 219 Silkworm moth (Bombyx mori), 386, 387mn, 528 Silver(I) oxide, 482 1/5/10 3:21:05 PM INDEX Simvastatin, 594 Skeletal structure alkanes, 361–362 description, 333–334 Skin care products, 512, 512mn Smell, sense of, 465–466, 466f Smoke detector, 302mn, 303 Soap, 517–519, 518f, 518mn, 583–584 Sodium as alkali metal, 46 definition, 46 dietary, 75, 75t as major mineral (macronutrient), 34, 36f role in human body, 74, 74f Sodium acetate, 287, 515, 517 Sodium alendronate, 87 Sodium azide, 128, 128f Sodium benzoate, 517 Sodium bicarbonate in acid–base reaction, 282–283 antacid, 282 dissolved in water, 284 naming, 86 use in medicine, 87 Sodium carbonate, 259 Sodium cation, formation of, 68–69 Sodium chloride aqueous solution, 229–230, 229f, 238–239, 241 as compound, 6, 7f dissolution in water, 84f, 231–232, 231f, 284 as electrolyte, 230 formation of, 281 formula weight, 132 ionic bonding, 67 as ionic compound, 75–76 as ionic solid, 218, 218f molar mass, 133 mole of, 130mn, 140f osmotic pressure of solution, 249–250 properties, 341f Sodium fluoride, 78, 80 Sodium hydroxide acid–base titration with, 285–287, 285f as Arrhenius acid, 259 as Brønsted–Lowry base, 262f dissociation, 276 reaction with hydrochloric acid, 281 solution, 241 as strong base, 269f Sodium iodide, 68, 311 Sodium nitrite, 85, 85mn Sodium octanoate, 516 Sodium oleate, 584 Sodium salicylate, 519 Sodium stearate, 583 Soft drink, carbonated, 235, 236f Solid amorphous, 218, 219, 219mn crystalline, 218–219, 219f smi26573_EM05_index.indd I-23 I-23 definition, 3, 191 melting point, 213–214 mixtures, 6, 7f phase changes gas to solid, 221–222 liquid to solid, 219 solid to gas, 221–222, 222mn solid to liquid, 219–220, 220mn properties, 191, 192t Solubility alcohols, 421–422 aldehydes and ketones, 479 amides, 511 amines, 546, 554 basic principles, 231–233 carboxylic acids, 511 definition, 231 of environmental pollutants, 344–345 enzyme, 669 esters, 511 gas, 235, 236f ionic compounds, 83, 231–232, 231f, 234–235 “like dissolves like” concept, 231, 233, 343, 421, 479 lipids, 570 monosaccharide, 612 nonpolar covalent compounds, 231, 232–233, 233f organic compounds, 343–344, 344t polar covalent compounds, 231, 232 pressure effects, 235, 236f temperature effects, 235 vitamins, 345–346, 347f in water, 231–235, 231f Solute definition, 229 nonvolatile, 246–247, 246f volatile, 246–247, 246f Solution, 228–252 aqueous, 229–230 colligative properties, 246–248 boiling point elevation, 246–247, 246f freezing point depression, 247–248 colloids compared, 229 concentration, 236–246 dilution, 244–246 making solution with particular concentration, 237f molarity, 241–244 parts per million (ppm), 239–240 percent concentration as conversion factor, 238–239 volume/volume percent, 237–238, 238mn weight/volume percent, 236–237, 237mn definition, 228 dialysis and, 251, 252f dilution, 244–246 electrical conductivity in, 230 as homogeneous mixture, 229 hypertonic, 250, 251f hypotonic, 250, 251f isotonic, 250, 251, 251f osmosis, 248–251, 251f saturated, 231 solubility, 231–236 supersaturated, 235 types, 230f unsaturated, 231 Solvation definition, 232 energy