Introduction to Organic and Biochemistry

673 Pages·2008·20.42 MB·English

by  Frederick A. Bettelheim

INTRODUCTION TO
Organic and
Biochemistry
SEVENTH EDITION
Frederick A. Bettelheim
William H. Brown
Beloit College
Mary K. Campbell
Mount Holyoke College
Shawn O. Farrell
Olympic Training Center
Australia • Brazil • Japan • Korea • Mexico • Singapore • Spain • United Kingdom • United States
Hydrogen 8A
Period
1 (18)
number 1
H Uranium Helium
Group number, 1.0079 METALS 92 Atomic number 2
U.S. system 1A 2A 3A 4A 5A 6A 7A He
Group number, (1) (2) METALLOIDS U Symbol (13) (14) (15) (16) (17) 4.0026
IUPAC system
Lithium Beryllium Boron Carbon Nitrogen Oxygen Fluorine Neon
NONMETALS 238.0289 Atomic weight
3 4 5 6 7 8 9 10
2
Li Be B C N O F Ne
6.941 9.0122 10.811 12.011 14.0067 15.9994 18.9984 20.1797
Sodium Magnesium Aluminum Silicon Phosphorus Sulfur Chlorine Argon
11 12 13 14 15 16 17 18
3 Na Mg 3B 4B 5B 6B 7B 8B 1B 2B Al Si P S Cl Ar
22.9898 24.3050 (3) (4) (5) (6) (7) (8) (9) (10) (11) (12) 26.9815 28.0855 30.9738 32.066 35.4527 39.948
Potassium Calcium Scandium Titanium Vanadium Chromium Manganese Iron Cobalt Nickel Copper Zinc Gallium Germanium Arsenic Selenium Bromine Krypton
19 20 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36
4
K Ca Sc Ti V Cr Mn Fe Co Ni Cu Zn Ga Ge As Se Br Kr
39.0983 40.078 44.9559 47.867 50.9415 51.9961 54.9380 55.845 58.9332 58.6934 63.546 65.38 69.723 72.61 74.9216 78.96 79.904 83.80
Rubidium Strontium Yttrium Zirconium Niobium Molybdenum Technetium Ruthenium Rhodium Palladium Silver Cadmium Indium Tin Antimony Tellurium Iodine Xenon
37 38 39 40 41 42 43 44 45 46 47 48 49 50 51 52 53 54
5
Rb Sr Y Zr Nb Mo Tc Ru Rh Pd Ag Cd In Sn Sb Te I Xe
85.4678 87.62 88.9059 91.224 92.9064 95.96 (97.907) 101.07 102.9055 106.42 107.8682 112.411 114.818 118.710 121.760 127.60 126.9045 131.29
Cesium Barium Lanthanum Hafnium Tantalum Tungsten Rhenium Osmium Iridium Platinum Gold Mercury Thallium Lead Bismuth Polonium Astatine Radon
55 56 57 72 73 74 75 76 77 78 79 80 81 82 83 84 85 86
6 Cs Ba La Hf Ta W Re Os Ir Pt Au Hg Tl Pb Bi Po At Rn
132.9054 137.327 138.9055 178.49 180.9488 183.84 186.207 190.2 192.22 195.084 196.9666 200.59 204.3833 207.2 208.9804 (208.98) (209.99) (222.02)
Francium Radium Actinium Rutherfordium Dubnium Seaborgium Bohrium Hassium Meitnerium Darmstadtium Roentgenium — — — — — —
87 88 89 104 105 106 107 108 109 110 111 112 113 114 115 116 118
7 Fr Ra Ac Rf Db Sg Bh Hs Mt Ds Rg — — — — — —
Discovered Discovered Discovered Discovered Discovered Discovered
(223.02) (226.0254) (227.0278) (261.11) (262.11) (263.12) (262.12) (265) (266) (271) (272) 1996 2004 1999 2004 1999 2006
Cerium Praseodymium Neodymium Promethium Samarium Europium Gadolinium Terbium Dysprosium Holmium Erbium Thulium Ytterbium Lutetium
58 59 60 61 62 63 64 65 66 67 68 69 70 71
Lanthanides
Note: Atomic masses are Ce Pr Nd Pm Sm Eu Gd Tb Dy Ho Er Tm Yb Lu
2007 IUPAC values (up to 140.115 140.9076 144.24 (144.91) 150.36 151.965 157.25 158.9253 162.50 164.9303 167.26 168.9342 173.54 174.9668
four decimal places).
