E i g h T h E d i T i o n Chemistry for Today General, Organic, and Biochemistry Spencer L. Seager Weber State University Michael R. Slabaugh Weber State University Australia • Brazil • Japan • Korea • Mexico • Singapore • Spain • United Kingdom • United States UUnnlleessss ootthheerrwwiissee nnootteedd aallll aarrtt oonn tthhiiss ppaaggee ©© CCeennggaaggee LLeeaarrnniinngg 22001144 Copyright 2012 Cengage Learning. All Rights Reserved. May not be copied, scanned, or duplicated, in whole or in part. Due to electronic rights, some third party content may be suppressed from the eBook and/or eChapter(s). Editorial review has deemed that any suppressed content does not materially affect the overall learning experience. Cengage Learning reserves the right to remove additional content at any time if subsequent rights restrictions require it. 02279_FM_ptg01_hr_pi-xxxi.indd 1 9/7/12 5:30 PM This is an electronic version of the print textbook. 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To learn more about Brooks/Cole, visit www.cengage.com/brookscole Purchase any of our products at your local college store or at our preferred online store www.cengagebrain.com. Printed in the United States of America 1 2 3 4 5 6 7 16 15 14 13 12 UUnnlleessss ootthheerrwwiissee nnootteedd aallll aarrtt oonn tthhiiss ppaaggee ©© CCeennggaaggee LLeeaarrnniinngg 22001144 Copyright 2012 Cengage Learning. All Rights Reserved. May not be copied, scanned, or duplicated, in whole or in part. Due to electronic rights, some third party content may be suppressed from the eBook and/or eChapter(s). Editorial review has deemed that any suppressed content does not materially affect the overall learning experience. Cengage Learning reserves the right to remove additional content at any time if subsequent rights restrictions require it. 02279_FM_ptg01_hr_pi-xxxi.indd 2 9/7/12 5:30 PM To our grandchildren: Nate and Braden Barlow, Megan and Bradley Seager, and Andrew Gardner Alexander, Annie, Christian, Elyse, Foster, Megan, and Mia Slabaugh, Addison and Hadyn Hansen UUnnlleessss ootthheerrwwiissee nnootteedd aallll aarrtt oonn tthhiiss ppaaggee ©© CCeennggaaggee LLeeaarrnniinngg 22001144 Copyright 2012 Cengage Learning. All Rights Reserved. May not be copied, scanned, or duplicated, in whole or in part. Due to electronic rights, some third party content may be suppressed from the eBook and/or eChapter(s). Editorial review has deemed that any suppressed content does not materially affect the overall learning experience. Cengage Learning reserves the right to remove additional content at any time if subsequent rights restrictions require it. 02279_FM_ptg01_hr_pi-xxxi.indd 3 9/7/12 5:30 PM A b o u T T h E A u T h o r s Spencer L. Seager Spencer L. Seager is a professor of chemistry at Weber State University, where he served as chemistry department chairman from 1969 until 1993. He teaches general chemistry at the university and is also active in projects to help improve chemistry and other science education in local elementary schools. He received his B.S. degree in chemistry and Ph.D. degree in physical chemistry from the University of Utah. Other interests include making minor home repairs, reading history of science and technology, listening to classical music, and walking for exercise. Michael R. Slabaugh Michael R. Slabaugh is a senior fellow at Weber State University, where he teaches the year-long sequence of general chemistry, organic chemistry, and biochemistry. He received his B.S. degree in chemistry from Purdue University and his Ph.D. degree in organic chemistry from Iowa State University. His interest in plant alkaloids led to a year of postdoctoral study in biochemistry at Texas A&M University. His current professional interests are chemistry education and community involvement in science activities, particularly the State Science and Engineering Fair in Utah. He also enjoys the company of family, hiking in the mountains, and fishing the local streams. iv About the Authors UUnnlleessss ootthheerrwwiissee nnootteedd aallll aarrtt oonn tthhiiss ppaaggee ©© CCeennggaaggee LLeeaarrnniinngg 22001144 Copyright 2012 Cengage Learning. All Rights Reserved. May not be copied, scanned, or duplicated, in whole or in part. Due to electronic rights, some third party content may be suppressed from the eBook and/or eChapter(s). Editorial review has deemed that any suppressed content does not materially affect the overall learning experience. Cengage Learning reserves the right to remove additional content at any time if subsequent rights restrictions require it. 02279_FM_ptg01_hr_pi-xxxi.indd 4 9/7/12 5:30 PM A b o u T T h E C o v E r Dr. Melina B. Jampolis, M.D. is an internist and board-certified