Organic and Biochemistry for Today

552 Pages·2013·102.057 MB·English

by  Spencer L. Seager, Michael R. Slabaugh

1 2 3 4 5 6 7 6 7
m
NobleGases(18)VIIIA 2HeHelium4.003 10NeNeon20.18 18ArArgon39.95 36KrKrypton83.80 54XeXenon131.3 86RnRadon(222) 118——(294) 71LuLutetium175.0 103LrLawrenciu(262)
(17)VIIA 9FFluorine19.00 17ClChlorine35.45 35BrBromine79.90 53IIodine126.9 85AtAstatine(210) 117——(294) 70YbYtterbium173.0 102NoNobelium(259)
m m
(16)VIA 8OOxygen16.00 16SSulfur32.06 34SeSelenium78.96 52TeTellurium127.6 84PoPolonium(209) 116LvLivermoriu(293) 69TmThulium168.9 101MdMendeleviu(258)
(15)VA 7NNitrogen14.01 15Phosphorus30.97 33AsArsenic74.92 51SbAntimony121.8 83BiBismuth209.0 115——(288) 68ErErbium167.3 100FmFermium(257)
P
(14)IVA 6CCarbon12.01 14SiSilicon28.09 32GeGermanium72.63 50SnTin118.7 82PbLead207.2 114FlFlerovium(289) 67HoHolmium164.9 99EsEinsteinium(252)
(13)IIIA 5BBoron10.81 13AlAluminum26.98 31GaGallium69.72 49InIndium114.8 81TlThallium204.4 113——(284) 66DyDysprosium162.5 98CfCalifornium(251)
m
(12)IIB 30ZnZinc65.38 48CdCadmium112.4 80HgMercury200.6 112CnCoperniciu(285) 65TbTerbium158.9 97BkBerkelium(247)
m
(11)IB 29CuCopper63.55 47AgSilver107.9 79AuGold197.0 111Rgoentgeniu(280) 64GdGadolium157.3 96CmCurium(247)
R
m
gases (10) 28NiNickel58.69 46PdPalladium106.4 78PtPlatinum195.1 110DsDarmstadtiu(281) 63EuEuropium152.0 95AmAmericium(243)
NTS ds als, noble (9)VIIIB 27CoCobalt58.93 45RhRhodium102.9 77IrIridium192.2 109MtMeitnerium(276) 62SmSamarium150.4 94PuPlutonium(244)
E ELEME Metals Metalloi Nonmet (8) 26FeIron55.85 44RuRuthenium101.1 76OsOsmium190.2 108HsHassium(277) 61PmPromethium(145) 93NpNeptunium(237)
TABLE OF TH Atomic numberSymbolNameAtomic weight(rounded to foursignificant figures) (6)(7)VIBVIIB 2425CrMnChromiumManganese52.0054.94 4243MoTcMolybdenumTechnetium95.96(98) 7475WReTungstenRhenium183.8186.2 106107SgBhSeaborgiumBohrium(271)(270) 5960PrNdPraseodymiumNeodymium140.9144.2 9192PaUUraniumProtactinium238.0231.0
IODIC Y 79AuGold197.0 (5)VB 23VVanadium50.94 41NbNiobium92.91 73TaTantalum180.9 105DbDubnium(268) 58CeCerium140.1 90ThThorium232.0
PER KE upgnation (4)IVB 22TiTitanium47.87 40ZrZirconium91.22 72HfHafnium178.5 104RfRutherfordium(265) 6 7
(1)IA 1H(2)HydrogenGroIIA1.008desi43LiBeLithiumBeryllium6.949.012 1112NaMg(3)SodiumMagnesiumIIIB22.9924.31 192021ScKCaPotassiumCalciumScandium39.1040.0844.96 373938RbSrYRubidiumStrontiumYttrium85.4787.6288.91 555657CsLaBaCesiumLanthanumBarium132.9138.9137.3 888987FrRaAcFranciumRadiumActinium(223)(226)(227) Mass numbers in parentheses are the most stable radioactive isotope.
1 2 3 4 5 6 7
er,m er,
umbyste umbem
Group nIUPAC s Group nU.S. syst Periodnumber
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E i g h T h E d i T i O n
Organic and
Biochemistry for Today
Spencer L. Seager
Weber State University
Michael R. Slabaugh
Weber State University
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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
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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
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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.
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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
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B r i E f C O n T E n T s
Chapter 1 Chapter 9
Organic Compounds: Alkanes 2 Proteins 264
Chapter 2 Chapter 10
Unsaturated Hydrocarbons 40 Enzymes 296
Chapter 3 Chapter 11
Alcohols, Phenols, and Ethers 74 Nucleic Acids and Protein Synthesis 322
Chapter 4 Chapter 12
Aldehydes and Ketones 108 Nutrition and Energy for Life 358
Chapter 5 Chapter 13
Carboxylic Acids and Esters 138 Carbohydrate Metabolism 388
Chapter 6 Chapter 14
Amines and Amides 168 Lipid and Amino Acid Metabolism 416
Chapter 7 Chapter 15
Carbohydrates 200 Body Fluids 444
Chapter 8
Lipids 234
Unless otherwise noted all art on this page © Cengage Learning 2014 Brief Contents   vii
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