Thorium Protactinium Uranium Neptunium Plutonium Americium Curium Berkelium Californium Einsteinium Fermium Mendelevium Nobelium Lawrencium
Numbers in parentheses are
90 91 92 93 94 95 96 97 98 99 100 101 102 103
atomic masses or mass Actinides
Th Pa U Np Pu Am Cm Bk Cf Es Fm Md No Lr
numbers of the most stable
isotope of an element. 232.0381 231.0388 238.0289 (237.0482) (244.664) (243.061) (247.07) (247.07) (251.08) (252.08) (257.10) (258.10) (259.10) (262.11)
STANDARD ATOMIC WEIGHTS OF THE ELEMENTS 2007 Based on relative atomic mass of 12C 5 12, where 12C is a neutral
atom in its nuclear and electronic ground state.†
Atomic Atomic Atomic Atomic
Name Symbol Number Weight Name Symbol Number Weight
Actinium* Ac 89 (227) Neodymium Nd 60 144.22(3)
Aluminum Al 13 26.9815386(8) Neon Ne 10 20.1797(6)
Americium* Am 95 (243) Neptunium* Np 93 (237)
Antimony Sb 51 121.760(1) Nickel Ni 28 58.6934(4)
Argon Ar 18 39.948(1) Niobium Nb 41 92.90638(2)
Arsenic As 33 74.92160(2) Nitrogen N 7 14.0067(2)
Astatine* At 85 (210) Nobelium* No 102 (259)
Barium Ba 56 137.327(7) Osmium Os 76 190.23(3)
Berkelium* Bk 97 (247) Oxygen O 8 15.9994(3)
Beryllium Be 4 9.012182(3) Palladium Pd 46 106.42(1)
Bismuth Bi 83 208.98040(1) Phosphorus P 15 30.973762(2)
Bohrium Bh 107 (264) Platinum Pt 78 195.084(9)
Boron B 5 10.811(7) Plutonium* Pu 94 (244)
Bromine Br 35 79.904(1) Polonium* Po 84 (209)
Cadmium Cd 48 112.411(8) Potassium K 19 39.0983(1)
Cesium Cs 55 132.9054519(2) Praseodymium Pr 59 140.90765(2)
Calcium Ca 20 40.078(4) Promethium* Pm 61 (145)
Californium* Cf 98 (251) Protactinium* Pa 91 231.03588(2)
Carbon C 6 12.0107(8) Radium* Ra 88 (226)
Cerium Ce 58 140.116(1) Radon* Rn 86 (222)
Chlorine Cl 17 35.453(2) Rhenium Re 75 186.207(1)
Chromium Cr 24 51.9961(6) Rhodium Rh 45 102.90550(2)
Cobalt Co 27 58.933195(5) Roentgenium Rg 111 (272)
Copper Cu 29 63.546(3) Rubidium Rb 37 85.4678(3)
Curium* Cm 96 (247) Ruthenium Ru 44 101.07(2)
Darmstadtium Ds 110 (271) Rutherfordium Rf 104 (261)
Dubnium Db 105 (262) Samarium Sm 62 150.36(2)
Dysprosium Dy 66 162.500(1) Scandium Sc 21 44.955912(6)
Einsteinium* Es 99 (252) Seaborgium Sg 106 (266)
Erbium Er 68 167.259(3) Selenium Se 34 78.96(3)
Europium Eu 63 151.964(1) Silicon Si 14 28.0855(3)
Fermium* Fm 100 (257) Silver Ag 47 107.8682(2)
Fluorine F 9 18.9984032(5) Sodium Na 11 22.9896928(2)
Francium* Fr 87 (223) Strontium Sr 38 87.62(1)
Gadolinium Gd 64 157.25(3) Sulfur S 16 32.065(5)
Gallium Ga 31 69.723(1) Tantalum Ta 73 180.9488(2)
Germanium Ge 32 72.64(1) Technetium* Tc 43 (98)
Gold Au 79 196.966569(4) Tellurium Te 52 127.60(3)
Hafnium Hf 72 178.49(2) Terbium Tb 65 158.92535(2)
Hassium Hs 108 (277) Thallium Tl 81 204.3833(2)
Helium He 2 4.002602(2) Thorium* Th 90 232.03806(2)
Holmium Ho 67 164.93032(2) Thulium Tm 69 168.93421(2)
Hydrogen H 1 1.00794(7) Tin Sn 50 118.710(7)
Indium In 49 114.818(3) Titanium Ti 22 47.867(1)
Iodine I 53 126.90447(3) Tungsten W 74 183.84(1)
Iridium Ir 77 192.217(3) Ununbium Uub 112 (285)