Physician Nutrition Specialist (one of only several hundred in the country). She specializes exclusively in nutrition for weight loss and disease prevention and treatment. A graduate of Tufts University as well as Tufts School of Medicine, she completed her residency in internal medicine at Santa Clara Valley Medical Center, a Stanford University teaching hospital. In 2005, Dr. Jampolis hosted a program on the Discovery Network’s FIT TV titled Fit TV’s Diet Doctor, and she currently serves as the diet and fitness expert for CNNHealth.com. She serves as a member of the medical advisory board of Better Homes and Gardens and VivMag.com. Her first book, The No-Time-to-Lose Diet, was released in January 2007, and the paperback version, The Busy Person’s Guide to Permanent Weight Loss, was released in May 2008. Her latest book, The Calendar Diet, was released in March 2012. Dr. Jampolis lectures throughout the country on nutrition for weight loss and optimal health. She has been interviewed on nutrition and weight loss–related topics by USA Today, USA Weekend, New York Post, The Washington Post, Family Circle, Better Homes and Gardens, Glamour.com, Ladies’ Home Journal, First for Women, Women’s World, Alternative Medicine, Women’s Health, SanFrancisco Magazine, Clean Eating, Baby Talk, and more. She has appeared numerous times on Live with Regis & Kelly, CNN, FOX News Channel, FOX Business Network, as well as on The Dr. Oz Show, Dr. Drew’s Lifechangers, and local television and radio stations, including ABC, NBC, FOX, KGO radio, and KRON-4 news. Dr. Jampolis lives in Los Angeles with her husband and two-year-old son. She maintains a small private practice in San Francisco and Los Angeles. UUnnlleessss ootthheerrwwiissee nnootteedd aallll aarrtt oonn tthhiiss ppaaggee ©© CCeennggaaggee LLeeaarrnniinngg 22001144 About the Cover   v Copyright 2012 Cengage Learning. All Rights Reserved. May not be copied, scanned, or duplicated, in whole or in part. Due to electronic rights, some third party content may be suppressed from the eBook and/or eChapter(s). Editorial review has deemed that any suppressed content does not materially affect the overall learning experience. Cengage Learning reserves the right to remove additional content at any time if subsequent rights restrictions require it. 02279_FM_ptg01_hr_pi-xxxi.indd 5 9/7/12 5:30 PM A b o u T T h E C o v E r DR. MELINA B. JAMPOLIS, M.D. Ask an Expert Q: Do foods, medications, and supplements interact? Michael Roud Photography Ammalt:ea endMryeic odams tmtiao yepn tnesa.oo bTtpo hlbleeies sma ear .wei n atarewer aaocrfet it othnhesa itgn emtenereadrcaictlilaoyt nrioe osnfus l ctce farrntoa miinn tefeiotrhoaedcrts iwamniptdha isoruenpdep alaebnmsooetrhnpettsiro, wnb iuothtr © Iron, present in food and supplements, has numerous clinically relevant interac- Dr. Melina B. Jampolis, M.D. tions. Absorption of heme iron from meat protein is very efficient and differs from the is a Los Angeles, California, absorption of non-heme iron such as that found in plant foods and supplements. Non- Physician Nutrition Specialist—a specialty heme iron must be digested and converted to a soluble and ionized form in order to practiced by only a few be absorbed in the intestine. This process is enhanced by gastric acid which improves hundred physicians in the the solubility of iron and reduces it to ferrous iron (2 + oxidation state) for better ab- United States. She focuses exclusively on nutrition for sorption. Acid reducing medications such as proton pump inhibitors and antacids re- weight loss and disease duce the absorption of non-heme iron by decreasing the acidity in the stomach and prevention and treatment. upper duodenum. Tannins found in tea and phytates found in legumes and wheat bran may also impair iron absorption by chelating iron, preventing its absorption. Ascorbic acid (vitamin C) enhances absorption by reducing ferric to ferrous iron and chelating ferrous iron, improving its absorption at the higher pH of the regions of the small intestine located farthest from the stomach. Calcium supplements and dairy foods also impair iron absorption. Ferrous iron can also interact with several types of medications including the antibiotics ciprofloxacin and tetracycline, and thyroid medication. It impairs their absorption and thereby potentially reduces their effectiveness as medications. Calcium, also found in both dairy foods and some supplements, has several food and drug interactions. Like iron, calcium is only absorbed in ionic form. It too requires an acidic environment for optimal absorption, particularly when it is in the calcium carbonate form. This form is best taken with meals. Unlike iron, more calcium is absorbed in