release, 233 Solvent definition, 229 freezing point depression, 247–248 organic, 343 Sorbitol, 570–571, 622, 622mn, 629t s orbital energy, 49, 51, 52t in first shell, 49, 50t in fourth shell, 50, 50t in second shell, 50, 50t shape, 51 in third shell, 50, 50t Space-filling representation, 37 Spam, 85mn Specific gravity, 27 Spectator ion, 281 Spermaceti wax, 575, 575mn, 576 Spermine, 542 SPF rating (sun protection factor), 406mn Sphingomyelin myelin sheath, 587, 588f structure, 586–587 triacylglycerols and phosphoacylglycerols compared, 584, 588f Sphingosine, 586–587 Sphygmomanometer, 194, 194f Spider dragline silk, 660, 660f Spin, electron, 49mn, 52 Spiral pathway, 762 Sports drink, 228f SSRI (selective serotonin reuptake inhibitor), 559 Stahl, Franklin, 693 Standard conditions of temperature and pressure (STP), 204 Standard molar volume, 204 Stannic ion, 79t Stannous fluoride, 82, 82mn Stannous ion, 79t Stanozolol, 595 Starch amylopectin, 632, 633f amylose, 632, 633f digestion, 722f in foods, 609 glycosidic linkages, 630, 631, 632 hydrolysis, 426, 632 hydroxyl groups in, 425, 632 structure, 425, 610 12/22/08 4:57:19 PM I-24 States of matter See also Gas; Liquid; Solid changes in, 4–5 definition, 3, 191 examples, 191f properties, 192t of water, 4, 4f, Statins, 594 Stearic acid, 232, 388, 388t, 389f, 396, 572–573, 573t, 761, 764–765 Stereochemistry, 449–466 of amino acids, 647 constitutional isomers compared, 387, 387f definition, 387, 449 Stereoisomers See also Chirality center cis–trans, 385–387, 387f, 451 definition, 387, 450 diastereomers, 464–465 enantiomers, 453 amino acids, 647–648 definition, 456 dopa, 461 drawing pair of, 456–457 glucose, 613–614 glyceraldehyde, 612–613 interaction with chiral receptor, 459, 459f odor molecules, 466 pain relievers, 460 racemic mixture, 460 of thalidomide, 458, 458mn structure, 450 Sterling silver, 77, 78mn Steroid cholesterol, 591–594, 592t, 593f, 594f hormones, 595–596 structure, 591 Sticky ends, 706 Stone, Reverend Edmund, 519 Stop codon, 699, 699t STP (standard conditions of temperature and pressure), 204 Straight-chain alkane, 357, 359t Strong acid acid dissociation constant, 272 conjugate base of, 269 conjugate bases of, 267t definition, 266 dissolution in water, 266, 268f examples of common, 266–267, 267t salt formation, 283–284, 284t Strong base conjugate acid of, 269 definition, 268 dissolved in water, 268–269, 269f salt formation, 283–284, 284t Strontium, 46 Sublimation, 221–222 Subshells, 49 Substituents definition, 363 naming, 363–364 Substitution mutation, 703 smi26573_EM05_index.indd I-24 INDEX Substitution reaction amide formation, 521, 523–524 chlorination, 409 definition, 408 ester formation, 521–522 nitration, 409–410 sulfonation, 410–411 Subtraction, using significant figures in, 15–16, A-4 Subunit, protein, 661 Succinate, 734, 734f, 735 Succinate dehydrogenase, 734 Succinyl CoA, 733, 734f Sucralose, 629, 629t, 630f Sucrose, 629, 629t Suffix, 363 Sugar alcohol, 622 Sugars See Carbohydrates Sulfa drugs, 410 Sulfamethoxazole, 410 Sulfanilamide, 410, 673 Sulfate ion, 84, 85t Sulfhydryl group in coenzyme A, 731 in thiols, 419, 