CRC HANDBOOK of tables for ORGANIC COMPOUND IDENTIFICATION Third Edition Compiled by ZVI RAPPOPORT, Ph.D. Hebrew University of Jerusalem, Israel cRo RC Press, nc Th 0 bbs6JNIVERSIOAD fe BIBLIVIRCA This husk represents information obtained fen authentic and highly regarded wwrees, Reprinted sera stcy of oferencen ae sted. Every reasonable elo data and information, bu the athe and the polisher can assume responsi forthe vaity of all materials oF for the con “gtd ith permission, ad sources ae inicaed, Aids fas heen make to give rel Allright served, This bh ray party theo, my mt Be reproduce in any form without Write comseat from the publisher Dinct all muir to CRC Press. fn. 2000 Corporate Blvd. N,W., Bea Raton, Florida, 3343 onmetly the Chemical Rubber Company Dex! Printing. 1472 Sal Printing, 1973 Si Printing, 197% ’ 7h Printing, 1977 ih Printing, 1979 nh Peeing, 1980 th Printing, 198 Heh Printing. (983 2th Printing. 198 15th Printing. 1984 1th Printing, 1988 Inston Standacd nk Number (ISHN) 0-8493.0503-6 orm International Sandatd Book Numer ISBN} 087819-303.0 Library of Congress Card No. 68-19660 rites ithe Une Staten Tables Tables HandbookJNIVERSIOAD fe BIBLIVIRCA This husk represents information obtained fen authentic and highly regarded wwrees, Reprinted sera stcy of oferencen ae sted. Every reasonable elo data and information, bu the athe and the polisher can assume responsi forthe vaity of all materials oF for the con “gtd ith permission, ad sources ae inicaed, Aids fas heen make to give rel Allright served, This bh ray party theo, my mt Be reproduce in any form without Write comseat from the publisher Dinct all muir to CRC Press. fn. 2000 Corporate Blvd. N,W., Bea Raton, Florida, 3343 onmetly the Chemical Rubber Company Dex! Printing. 1472 Sal Printing, 1973 Si Printing, 197% ’ 7h Printing, 1977 ih Printing, 1979 nh Peeing, 1980 th Printing, 198 Heh Printing. (983 2th Printing. 198 15th Printing. 1984 1th Printing, 1988 Inston Standacd nk Number (ISHN) 0-8493.0503-6 orm International Sandatd Book Numer ISBN} 087819-303.0 Library of Congress Card No. 68-19660 rites ithe Une Staten Tables Tables HandbookFirst Edition Tables for Identification of Organic Compounds Compiled by Max Frankel, Ph.D. Saul Patai, Ph.D. Assisted by Albert Zikha, Ph.D. Robert Farkas—Kadmon ENCE PRESS, LTD., JERUSALEM, ISRAEL, Second Edition Tables for Identification of Organic Compounds Compiled by Max Frankel, Ph.D. Saul Patai, Ph.D. Assisted by Albert Zilkha, Ph.D. Zvi Rappoport, Ph.D. Robert Farkas—Kadmon © 1964 by THE CHEMICAL RUBBER CO. Third Edition Handbook of Tables for Organic Compound Identification Compiled by Zvi Rappoport, Ph.D.CONTROLLED RELEASE PESTICIDES FORMULATIONS. By Nate F, Cardarell, MS., University of Akron. DIFFUSE REFLECTANCE SPECTROSCOPY IN ENVIRONMENTAL PROBLEM-SOLVING By RW. Frei, PhD. Sandox, Ltd. (Switzerland), and J. D. MacNeil, MSe.,Ph.D., Canads Department of Aga culture DRUGS AS TERATOGENS By James L. Schardein, B.A., M.S, Parke, Davis and Company. FUNDAMENTAL MEASURES AND CONSTANTS FOR SCIENCE AND TECHNOLOGY By Frederick D. Rossini, Ph., Rice University, Houston, IMMUNOASSAYS FOR DRU edited by 8. J. Mulé, Ph.D. SUBJECT TO ABUSE .» New York State Narcotic Addiction Control Commission, eta MASS SPECTROSCOPY OF PESTICIDES AND POLLUTANTS By Stephen Safe, BSe., MSc., D.Phil, and Otto Hutzingr, Ing.Chem. M.Se., Ph.D., National Reseach Council of Cama, MERCURY IN THE ENVIRONMENT By Las T. Friberg, M.D., National Institute of Public Health (Stockholm), and Jaroslav J. Vostal, MD., Ph.D., Uniersity of Rochester. 