the parts of the small intestine located farthest from the acidic stomach. As a result, acid blocking medications are not as detrimental to absorption as they are for iron. But calcium citrate, which is more soluble at a neutral pH, may still be the preferable form for those with compro- mised levels of stomach acid. Phytates and oxalic acid, found in spinach, rhubarb, collard greens, sweet potatoes and beans bind calcium, creating insoluble complexes that cannot be absorbed. Calcium can also decrease the absorption of several medications including quinolone antibiotics, tetracycline, and thyroid replacement medication. Unlike iron and calcium which interact with medications by preventing their absorption, grapefruit interacts with numer- ous medications through its effect on drug metabolism. A flavonoid compound in grapefruit inhibits an enzyme, cytochrome P450 3A4, that is important for the degradation of numerous drugs. Since less of the drug is broken down when consumed with grapefruit or grapefruit juice, more of the drug is bioavailable, which can potentially lead to toxic levels in some cases. In addition to several of the cholesterol reducing statin medications, other drugs affected this way include several blood pres- sure lowering medications, the anti-retroviral medication saquinavir, and the immunosuppressive medication cyclosporine. St. John’s wort, a popular herbal supplement often used for the treatment of mild depression, may enhance rather than suppress the cytochrome P450 34A system in a clinically relevant manner, potentially reducing the effectiveness of several HIV medications, immunosuppressive medications, and even cancer treatment drugs. There are numerous other food, drug and supplement interactions. While not all of them may be clinically relevant, their presence underscore the importance of discussing both supplementation and diet with appropriate health care provider. This is especially true if you are taking prescription medication or supplements to treat a deficiency or medical condition. vi About the Cover Unless otherwise noted all art on this page © Cengage Learning 2014 Copyright 2012 Cengage Learning. All Rights Reserved. May not be copied, scanned, or duplicated, in whole or in part. Due to electronic rights, some third party content may be suppressed from the eBook and/or eChapter(s). Editorial review has deemed that any suppressed content does not materially affect the overall learning experience. Cengage Learning reserves the right to remove additional content at any time if subsequent rights restrictions require it. 02279_FM_ptg01_hr_pi-xxxi.indd 6 9/7/12 5:30 PM b r i E f C o n T E n T s Chapter 1 Chapter 13 Matter, Measurements, and Alcohols, Phenols, and Ethers 432 Calculations 2 Chapter 14 Chapter 2 Aldehydes and Ketones 466 Atoms and Molecules 46 Chapter 15 Chapter 3 Carboxylic Acids and Esters 496 Electronic Structure and the Chapter 16 Periodic Law 72 Amines and Amides 526 Chapter 4 Chapter 17 Forces Between Particles 102 Carbohydrates 558 Chapter 5 Chapter 18 Chemical Reactions 146 Lipids 592 Chapter 6 Chapter 19 The States of Matter 176 Proteins 622 Chapter 7 Chapter 20 Solutions and Colloids 214 Enzymes 654 Chapter 8 Chapter 21 Reaction Rates and Equilibrium 254 Nucleic Acids and Protein Synthesis 680 Chapter 9 Chapter 22 Acids, Bases, and Salts 282 Nutrition and Energy for Life 716 Chapter 10 Chapter 23 Radioactivity and Nuclear Processes 328 Carbohydrate Metabolism 746 Chapter 11 Chapter 24 Organic Compounds: Alkanes 360 Lipid and Amino Acid Metabolism 774 Chapter 12 Chapter 25 Unsaturated Hydrocarbons 398 Body Fluids 802 Unless otherwise noted all art on this page © Cengage Learning 2014 Brief Contents   vii Copyright 2012 Cengage Learning. All Rights Reserved. May not be copied, scanned, or duplicated, in whole or in part. Due to electronic rights, some third party content may be suppressed from the eBook and/or eChapter(s). Editorial review has deemed that any suppressed content does not materially affect the overall learning experience. Cengage Learning reserves the right to remove additional content at any time if subsequent rights restrictions require it. 02279_FM_ptg01_hr_pi-xxxi.indd 7 9/7/12 5:30 PM Copyright 2012 Cengage Learning. All Rights Reserved. May not be copied, scanned, or duplicated, in whole or in part. Due to electronic rights, some third party content may be suppressed from the eBook and/or eChapter(s). Editorial review has deemed that any suppressed content does not materially affect the overall learning experience. Cengage Learning reserves the right to remove additional content at any time if subsequent rights restrictions require it. 02279_FM_ptg01_hr_pi-xxxi.indd 8 9/7/12 5:30 PM