440–442 Sulfide anion, 80t Sulfisoxazole, 410 Sulfite ion, 85t Sulfonation, 410–411 Sulfur in coal, 55mn exceptions to octet rule, 102 in fossil fuels, 105 as major mineral (macronutrient), 34, 36f polyatomic anions containing, 85t thiols, 440–442 Sulfur anion, 80t Sulfur dioxide, 105 Sulfur trioxide, 410–411 Sulfuric acid acetal formation, 489–490 acid rain, 283, 286, 287mn, 291, 291f acid strength, 266, 267t as Brønsted–Lowry acid, 260 exception to octet rule, 102 industrial use, 267 reaction with sodium bicarbonate, 283 titration, 286–287 Sumatriptan, 559 Sunscreens, 405, 406mn, 480 Supercoil, 664, 664f Superhelix, 664 Supersaturated solution, 235 Surface tension, 217–218, 218f Sutures, dissolving, 530–531 Sweetener, artificial, 629, 629t, 630t Sweetness, 629, 629t, 630f Symbols in chemical equations, 124t element, 33, 33t Synapse, 556, 557f Synthetic materials, 2, 2f, 3f Systematic name, 362–363, 543 Systolic pressure, 194, 194f T Table sugar See also Sucrose density, 25t mole of, 140f Tamiflu, 148, 339–340 Tamoxifen, 390 Tanning agents, 480 Taq polymerase, 708 Tarnish, 77, 78mn Tartaric acid, 455, 512 Taxol, 2, 3f, 419–420 Tay–Sachs disease, 705t Tea, 547, 548t Technetium-99, 306, 306mn, 308t, 311–312, 312f Temperature changes and effect on equilibrium, 180–181, 183t definition, 24 effect on density, 25 gas laws Charles’s law, 197–199, 199f, 202t Gay–Lussac’s law, 200–201, 202t ideal, 206–208 human body, 182–184, 183f reaction rate and, 170 scales, 24–25, 24f solubility and, 235 Template strand, 697, 698 Terephthalic acid, 529, 530, 531 Termination, stage of translation, 701, 701f, 702 Tertiary (3°) amine, 541–544, 546–547, 552, 555 Tertiary (3°) carbon, 360 Tertiary structure, protein, 661, 663f Testosterone, 595 Tetra- (prefix), 107t Tetrafluoroethylene, 400t Tetrahedral carbon, 357 Tetrahedral shape, 107, 108, 109t, 327–328, 329t, 343 Tetrahydrocannabinol (THC), 336 Tetrahydrogestrinone, 595 Tetrose, 611 Thalidomide, 458, 458mn Thallium-201, 312 Theoretical yield definition, 143, 143mn in percent yield calculations, 144–147 Thermal cycler, 708 Thermometer, 24mn Thermoregulation, 183–184, 183f Thioester, 731–732, 733 Thiol coenzyme A, 731–732 definition, 419 -thiol (suffix), 440–441 12/22/08 4:57:19 PM INDEX Threonine, 463–464 Threose, 612, 624 Thymine, 683–684, 691 Thyroid gland, 43, 44f Tidal volume, 206f Time, units of measurement, 9t Tin cation, 79t Tin(II) fluoride, 82 Tin(IV) oxide, 82–83 Titration, 285–287, 285f Tobacco, 540f, 549, 549f Tollens reagent, 482, 483, 484 Tollens test, 482mn Torr, 193, 193mn Torricelli, Evangelista, 193mn Trace element, 34, 36f Trade name, 362–363 Trans fats (trans triacylglycerols), 397–398, 578t, 580, 581f Trans isomer, 385–387, 387f, 451 Transaminase, 767, 768 Transamination, 767–768 Transcription, 693, 697–698, 697f Transfer RNA (tRNA), 695–696, 696f, 696t, 700, 701f, 701t, 702, 702f Transition metal elements cations, 73, 73t in periodic table, 44, 45f Transition state, 168, 169f Translation, 693, 700–703, 701f Transport across a cell membrane, 590–591, 591f Tri- (prefix), 107t Triacylglycerols, 527, 576–584 catabolism, 760–765 fatty