7 ORGANOPHOSPHORUS PESTICIDES: ORGANIC AND BIOLOGICAL CHEMISTRY iy Morifuse Eto, Ph.D., Kyushu University, Japan, RECENT DEVELOPMENTS IN SEPARATION SCIENCE Edited by Norman N. Li, Sc.D, Exxon Research und Engineering Co TRACE ELEMENT MEASUREMENTS AT THE COAL-FIRED STEAM PLANT By W. S. Lyon, Jr-BS., M-S., Oak Ridge National Laboratory “CRITICAL REVIEWS™ JOURNALS: CRC CRITICAL REVIEWS™ IN ANALYTICAL CHEMISTRY Edited by Bruce H. Campbell, Ph.D, J.T. Baker Chemical Co CRC CRITICAL REVIEWS™€ IN TOXICOLOGY DSe., DPhil, F.R.CPath., Chemical Industry Institute af Toxicology’ Edited by Leon Golberg, M.D., B.Chi ¢ inguiries to CRC Press, In. The present titled Tastes Fo) pounds, ic, sulfe the number of ¢ alkenes, alkynes, thoroughly revise to the third editi 8150, ‘Three tables: acids and organic ‘were also includes Explanatory these sections the preparation by tt references to their An index co the end of the boo added. ‘The main ob coy pounds. The bebo should as For further i books should be N, D. Cheronis, Analysis, 3 L. Meites, Handt F, Feigl, Spor Te AVL. Vosel, AT Co., Londor R.L. Shriner, 8 Compoueds, F, Wild, Charac 1958. ‘The publica of those involve part in the earlie the late Mr. R. Glazer for assist and especially | and gave many | ‘Thomas in ther Jerusalem January 1967ING vent of Ag ch Council, Da PhD, ricology PREFACE 7 The present volume is a revised and enlarged third edition of the book formerly titled TABLES FOR IDENTIFICATION OF ORGANIC COMPOUNDS. Four new classes of com pounds, i... sulfonyl chlorides, sulfonamides. thiols and thioethers were added. bringing. the number of classes included in the book to twenty-six. The tables of alkanes, alkenes, alkynes, aromatic hydrocarbons, phenols, nitriles and sulfonic acids were all thoroughly revised and considerably enlarged. In all, the addition of 2400 compounds to the third edition, raised the total number of parent compounds in the book to over 8150. Three tables containing the dissociation constants of more than 1050 phenols, organic acids and organic bases were added. Correlation charts for LR., Far LR. and N.M.R. were also included. Explanatory sections entitled “Explanations and References” precede the tables, In these sections the formulas of the derivatives and the full reaction equations for theie preparation by the most important methods, together with some essential details and references to their preparations, are given. An index covering both the names and synonyms of the compounds was added at the end of the book. An index listing the names of all tables and major subjects was also added. The main objective of this book is to assist chemists in the identification of organic compounds. The organization of the compounds in classes according to increasing boiling points should also assist in the search for standard vapor phase chromatography work For further information of techniques of organic analysis one or more of the following books should be consulted: N. D. Cheronis, J. B. Entrikin and E, M. Hodnett, Semimicro Qualitative Organic Analysis, 3rd Ed., Interscience Publishers, New York, 1965, L. Meites, Handbook of Analytical Chemistry, McGraw Hill Book Co., 1963. F. Feigl, Spot Tests in Organic Analysis, 6th Ed.,. Elsevier Publishing Co., 1960, A. 1. Vogel, A Textbook of Practical Organic Chemistry, 3rd Ed.. Longmans Green and. Co., London, 1957, R. L. Shriner, R. C. Fuson and D. Y. Curtin, The Systematic Identification of Organic Compounds, 4th Ed., John Wiley and Sons, New York, 1956. F, Wild, Characterization of Organic Compounds, 2nd Ed., Cambridge University Press, 1988 The publication of the third edition would not have been possible without the work of those involved in the preparation of the earlier editions. ‘The editor is thankful for the part in the earfier work contributed by Professors M. Frankel, S. Patai and A. Zilkha, and -the late Mr. R. Farkas-Kadmon. Thanks are due also to Mrs, E. Shohamy and Mr, A. Glazer for assisting in collection of new data, to Mrs. Y, Elmaleh for typing the index, and especially to Prof. S. Patai, who as consulting editor, read all the new material and gave many helpful suggestions. The cooperation of Dr. Robert C. Weast and Mts, F Thomas in the publication of the beok is gratefully acknowledged, ZR Jerusalem January 1967Contents