The facts on file dictionary of organic chemistry

The Facts On File DICTIONARY of ORGANIC CHEMISTRY The Facts On File DICTIONARY of ORGANIC CHEMISTRY Edited by John Daintith ® The Facts On File Dictionary of Organic Chemistry Copyright © 2004 by Market House Books Ltd All rights reserved No part of this book may be reproduced or utilized in any form or by any means, electronic or mechanical, including photocopying, recording, or by any information storage or retrieval systems, without permission in writing from the publisher For information contact: Facts On File, Inc 132 West 31st Street New York NY 10001 Library of Congress Cataloging-in-Publication Data The Facts on File dictionary of organic chemistry / edited by John Daintith p cm Includes bibliographical references ISBN 0-8160-4928-9 (alk paper) Chemistry—Dictionaries I Title: Dictionary of organic chemistry II Daintith, John XXXXXXXXX XXXXXXXXX XXXXXXXXXX Facts On File books are available at special discounts when purchased in bulk quantities for businesses, associations, institutions, or sales promotions Please call our Special Sales Department in New York at (212) 967-8800 or (800) 322-8755 You can find Facts On File on the World Wide Web at http://www.factsonfile.com Compiled and typeset by Market House Books Ltd, Aylesbury, UK Printed in the United States of America MP 10 This book is printed on acid-free paper CONTENTS Preface vii Entries A to Z Appendixes I Carboxylic Acids 233 II Amino Acids 235 III Sugars 238 IV Nitrogenous Bases and V Nucleosides 239 The Chemical Elements 241 VI The Periodic Table 243 VII The Greek Alphabet 244 VIII Fundamental Constants 245 IX Webpages 246 Bibliography 247 PREFACE This dictionary is one of a series covering the terminology and concepts used in important branches of science The Facts on File Dictionary of Organic Chemistry has been designed as an additional source of information for students taking Advanced Placement (AP) Science courses in high schools It will also be helpful to older students taking introductory college courses This volume covers organic chemistry and includes basic concepts, classes of compound, reaction mechanisms, and important named organic compounds In addition, we have included a number of compounds that are important in biochemistry, as well as information on certain key biochemical pathways The definitions are intended to be clear and informative and, where possible, we have illustrations of chemical structures The book also has a selection of short biographical entries for people who have made important contributions to the field There are a number of appendixes, including structural information on carboxylic acids, amino acids, sugars, and nitrogenous bases and nucleosides There is also a list of all the chemical elements and a periodic table The appendixes also include a short list of useful webpages and a bibliography The book will be a helpful additional source of information for anyone studying the AP Chemistry course, especially the section on Descriptive Chemistry It will also be useful to students of AP Biology ACKNOWLEDGMENTS Contributors John O E Clark B.Sc Richard Rennie B.Sc., Ph.D vii A ABA See abscisic acid temperature intervals were called degrees absolute (°A) or degrees Kelvin (°K), and were equal to the Celsius degree It can be shown that the absolute temperature scale is identical to the currently used thermodynamic temperature scale (on which the unit is the KELVIN) abscisic acid (ABA) A PLANT HORMONE once thought to be responsible for the shedding (abscission) of flowers and fruit and for the onset of dormancy in buds (hence its early name, dormin) The compound is associated with the closing of pores (stoma) in the leaves of plants