acid, 761–765, 763f glycerol, 761 definition, 576 in diet, 579–580, 580mn, 581f digestion, 720, 721f, 722f fatty acid composition of common, 577–578, 578t hydrolysis, 580–582, 584 metabolism of, 582–583, 582f monounsaturated, 577 phospholipids compared, 584, 588f physical properties, 577 polyunsaturated, 577 soap synthesis, 583–584 structure, 570, 577 Tricarboxylic acid cycle (TCA cycle) See Citric acid cycle Trichloromethane, 438 Triethylamine, 543, 554 Triglycerides See Triacylglycerols Trigonal planar carbon, 380 Trigonal planar geometry, 657 Trigonal planar shape, 107, 108, 109t, 329t Trigonal pyramidal shape, 109, 109t, 328, 329t Trimethylamine, 541, 545 smi26573_EM05_index.indd I-25 I-25 Triol, 423 Triolein, 584 Triose, 611 Triose phosphate isomerase, 747, 750f Tripeptide, 651 Triple bond alkynes, 380 definition, 100, 325 Lewis structure, 100 Triple helix, of collagen, 664, 665f Triprotic acid, 260 Tristearin, 580, 583 Tritium (T), 41, 316 tRNA See Transfer RNA (tRNA) Trypsin, 667, 674, 720 Trypsinogen, 674 Tryptophan, 558 Tylenol, 22, 23, 93f, 145 Tyrosine, 558f, 654 U Undecane, 356 Units of measurement conversion factors, 19–24 English system, 8, 12t metric system, 8–10, 9t, 11t, 12t for pressure, 193 SI, 8mn Universal gas constant (R), 206–208 Unpaired electron, 52 Unsaturated fats (triacylglycerols), 578, 578t, 579, 580, 581f Unsaturated fatty acids, 387–389, 388t, 389f, 396–398, 397f, 572–574, 573t Unsaturated hydrocarbons, 379–411 See also Alkenes; Alkynes aromatic compounds, 402–411 definition, 380 fatty acids, 387–389, 388t, 389f, 396–398, 397f isomers, 385–387, 387f polymers, 398–401, 399f, 400t, 401t Unsaturated solution, 231 Uracil, 683–684 Uranium-235, 308, 308t, 315 Uranium-238, decay of, 302 Urea, 768 Urine, 25t, 27 Urushiol, 407–408 V Vaccine, 710, 710mn Valdecoxib, 600 Valence electron configurations of main group elements, 57t definition, 56 in electron-dot symbol, 58–59 identifying, 56–58 in Lewis structure, 95, 97, 98 Valence shell, 56 Valence shell electron pair repulsion (VSEPR) theory, 107, 327 Valine, 653, 768 van der Waals forces, 210mn See also London dispersion forces Vane, John, 513 Vanillin, 407, 481f Vapor, 215 Vapor pressure above a liquid solution, 246–247, 246f boiling point elevation, 246–247 definition, 215 intermolecular forces and, 215–216 Vaporization definition, 220 heat of, 220–221 Vasopressin, 655, 656, 657f Vegetable oils, 396–398, 397f, 397mn Ventolin, 147, 147f Vesicle, 556, 557f Vinegar, 236, 261f, 268f Vinyl chloride, 400t Virus, 710–711, 711f Viscosity, 217–218 Vision, chemistry of, 487–488, 489f Vitamins A, 322, 345–346, 345mn, 347f, 488, 597, 597t B2, 730, 731, 731mn B5, 732 C, 68, 346, 346mn, 347f, 665 D, 368, 597–598, 597t definition, 345, 597 E, 408, 408mn, 570, 597t, 598 fat-soluble, 345, 597–599, 597f K, 456, 456mn, 597t, 598 origin of term, 345mn water-soluble, 345 Volatile solute, 246–247 Volcano, 99mn Volume dilution of solutions, 244–246 gas laws Avogadro’s law, 202–206 Boyle’s law, 195–197, 197f, 202t Charles’s law, 197–199, 199f, 202t combined, 201–202, 202t ideal, 206–208 measuring, 10–11 units of measurement, 9t, 10–11, 