Table Page No. No. Abbreviations pbBB5BERe . Ix. {Amino Acids Explanations and References to the Tables : 1 famines Alkanes and Cycloalkanes tee 1 29 | Primary and Secondary A Gases, Liquids, Solids Tertiary Amines Alkenes, Cycloalkenes, Dienes and Polyenes u 10-26 Liquids, Solids Liquids, Solids Icarbohydrates ‘Alkynes (Acetylenes) . um 2731 | Liquids, Solids Liquids, Solids {Nitro Commptfunds Arognatic Hydrocarbons bees Vv 32-51 | Liquids, Sotids Liquids, Solids INitriles . Halides Vv 52-16 Liquids, Solids A) Alkyl and cycloalkyl halides Isulfonic Acids 1. Chlorides, Liquids and Solids Sulfonyl Chlorides 2. Bromides, Liquids and Solids + ulfonamides and Sulfonanilis 3. lodides, Liquids and Solids - iThiols (Mercaptans). . B) Dihalides and polyhalides (non-aromatic) IThioethers (Sulfides) 1, Fluorides {acid Dissociation Constants ol 2. Chlorides, Liquids and Solids Solution 3. Bromides, Liquids and Solids Acid Dissociation Constants 0! 4, lodides, Liquids and Solids Solution ©) Aryl halides Dissociation Constants of Orge 1. Fluorides, Liquids | Solution 2. Chlorides, Liquids and Solids 1.R,— Infra-red Correlations C 3. Bromides, Liquids and Solids Far 1.R.—Far Infra-red Vibrat 4, lodides, Liquids and Solids Charts Alcohols . . VI 77-99 |NMR—Characteristic NMR S Liquids, Solids Hydrogen in Organic Strw Phenols : renee vil 91-128 {Miscibility of Organic Solvent Liquids, Sotids Emergent Stem Correction for Ethers... ... VIL 129-140, Thermometers Liquids, Solids Correction of Boiling Points tc ‘Aldehydes . foe Ix 141-160 Molecular Elevation of the Bo Liquids, Solids Molecular Depression of the F = “Ketones . eee X.. 141-143; 161-179 ] Carbohydrates Quinones oe cove XL 180-185 [Fatsand Oils 02... > ' Carboxylic Acids XIt 186-189; 186-210 Waxes Mix Liquids, Solids Diamagnetic Susceptibilities 0 Acyl Halides. . care XT 186-189; 211-222 | Four-Place Logarithms Acid Fluorides Periodic Table of the Element: Acyl Bromides, Liquids, Solids ~ Table of Atomic Weights Acyl Chlorides, Liquids, Solids Index of Organic Compounds Acyl lodides, Liquids, Solids Index listing names of tables a Acid Anhydrides . XIV 223.227 | Request for New Data , Liquids, Solids =) Amides and Imides. . vee XV 28-247 | “ Liquids, Solids bo Esters . XVE. 248-281 XN . Liquids, SolidsMe Page io No. Ix 1 I 29 u 10-26 " 27-31 v 32-51 v 52.76 1 77-90 1 91-128 f 129-140 x 141-160 141-143; 161-179 130-185 “786-189: 186-210, I. . 186-189: 211-222 / 223-227 7 228-247 1 248-281 Contents (Continued) Table No. Amino Acids XVIle Amines XVII Primary and Secondary Amines Tertiary Amines Liquids, Solids Carbohydrates XIX Liquids, Solids Nitro Compounds / XX Liquids, Solids Nitriles XXI Liquids, Solids Sulfonie Acids . XXII Sulfony! Chlorides XXIII Sul¥onamides and Sulfonanilides. XXIV Thiols (Mercaptans). . . . « XXV Thioethers (Sulfides) days XXVI Acid Dissociation Constants of Organic Acids in Aquequs' Solution : veces XVI Acid Dissociation Constants of Phenols in Aqueous Solution XXVIIL Dissociation Constants of Organic Bases in Aqueous Solution . XXIX 1.R.— Infra-red Correlations Charts Far LR. — Far Infra-red Vibrational Frequency Correlation Charts NMR—Characteristic NMR Spectral Positions for Hydrogen in Organic Structures Miscibility of Organic Solvent Pairs Emergent Stem Correction for Liquid-in-Glass Thermometers Correction of Boiling Points to Standard Pressure Molecular Elevation of the Boiling Point : Molecular Depression of the Freezing Point. . . . Carbohydrates Fats and-Oils, Waxes - Diamamnetic Susceptibilities of Organic Compounds. Four-Place Logarithms. Periodic Table of the Elements. Table of Atomic Weights Index of Organic Compounds Index listing names of tables and major subjects Request for New Data. Page No. 282-290 291-325 326-333 334-343 344-368 369-380 369-370; 381-390 391-410 . 41-417 418-427 428-433 428; 434-435 = 428; 436-439 . AgL-447 48-449 - . 