Iron Fe 26 55.845(2) Ununhexium Uuh 116 (292)
Krypton Kr 36 83.798(2) Ununoctium Uuo 118 (294)
Lanthanum La 57 138.90547(7) Ununpentium Uup 115 (228)
Lawrencium* Lr 103 (262) Ununquadium Uuq 114 (289)
Lead Pb 82 207.2(1) Ununtrium Uut 113 (284)
Lithium Li 3 6.941(2) Uranium* U 92 238.02891(3)
Lutetium Lu 71 174.9668(1) Vanadium V 23 50.9415(1)
Magnesium Mg 12 24.3050(6) Xenon Xe 54 131.293(6)
Manganese Mn 25 54.938045(5) Ytterbium Yb 70 173.54(5)
Meitnerium Mt 109 (268) Yttrium Y 39 88.90585(2)
Mendelevium* Md 101 (258) Zinc Zn 30 65.38(2)
Mercury Hg 80 200.59(2) Zirconium Zr 40 91.224(2)
Molybdenum Mo 42 95.96(2)
†The atomic weights of many elements can vary depending on the origin *Elements with no stable nuclide; the value given in parentheses is the
and treatment of the sample. This is particularly true for Li; commercially atomic mass number of the isotope of longest known half-life. However,
available lithium-containing materials have Li atomic weights in the three such elements (Th, Pa, and U) have a characteristic terrestial isoto-
range of 6.939 and 6.996. The uncertainties in atomic weight values are pic composition, and the atomic weight is tabulated for these. http://www
given in parentheses following the last significant figure to which they are . chem.qmw.ac.uk/iupac/AtWt/
attributed.
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Introduction to Organic and Biochemistry, © 2010 Brooks/Cole, Cengage Learning
Seventh Edition
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To my lovely wife, Courtney — Between textbook revisions, a
full-time job, and school, I have been little more than a ghost
around the house, hiding in my study writing. Courtney held
the family together, taking care of our children and our
home while maintaining her own writing schedule. None of this
would have been possible without her love, support, and
tireless effort. —SF
To my grandchildren for the love and joy they bring
to my life: Emily, Sophia, and Oscar; Amanda and Laura;
Rachel; Gabrielle and Max. —WB
To Andrew, Christian, and Sasha — Thank you for the rewards
of being your mom. And to Bill, Mary, and Shawn. — It is
always a pleasure to work with you. —SK
Contents in Brief
Organic Chemistry
Chapter 1 Organic Chemistry 1
Chapter 2 Alkanes 17
Chapter 3 Alkenes and Alkynes 46
Chapter 4 Benzene and Its Derivatives 76
Chapter 5 Alcohols, Ethers, and Thiols 91
Chapter 6 Chirality: The Handedness of
Molecules 114
Chapter 7 Acids and Bases 135
Chapter 8 Amines 171
Chapter 9 Aldehydes and Ketones 187
Chapter 10 Carboxylic Acids 205
Chapter 11 Carboxylic Anhydrides, Esters, and Amides 228
Biochemistry
Chapter 12 Carbohydrates 247
Chapter 13 Lipids 276
Chapter 14 Proteins 308
Chapter 15 Enzymes 344
Chapter 16 Chemical Communicators: Neurotransmitters and Hormones 369
Chapter 17 Nucleotides, Nucleic Acids, and Heredity 395
Chapter 18 Gene Expression and Protein Synthesis 425
Chapter 19 Bioenergetics: How the Body Converts Food to Energy 456