11t, 12t Volumetric flask, 236, 237f Volume/volume percent concentration (v/v)%, 237–238, 238mn von Baeyer, Adolf, 362 VSEPR (valence shell electron pair repulsion) theory, 107, 327 Vulcanization, 2, 3f 12/22/08 4:57:19 PM I-26 W Water as acid, 265, 267t acid dissolved in, 266, 268, 268f as base, 265, 268t, 272 base dissolved in, 268–269, 268f boiling point, 213–214 as Brønsted–Lowry base, 259, 262 cardiovascular system and, 97, 97f changes in state, as compound, 6, 7f covalent bonding, 95 density, 25–26, 25t dipoles, 113–114 dissociation, 274–276 formation from strong acid and strong base, 281 heat of vaporization, 221 hydration, 395–396 ice, 218–219, 218f, 220 intermolecular forces, 213–214, 216, 217 Lewis structure, 106, 109 melting point, 213–214 molar mass, 134 mole of, 130mn, 140f molecular shape, 109 osmosis, 248–250 as polar molecule, 113–114 smi26573_EM05_index.indd I-26 INDEX removal by sublimation, 222mn as solvent, 231–235 states of matter, 4, 4f, surface tension, 217, 218f vapor pressure, 216 viscosity, 217 Water-soluble vitamin, 345, 346, 347f Watson, James, 690 Wax, 575–576, 575mn Weak acid acid dissociation constant, 272, 272t of buffer, 287, 289, 289t conjugate base of, 367t definition, 266 dissolution in water, 268f, 368 examples of common, 268 salt formation, 283–284, 284t Weak base definition, 268 dissolved in water, 268–269, 269f salt formation, 283–284, 284t Weight, 10 Weight/volume percent concentration (w/v)%, 236–237, 237mn Willow tree, 519, 519mn Wind currents, Charles’s law and, 199, 199f Wine, 139, 139mn, 757 Wool, 528 X Xenon, 47 Xenon-133, 311 X-rays, 317, 317f Xylitol, 622 Xylose, 622 Y Yew tree, 2, 3f -yl (suffix), 363–364, 435, 507, 652, 654 -yne (suffix), 382, 384 Z Zaitsev rule, 427 Zero absolute, 24 as significant figure, 13 Zileuton, 601 Zinc in batteries, 151, 151f metal reaction with copper cations, 148–149, 149f as trace element (micronutrient), 34, 36f Zinc oxide, 66f, 78 Zwitterion, 646, 649 Zymogen, 673–674 12/22/08 4:57:19 PM smi26573_endpapers_front.indd 12/8/08 3:06:54 PM 5B 6B 7B 8B 10 1B 11 2B 12 Ti Zr 57 La Ac (227) Ra (226) Fr (223) 89 88 87 72 Mn 25 41 Nb 73 Ta 42 W 74 95.94 Mo 43 Re 75 (98) Tc (267) Rf 104 Fe 26 Co 27 Ni 28 76 Pa Th U 92 232.0381 231.03588 238.0289 91 46 Pd 47 Ag Cd 48 65.41 Zn 30 N O 6A 16 14 Si P 15 S 16 In 49 69.723 Ga Sn 50 72.64 Ge 32 Sb 51 74.9216 As 33 Te 52 78.96 Se 34 26.9815 28.0855 30.9738 32.066 31 F 7A 17 Ne 10 4.0026 He I 53 79.904 Br 35 35.453 Cl 17 Xe 54 83.80 Kr 36 39.948 Ar 18 12.011 14.0067 15.9994 18.9984 20.1797 C 5A 15 78 79 Au 80 Hg 81 Tl Eu 63 (281) Ds 110 Gd 64 (280) Rg 111 Tb 65 (285) – 112 Dy 66 195.08 196.9665 200.59 204.3833 Pt 82 Ho 67 (289) – 114 207.2 Pb 83 Er 68 208.9804 Bi 84 Tm 69 (293) – 116 (209) Po 85 Yb 70 (210) At 86 Lu 71 (222) Rn Pu (244) Np 94 96 (243) (247) Am Cm 95 (247) Bk 97 (251) Cf 98 (252) Es 99 (257) Fm 100 (258) Md 101 (259) No 102 (262) Lr 103 150.36 151.964 157.25 158.9253 162.50 164.9303 167.26 168.9342 173.04 174.967 Sm 62 (276) Mt 109 192.22 Ir 77 (237) 93 (145) 61 (270) Hs 108 190.2 Os 140.115 140.9076 144.24 90 45 Rh 63.546 Cu 29 Al B 4A 14 8A 18 101.07 