450 451-453 454 495-456 457 437 458-465, 466-467 468 469-474 475-476 477 478 419.560 561-363 364 4 ilab abs, abt ‘se anh ad a alk anh, gu. asym. as bu bik boil bp. BP. be. be br Dns, oh lobe oo comp, cr cryst d 4,0, eri Selig ai, ai a, ld: DAL efor oth exp, ores fp, ee, LIST OF ABBREVIATIONS USED specific rotation acid nsoluce about acetic acid acetic anhydride addition falco} alkali amorphous anhydrous aqueous asymmetric blve back boiling boiling point browa, benzene bright ‘brownish cold bout chloroform chlorobenzene colorless compound concentrated corrected decomposes extrorotatory (or: D-configuration) erivative sdeliquescent silute sisillate dark cefloreseent cathy ‘ethyl acetate ether explodes from flakes Ayorescent freezing point freezes fom, ple lit ely eran, er, f hing hye. nye. yee ign insot he, eat, Is. ee lig Ing k. vs ime, meth i mod manohyd, mono mp. MP. need, nd, ot ora. lore forth loxid Ip pa par. pet pete, ph. [ph hydra. PANO, nh. powd fuming elacial alitering elycerol granular green hot heating hydrate or ydrotyses hyeroscopie insoluble ‘enites insoluble levorotatory (or: Lvonfigur tion) leaflets microscopic milliliter ‘modification monohydrate monoclinic melting point needles ortho olive range ordinary organic orthorhombic oxidation para pale partly petroleum petroleum ether phenyl pphengt hydeazine hiteobenzene plates powder br purp. pyr redsh thomb, th, sh sh. ld sot. sol, soln, sol stab, subl vm tab, tab rete tol. hk, wel vice volat wt wh, yel els, gts xsl prisms purple Pyridine (or: racemate) rectangular recrystalization reddish thombie rapid rapid heating soluble secondary scarcely slow heating short slightly solid slender small softens solution(s) solvent(s) steel stable sublimes symmetrical tablet(s), tables tertiary tecragonal toluene transparent thick clinic ‘unsymmetrical unstable very variable vicinal volatile oF volatlizes ole “ white yellow yellowish above, greater than below, smaller than miscible syleneoe ln EXPLANATIONS AND REFERENCES TO THE TABLES The following section gives explanations and references for the preparation of the derivatives appear ing in the Tables, Formulis of the deriv ves a6 well as the main methods for their preparation are given Usually. only the reagents and the solvents required for the preparation of a derivative are mentioned without specific details for the reaction conditions and the exact procedure, The aim of these notes is mainly to enable the worker to choose the method preferable in the conditions and the feagents available 10 him in his labora tory for the derivatization of his specific compound. However, THIS IS ONLY A REFERENCE SECTION, AND NOT AN INSTRUCTION MANUAL AND THE QUOTED REFERENCES SHOULD BE CON: SULTED FOR THE ACTUAL PREPARATION OF DERIVATIVES, ESPECIALLY REGARDING SAFETY HAZARDS INVOLVED IN THE WORK. References are usally given far the preparation of all the derivatives having separate columns in the Tables, as well as for important ones listed in the “miscellaneous” section of the Tables. References to five different popular analytical textbooks afe given, assuming that at least one of them oF another equivalent publication, ‘would be wvailable to the worker. These are N.D.Cheronis, 1B. Entsikin and E, M. Hodnett, Semimicrs Qualivaive Organic Analesis, re) edition, Imerscience, New York, 1965, quoted inthe text us “Cheronis. R.P. Linstead und B, C. L. Weedon, 4 Guide to Qualitarive Organic Chemical Analysis. Butterworth Sein: ile Publication. London, 1986, quoted in the text as Linstead RL Shriner. R. C, Fuson and D. ¥. Curtin, The Ssusemanie Ldenttiation of Organic Compounds. th inion, John Wiley and Sons, New York, 1956, quoted inthe text as "Shiner. ALL, Vogel. A Testhook of Practical Organic Cheoystry, 3d edition, Longmans, Green and Co.. London 1987, quoted in the text a6 "Vor P. Wild, Characterization of Organic: Compounds, 2nd edition, Cambridge University. Press, Cambridge 195K, quoted in the text as "Wild Im addition, leading references from