deprived of water absolute zero The zero value of thermodynamic temperature; kelvin or –273.15°C See absolute temperature absolute alcohol Pure alcohol (ethanol) absorption A process in which a gas is taken up by a liquid or solid, or in which a liquid is taken up by a solid In absorption, the substance absorbed goes into the bulk of the material Solids that absorb gases or liquids often have a porous structure The absorption of gases in solids is sometimes called sorption There is a distinction between absorption (in which one substance is assimilated into the bulk of another) and ADSORPTION (which involves attachment to the surface) Sometimes it is not obvious which process is occurring For example, a porous solid, such as activated CHARCOAL may be said to absorb a large volume of gas, but the process may actually be adsorption on the high surface area of internal pores in the material The process in which electromagnetic radiation, particles, or sound waves lose energy in passing through a medium Absorption involves conversion of one form of energy into another absolute configuration A particular molecular configuration of a CHIRAL molecule, as denoted by comparison with a reference molecule or by some sequence rule There are two systems for expressing absolute configuration in common use: the D–L convention and the R–S convention See optical activity absolute temperature Symbol: T A temperature defined by the relationship: T = θ + 273.15 where θ is the Celsius temperature The absolute scale of temperature was a fundamental scale based on Charles’ law, which applies to an ideal gas: V = V0(1 + αθ) where V is the volume at temperature θ, V0 the volume at 0, and α the thermal expansivity of the gas At low pressures (where real gases show ideal behavior) α has the value 1/273.15 Therefore, at θ = –273.15 the volume of the gas theoretically becomes zero In practice substances become solids at these temperatures; however, the extrapolation can be used for a scale of temperature on which –273.15°C corresponds to 0° (absolute zero) The scale is also known as the ideal-gas scale; on it absorption spectrum See spectrum accelerator A substance that increases the rate of a chemical reaction In this sense the term is synonymous with CATALYST It is common to refer to catalysts as ‘acceler1 Appendix I Examples of unsaturated dicarboxylic acids are: cis-butenedioic trans-butenedioic maleic fumaric HOOCCH=CHCOOH HOOCCH=CHCOOH Certain hydroxy acids occur naturally: hydroxyethanoic 2-hydroxypropanoic hydroxybutanedioic 2-hydroxy-propane-1,2,3-tricarboxylic glycolic lactic malic citric CH2(OH)COOH CH3CH(OH)COOH CH(OH)CH2(COOH)2 (CH2)2C(OH)(COOH)3 Naturally occurring amino carboxylic acids are shown in Appendix II 234 Appendix II Amino Acids NH H3C COOH H C H2N N H NH2 alanine H2 C C H2 COOH H C NH2 H2 C O OH NH2 asparagine H C HS COOH C H2 H C COOH NH2 H2 C H C NH2 NH2 glutamic acid cysteine O H2N C H2 glutamine COOH aspartine HOOC H2 C H C NH2 arginine H2 C O H2 C H2 C H2C H C COOH NH2 NH2 glycine 235 COOH COOH Appendix II Amino Acids H2 C N O CH3 COOH H C H3C C H2 HC N H CH NH2 H C isoleucine H2 C CH3 H2N H C C H2 COOH H2 C C H2 H2 C NH2 H C COOH NH2 leucine H3C COOH H C NH2 histidine H3C C H O lysine S C H2 H2 C HC H C COOH HC CH C H NH2 methionine H2 C H2C phenylalanine H C H2 C COOH HO C H2 H2 C H C H C NH NH2 proline serine 236 COOH H C NH2 COOH Appendix II Amino Acids H C OH H3C C H C H CH NH2 H C NH2 N H threonine tryptophan H2 C H C HC CH HO H2 C HC COOH H C H C C H CH3 H C COOH H3C C H NH2 H C NH2 tyrosine valine 237 COOH COOH Appendix III Sugars Some simple monosaccharides The β-D-form is shown in each case H H O H H HOCH2 O OH OH H HO OH HO CH2OH OH H OH β arabinose HOCH2 fructose HOCH2 O