102.9055 106.42 107.8682 112.411 114.82 118.710 121.760 127.60 126.9045 131.29 Pm 60 44 Ru Nd 59 Pr 58 Ce Bh 107 (272 ) Sg 106 (271) (268) Db 105 178.49 180.9479 183.84 186.207 Hf Cr 24 50.9415 51.9961 54.9380 55.845 58.9332 58.693 V 23 88.9059 91.224 92.9064 Y 39 132.9054 137.327 138.9055 56 Ba 55 87.62 85.4678 Cs 38 Sr 37 Rb 40 Sc 22 47.88 Ca K 21 39.0983 40.078 44.9559 20 19 22.9898 24.3050 11 Na 4B 13 12 Mg Li 6.941 3B 10.811 Be 9.0122 1.0079 3A 13 Periodic Table of the Elements 2A H 1A 7 THE ELEMENTS Element Symbol 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 Meitnerium Mendelevium 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 Mt Md Atomic Number Relative Atomic Mass* 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 25 109 101 (227) 26.9815 (243) 121.760 39.948 74.9216 (210) 137.327 (247) 9.0122 208.9804 (272) 10.811 79.904 112.411 40.078 (251) 12.011 140.115 132.9054 35.453 51.9961 58.9332 63.546 (247) (281) (268) 162.50 (252) 167.26 151.964 (257) 18.9984 (223) 157.25 69.723 72.64 196.9665 178.49 (270) 4.0026 164.9303 1.0079 114.82 126.9045 192.22 55.845 83.80 138.9055 (262) 207.2 6.941 174.967 24.3050 54.9380 (276) (258) Element Symbol 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 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 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 40 112** 114 116 Relative Atomic Mass* 200.59 95.94 144.24 20.1797 (237) 58.693 92.9064 14.0067 (259) 190.2 15.9994 106.42 30.9738 195.08 (244) (209) 39.0983 140.9076 (145) 231.03588 (226) (222) 186.207 102.9055 (280) 85.4678 101.07 (267) 150.36 44.9559 (271) 78.96 28.0855 107.8682 22.9898 87.62 32.066 180.9479 (98) 127.60 158.9253 204.3833 232.0381 168.9342 118.710 47.88 183.84 238.0289 50.9415 131.29 173.04 88.9059 65.41 91.224 (285) (289) (293) *Values in parentheses represent the mass number of the most stable isotope **The names and symbols for elements 112, 114, and 116 have not been chosen smi26573_endpapers_front.indd 12/8/08 3:06:55 PM Common Functional Groups in Organic Chemistry Type of Compound General Structure Alcohol R R O O C C R H CH3 C C R X (X = F, Cl, Br, I) C Alkyne H C O Amide R C –X Br H triple bond NH2 –CONH2, –CONHR, –CONR2 C O N H (or R) H (or R) Amine double bond C CH3 H C –– H H Alkyl halide C O carbonyl group CH3CH3 H C –OH hydroxyl group H H Alkene Functional Group OH CH3 OH Aldehyde Alkane Example R NH2 or R2NH or R3N CH3 C CH3 NH2 Aromatic compound Carboxylic acid benzene ring O O R C OH CH3 R R C O OR CH3 R CH3 R smi26573_endpapers_back.indd C OH C –COOH carboxyl group O –COOR OCH3 CH3 O O Ketone C O O Ester Ether –NH2 amino group R CH3 C CH3 –OR C O carbonyl group 12/8/08 3:18:46 PM Common Metric Prefixes Prefix Symbol Numerical Value mega- M 106 kilo- k 103 deci- d 10–1 centi- c 10–2 milli- m 10–3 micro- µ 10–6 nano n 10–9 Useful Conversion Factors Length Mass Volume m = 100 cm = 1,000 mm kg = 1,000 g L = 1,000 mL cm = 10 mm g = 1,000 mg mL = cm3 = cc 2.54 cm = in kg = 2.21 lb 946 mL = qt m = 39.4 in 454 g = lb L = 1.06 qt km = 0.621 mi 28.4 g = oz 29.6 mL = fl oz Temperature Pressure Energy °F = 1.8(°C) + 32 atm = 14.7 psi