Chapter 20 Specifi c Catabolic Pathways: Carbohydrate,
Lipid, and Protein Metabolism 477
iv
Contents in Brief ■ v
Chapter 21 Biosynthetic Pathways 502
Chapter 22 Nutrition 517
Chapter 23 Immunochemistry 539
Body Fluids
(This chapter can be found on this book’s companion website, which is accessible from
www.cengage.com/chemistry/bettelheim)
Contents
Chapter 1 Organic Chemistry 1 3.7 What Are the Important Polymerization Reactions
of Ethylene and Substituted Ethylenes? 64
1.1 What Is Organic Chemistry? 1
Summary of Key Questions 69
1.2 Where Do We Obtain Organic Compounds? 3
Summary of Key Reactions 69
1.3 How Do We Write Structural Formulas of Organic
Problems 70
Compounds? 5
Chemical Connections
1.4 What Is a Functional Group? 7
Summary of Key Questions 13 3A Ethylene: A Plant Growth Regulator 47
Problems 13 3B The Case of the Iowa and New York Strains of the
European Corn Borer 52
Chemical Connections
3C Cis-Trans Isomerism in Vision 55
1A Taxol: A Story of Search and Discovery 4 3D Recycling Plastics 68
Chapter 2 Alkanes 17
Chapter 4 Benzene and
2.1 How Do We Write Structural Formulas of Alkanes? 17 Its Derivatives 76
2.2 What Are Constitutional Isomers? 20
2.3 How Do We Name Alkanes? 22 4.1 What Is the Structure of
2.4 Where Do We Obtain Alkanes? 26 Benzene? 76
2.5 What Are Cycloalkanes? 26 4.2 How Do We Name Aromatic
2.6 What Are the Shapes of Alkanes and Compounds? 78
Cycloalkanes? 28 4.3 What Are the Characteristic
2.7 What Is Cis-Trans Isomerism in Cycloalkanes? 31 Reactions of Benzene
2.8 What Are the Physical Properties of Alkanes? 34 and Its Derivatives? 81
2.9 What Are the Characteristic Reactions of 4.4 What Are Phenols? 83
Alkanes 36 S ummary of Key
2.10 What Are Some Important Haloalkanes? 38 Questions 87
Summary of Key Questions 40 Summary of Key
Summary of Key Reactions 40 Reactions 88
Problems 41 Problems 88
Chemical Connections Chemical Connections
2A The Poisonous Puffer Fish 31 4A Carcinogenic Polynuclear Aromatics and Smoking 81
2B Octane Rating: What Those Numbers at the 4B Iodide Ion and Goiter 82
Pump Mean 37 4C The Nitro Group in Explosives 83
2C The Environmental Impact of Freons 39 4D FD & C No. 6 (a.k.a. Sunset Yellow) 85
4E Capsaicin, for Those Who Like It Hot 86
Chapter 3 Alkenes and Alkynes 46
Chapter 5 Alcohols, Ethers,
3.1 What Are Alkenes and Alkynes? 46
and Thiols 91
3.2 What Are the Structures of Alkenes and Alkynes? 48
3.3 How Do We Name Alkenes and Alkynes? 49 5.1 What Are the Structures, Names, and Physical
3.4 What Are the Physical Properties of Alkenes Properties of Alcohols? 92
and Alkynes? 55 5.2 What Are the Characteristic Reactions of
3.5 What Are Terpenes? 56 Alcohols? 96
3.6 What Are the Characteristic Reactions of 5.3 What Are the Structures, Names, and Properties
Alkenes? 57 of Ethers? 102
vi
Contents ■ vii
5.4 What Are the Structures, Names, and Properties Chemical Connections
of Thiols? 105 7A Some Important Acids and Bases 138
5.5 What Are the Most Commercially Important 7B Drugstore Antacids 148