OH HO O OH OH OH HO OH OH galactose O HOCH2 glucose O OH OH OH HO OH OH OH ribose xylose 238 Appendix IV Nitrogenous Bases and Nucleosides NH2 NH2 N N1 N H N N N N N HOCH2 O adenine OH OH adenosine O HN1 H2N O N N H N N HN H2N N N HOCH2 O guanine OH OH guanosine O H3C O H3C NH N NH O HOCH2 O N H O OH thymine thymidine 239 Appendix IV Nitrogenous Bases and Nucleosides NH2 NH2 N N H N O N HOCH2 O O cytosine OH OH cytidine O O HN O HN N H N O HOCH2 uracil OH O OH uridine 240 Appendix V The Chemical Elements (* indicates the nucleon number of the most stable isotope) Element Symbol p.n actinium Ac 89 r.a.m Element Symbol p.n r.a.m 227* europium Eu 63 151.965 aluminum Al 13 26.982 fermium Fm 100 257* americium Am 95 243* fluorine F 18.9984 antimony Sb 51 112.76 francium Fr 87 223* argon Ar 18 39.948 gadolinium Gd 64 157.25 arsenic As 33 74.92 gallium Ga 31 69.723 astatine At 85 210 germanium Ge 32 72.61 barium Ba 56 137.327 gold Au 79 196.967 Hf 72 178.49 berkelium Bk 97 247* hafnium beryllium Be 9.012 hassium Hs 108 265* bismuth Bi 83 208.98 helium He 4.0026 bohrium Bh 107 262* holmium Ho 67 164.93 boron B 10.811 hydrogen H 1.008 bromine Br 35 79.904 indium In 49 114.82 cadmium Cd 48 112.411 iodine I 53 126.904 calcium Ca 20 40.078 iridium Ir 77 192.217 californium Cf 98 251* iron Fe 26 55.845 carbon C 12.011 krypton Kr 36 83.80 cerium Ce 58 140.115 lanthanum La 57 138.91 cesium Cs 55 132.905 lawrencium Lr 103 262* chlorine Cl 17 35.453 lead Pb 82 207.19 chromium Cr 24 51.996 lithium Li 6.941 cobalt Co 27 58.933 lutetium Lu 71 174.967 copper Cu 29 63.546 magnesium Mg 12 24.305 curium Cm 96 247* manganese Mn 25 54.938 darmstadtium Ds 110 269* meitnerium Mt 109 266* dubnium 105 262* mendelevium Md 101 258* Db dysprosium Dy 66 162.50 mercury Hg 80 200.59 einsteinium Es 99 252* molybdenum Mo 42 95.94 erbium Er 68 167.26 neodymium Nd 60 144.24 241 Appendix V The Chemical Elements Element Symbol p.n r.a.m Element Symbol p.n r.a.m neon Ne 10 20.179 scandium Sc 21 44.956 neptunium Np 93 237.048 seaborgium Sg 106 263* nickel Ni 28 58.69 selenium Se 34 78.96 niobium Nb 41 92.91 silicon Si 14 28.086 nitrogen N 14.0067 silver Ag 47 107.868 nobelium No 102 259* sodium Na 11 22.9898 osmium Os 76 190.23 strontium Sr 38 87.62 oxygen O 15.9994 sulfur S 16 32.066 palladium Pd 46 106.42 tantalum Ta 73 180.948 phosphorus P 15 30.9738 technetium Tc 43 99* platinum Pt 78 195.08 tellurium Te 52 127.60 plutonium Pu 94 244* terbium Tb 65 158.925 polonium Po 84 209* thallium Tl 81 204.38 potassium K 19 39.098 thorium Th 90 232.038 praseodymium Pr 59 140.91 thulium Tm 69 168.934 promethium 61 145* tin Sn 50 118.71 Pm protactinium Pa 91 231.036 titanium Ti 22 47.867 radium Ra 88 226.025 tungsten W 74 183.84 radon Rn 86 222* uranium U 92 238.03 rhenium Re 75 186.21 vanadium V 23 50.94 rhodium Rh 45 102.91 xenon Xe 54 131.29 rubidium Rb 37 85.47 ytterbium Yb 70 173.04 ruthenium Ru 44 101.07 yttrium Y 39 88.906 rutherfordium Rf 104 261* zinc Zn 30 65.39 samarium 62 150.36 zirconium Zr 40 91.22 Sm 242 243 European convention N American convention Modern form Period Li H Mg IIA IA IIA Actinides IVB IIIB IVA IIIA Tc Cm 96 Gd 64 Mt Cu Zn Al 113 Si 115 Md 101 VB VA VIB VIA VIIB VIIA IB 11 VIII (or VIIIB) 10 IB VIII (or VIIIA) 12 IIB IIB 13 IIIA IIIB 14 IVA IVB 15 VA VB VIA VIB 16 No 102 VIIA VIIB 17 Lr 103 I He 18 18 Rn 86 Xe 54 Kr 36 Ar 18 Ne 10 VIIIA (or 0) (or VIIIB) At 85 53 Br 35 Cl F 17 17 Lu 71 Uuh 116 Po 84 Te 52 Se 34 S O 16 16 Yb 70 Bi 83 Sb 51 As 33 P N 15 15 Tm 69 Uuq 114 Pb 82 Sn 50 Ge 32 Fm 100 C 14 14 Er 68 Tl 81 In 49 Ga 31 Es 99 B 13 13 Ho 67 Uub 112 Hg 80 Cd 48 Cf 98 12 30 Dy 66 Uuu 111 Au 79 Ag 47 Bk 97 11 29 Tb 65 Ds Pt 110 Ir 78 Pd 46 Ni 28 10 109 77 Rh 45 Am 95 Co 27 Eu 63 Hs 108 Os 76 Ru 44 Pu 94 Fe 26 