kcal = 1,000 cal °C = (°F – 32)/1.8 atm = 760 mm Hg cal = 4.184 J K = °C + 273 mm Hg = torr Physical Constants smi26573_endpapers_back.indd Avogadro’s number 6.02 × 1023 particles/mol Universal gas constant (R) 0.0821 L · atm/mol · K Universal gas constant (R) 62.4 L · mm Hg/mol · K Volume of one mole of gas at STP 22.4 L 12/8/08 3:18:46 PM Front Cover: Cholesterol (C27H46O) is a well-known molecule synthesized in the liver and found in almost all body tissues While cholesterol is a necessary component of healthy cell membranes, high blood cholesterol levels are associated with an increased risk of developing coronary artery disease, heart attack, and stroke Since cholesterol is insoluble in the blood, it is transported throughout the body in water-soluble particles called HDLs and LDLs An understanding of the interplay of cholesterol, HDLs, and LDLs in the overall health of an individual begins with a basic knowledge of the structure and properties of these key compounds Student Study Guide/Solutions Manual (ISBN: 0-07-302658-1; ISBN-13: 978-0-07-302658-9) The Student Study Guide/Solutions Manual, prepared by Erin Smith and Janice Gorzynski Smith, begins each chapter with a detailed chapter review organized around the chapter goals and key concepts The Problem Solving section provides a number of examples for solving each type of problem essential to that chapter The Self-Test section of each chapter quizzes chapter highlights, with answers provided Finally, each chapter ends with the solutions to all in-chapter problems, as well as the solutions to all odd-numbered end-of-chapter problems Connect Electronic Homework and Assessment System www.mcgrawhillconnect.com/chemistry MD DALIM #1000127 12/19/08 CYAN MAG YEL BLK SPOTUV McGraw-Hill’s unique homework and assessment system, known as Connect, is an electronic homework and course management system designed for greater flexibility, power, and ease of use than any other system Connect is ideal for preplanned assignments, and is also fully customizable to fit specific course needs Build Assignments Choose from pre-built assignments or create your own using resources within Connect Track Student Progress Assignments are automatically graded An electronic grade book provides reports on progress Share Course Materials Instructors can create and share materials with colleagues Want to learn more? Find your McGraw-Hill representative at www.mhhe.com ISBN 978-0-07-302657-2 MHID 0-07-302657-3 Part of ISBN 978-0-07-727429-0 MHID 0-07-727429-6 www.mhhe.com ... Mānoa, where she teaches a one-semester organic and biological chemistry course for nursing students, as well as the two-semester organic chemistry lecture and lab courses She also serves as the... to Organic Molecules and Functional Groups 322 11.1 11.2 11.3 11.4 Introduction to Organic Chemistry 323 Characteristic Features of Organic Compounds Shapes of Organic Molecules 327 Drawing Organic. .. focus on learning major concepts and themes of general, organic, and biological chemistry Relevant materials from everyday life are used to illustrate concepts, and topics are broken into small