Alcohols? 107 7C Respiratory and Metabolic Acidosis 163
Summary of Key Questions 108 7D Alkalosis and the Sprinter’s Trick 164
Summary of Key Reactions 109
Chapter 8 Amines 171
Problems 109
5A Nitroglycerin: An Explosive and a Drug 95 8.1 What Are Amines? 171
5B Breath-Alcohol Screening 101 8.2 How Do We Name Amines? 174
5C Ethylene Oxide: A Chemical Sterilant 103 8.3 What Are the Physical Properties of Amines? 176
5D Ethers and Anesthesia 104 8.4 How Do We Describe the Basicity of Amines? 177
8.5 What are the Characteristic Reactions of Amines? 179
Chapter 6 Chirality: The
Summary of Key Questions 182
Handedness of Molecules 114
Summary of Key Reactions 183
Problems 183
6.1 What Is Enantiomerism? 114
Chemical Connections
How To... Draw Enantiomers 118
6.2 How Do We Specify the Confi guration of a 8A Amphetamines (Pep Pills) 172
Stereocenter? 121 8B Alkaloids 173
6.3 How Many Stereoisomers Are Possible for Molecules 8C Tranquilizers 176
with Two or More Stereocenters? 124 8D The Solubility of Drugs in
Body Fluids 180
6.4 What Is Optical Activity, and How Is Chirality
8E Epinephrine: A
Detected in the Laboratory? 128
Prototype for the
6.5 What Is the Signifi cance of Chirality in the
Development of New
Biological World? 130
Bronchodilators 181
Summary of Key Questions 131
Problems 131
Chapter 9 Aldehydes and Ketones 187
Chemical Connections
9.1 What Are Aldehydes and Ketones 187
6A Chiral Drugs 128
9.2 How Do We Name Aldehydes and Ketones? 188
9.3 What Are the Physical Properties of Aldehydes and
Chapter 7 Acids and Bases 135
Ketones? 191
7.1 What Are Acids and Bases? 135 9.4 What Are the Characteristic Reactions of Aldehydes
7.2 How Do We Defi ne the Strength of Acids and and Ketones? 192
Bases? 137 9.5 What Is Keto-Enol Tautomerism? 198
7.3 What Are Conjugate Acid-Base Summary of Key Questions 199
Pairs? 139 Summary of Key Reactions 199
How To... Name Common Acids 141 Problems 200
7.4 How Can We Tell the Position of Equilibrium in an Chemical Connections
Acid-Base Reaction? 142
9A Some Naturally Occurring Aldehydes and Ketones 191
7.5 How Do We Use Acid Ionization
Constants? 144
Chapter 10 Carboxylic Acids 205
7.6 What Are the Properties of Acids and
Bases? 145 10.1 What Are Carboxylic Acids? 205
7.7 What Are the Acidic and Basic Properties of 10.2 How Do We Name Carboxylic Acids? 205
Pure Water? 148 10.3 What Are the Physical Properties of Carboxylic
How To... Use Logs and Antilogs 150 Acids? 208
10.4 What Are Soaps and Detergents? 209
7.8 What Are pH and pOH? 151
10.5 What Are the Characteristic Reactions of Carboxylic
7.9 How Do We Use Titration to Calculate
Acids? 215
Concentration? 154
7.10 What Are Buffers? 156 Summary of Key Questions 222
7.11 How Do We Calculate the pH of a Buffer? 160 Summary of Key Reactions 222
7.12 What Are TRIS, HEPES, and These Buffers with the Problems 223
Strange Names? 162 Chemical Connections
Summary of Key Questions 165 10A Trans Fatty Acid: What Are They and How Do You
Problems 166 Avoid Them? 211