Sm 62 Bh 107 Re 75 Np 93 Mn 43 Pm 61 Sg 106 W 74 Mo 42 25 The above is the modern recommended form of the table using 18 groups Older group designations are shown below U 92 Cr 24 Nd 60 Db 105 Ta 73 Nb 41 Pa 91 V 23 Pr 59 Rf 104 Hf 72 Zr 40 Th 90 Ti 22 Ce 58 Ac-Lr 89-103 La-Lu 57-71 Y 39 Ac 89 Sc 21 La 57 Ra 88 Ba 56 Sr 38 Ca 20 IA Be 12 Lanthanides Fr 87 Cs 55 Rb 37 K 19 Na 11 6 1 Periodic Table of the Elements - giving group, atomic number, and chemical symbol Appendix VI Appendix VII The Greek Alphabet A B Γ ∆ E Z H Θ I K Λ M α β γ δ ε ζ η θ ι κ λ µ alpha beta gamma delta epsilon zeta eta theta iota kappa lambda mu N Ξ O Π P Σ T Υ Φ X Ψ Ω 244 ν ξ ο π ρ σ τ υ φ χ ψ ω nu xi omikron pi rho sigma tau upsilon phi chi psi omega Appendix VIII Fundamental Constants speed of light permeability of free space c µo permittivity of free space charge of electron or proton rest mass of electron rest mass of proton rest mass of neutron electron charge-to-mass ratio electron radius Planck constant Boltzmann constant Faraday constant ε0=µ0–1c–2 e me mp mn e/m re h k F 245 2.997 924 58 × 108 m s–1 4π × 10–7 = 1.256 637 0614 × 10–6 H m–1 8.854 187 817 × 10–12 F m–1 ±1.602 177 33 × 10–19 C 9.109 39 × 10–31 kg 1.672 62 × 10–27 kg 1.674 92 × 10–27 kg 1.758 820 × 1011 C kg–1 2.817 939 × 10–15 m 6.626 075 × 10–34 J s 1.380 658 × 10–23 J K–1 9.648 531 × 104 C mol–1 Appendix IX Webpages Chemical society webpages include: American Chemical Society www.chemistry.org/ Royal Society of Chemistry www.rsc.org/ The International Union of Pure and Applied Chemistry www.iupac.org Information on nomenclature is available at: Queen Mary College, London www.chem.qmul.ac.uk/iupac/ Advanced Chemistry Development, Inc www.acdlabs.com/iupac/nomenclature/ An extensive set of organic chemistry links can be found at: WWW Virtual Library, Chemistry Section www.liv.ac.uk/Chemistry/Links/ 246 Bibliography There are a number of comprehensive texts covering organic chemistry These include: Carey, Francis & Sundberg, Richard J Advanced Organic Chemistry: Structure and Mechanism 4th ed New York: Plenum, 2000 Carey, Francis & Sundberg, Richard J Advanced Organic Chemistry: Reactions 4th ed New York: Plenum, 2000 Clayden, Jonathon; Greeves, Nick; Warren, Stuart; & Wothers, Peter Organic Chemistry Oxford, U.K.: Oxford University Press, 2000 McMurray, John Organic Chemistry 6th ed Pacific Grove, Calif.: Brooks/Cole, 2004 March, Jerry Advanced Organic Chemistry: Reactions, Mechanisms, and Structure 4th ed New York: Wiley, 1992 Volhardt, Peter K & Schore, Neil E Organic Chemistry: Structure and Function 4th ed New York: W H Freeman, 2003 More specialized books are: Eliel, Ernest L.; Wilen, Samuel H.; & Doyle, Michael P Basic Organic Stereochemistry New York: Wiley, 2001 Gilchrist, Thomas L Heterocyclic Chemistry 3rd ed Harlow, U.K.: Longman, 1997 Isaacs, Neil S Physical Organic Chemistry Harlow, U.K.: Longman, 1987 Sykes, Peter Guidebook to Mechanism in Organic Chemistry 6th ed Harlow, U.K.: Longman, 1996 An advanced text on biochemistry is: Nelson, David L & Cox, Michael M Lehninger Principles of Biochemistry 3rd ed New York: Worth Publishers, 2000 247 .. .The Facts On File DICTIONARY of ORGANIC CHEMISTRY The Facts On File DICTIONARY of ORGANIC CHEMISTRY Edited by John Daintith ® The Facts On File Dictionary of Organic Chemistry Copyright... NUCLEOPHILIC ADDITION to the carbonyl group of the aldehyde or ketone The first step is attack of the lone pair on the O of the alcohol on the (positively charged) C of the carbonyl group This is... permission in writing from the publisher For information contact: Facts On File, Inc 132 West 31st Street New York NY 10001 Library of Congress Cataloging-in-Publication Data The Facts on File dictionary