the original literature are also given ough the literature cover- ‘ge is not complete (especially forthe common derivatives) it was attempted to describe diferent methods, and to give as many references as possible to less common derivatives having limited scope. More references can be found inthe textbooks mentioned above Derivatives appear either in a separate column or in the “miscellaneous” section in the Tables, where separate columns are usually given for derivatives which should be tried first, and for which enough data are available, Derivatives which should be tried as a second choice, or preferred derivatives For which not enough data are available appear in the “miscellaneous” section. The explanations and the references for the diferent erivatives are artanged usally in the same order as inthe Tables. Occasionally, this order is changed in the explanatory notes in order to deseribe the derivatives in a logical order (eg. in Table 17 the phenylurethane appears in a separate column, while the phenythydantoin appears in the “miscellaneous” section: in the planations and references” section the phenylhydantoin appears directly after the phenslurethane). Derivatives which ate followed by an asterisk are those recommended for first trial, Other derivatives should be tried after these [Although “Ae usualy stands for monovalent aromatic group, we used its few times in the following sec tions asa polyvalent aromatic residue. This was done only for demonstration purposesEXPLANATIONS AND REFERENCES TO TABLE 1 ! [As a eesul oftheir inertness no general suitable derivative exists for alkanes and eysloalkanes, Charac: terization is based only on the physical constants given in the Table: melting and boiling points, index of re- Fraction and density. Any laboratory text-book will give adequate directions forthe determination of these con- Pala 3] Propave 4 | cyora, 7]22-Dime * crete 92.1Dimet 102M rene 12 tee 1a] Mette: L 1s|eieheDi p 16] Spropet 17 | cycopen 18 22-Dimet 19 |e 20]23.Dimet 31 2a na] satan ast 24 |rctenane 25] ragleyle Mebyige 220m 2A-Diet ethers 22.8.7 3D raeet.b Seyi Jousdiye i tere) : 41 |attepan sn) 22atteia 43)cietz-De 14) Menyioy 45| Eile 46) 113.40 45]25.0ime 19) aronea, s0|240iee 5i|223-tee 2] tyra, 53)33.Dime sa] 2aacten . sslutate i so) 28st ‘ 1]23.ime 8] Sa sD wT = ingle WARNING: Thisisnoanistrction manual, References should be consulted forthe prepuaton of derivatives 2TABLE I. ALKANES AND CYCLOALKANES 1) Gases and Liquids (Listed inorder of increasing b.p*)* tolng = ‘ening ; > No Name | “pate evi v8 os 1 [atone a ~iaa 2] Ewe ah wat 3] repane or cin 0038 4] Cydupopane =e Tine om 5}: Mathtppae buns) Tin | lise ast ' ‘Jeune | Too ids ‘ane osm? 5] 22 Diowinigopee Neopets) 9.303 ie38 aa soiat 2] Cyto hos 125 “30 Ursa oom 9} hsDimetnydopopne does “i089 168 ase 10] Meters mast i399 3a aise 11 one bmesteycoropane » tins oases A 12] Ettocgrensee Soe “iwi ne can ! 13 etenne eon Tim ase oie i te Settee bea | 130 eons { 15 at Dimeyy cpap iin ‘2 oaozs I 16) Sotopntone jon “into Lato oss i 17 eSepenane om sar ‘tes nese i) ts] 23-bimemboae pm soar tee seme y 15] itartimetpecopopane sore ‘ai cea 10 22:Dimetarne Soom ise Laos Cestee : 31 [2stemnpenne com tse vines assis ses ienane om is ast 21.25. tamestytpranme os Uses pres 2 rtieee on sai tase Sssosr 3s eamtecourne ‘oes “ass tat. Som 26 aedlcopenne ma Has ‘io eu 39 22 Din iene i] shan ies oars 44 |2aDinety etn ms Tie20 tas rz 33 [conan ron ose toss oass 4ofa2a-tamesue toa <9 Laie oaoon 31] 33:Dimetypenane ee rake 12 dnt 32) -Dimeepopetane Saas “os 1asse onstes 33) 22:bimctyienane pre ‘se 9508 52] 2xtamocane soos | iiaate tase tes 3 fom bao Vosse oan 46 eset. sins Isn97s Uston m0 35] Senge | Vit usr 11] one Dim ecpcntnne ose iiss tata osha 25] Sipe ous tise tsa oasnie : 40 eatin Quadro. 0°"0" * taser fy ‘ee 11 etepone sar -9061 Lanse osens £12 |22.8tvmeyipntae sam ary iss fine : 43 eset Dimetsesopemtine wn “S490 tao ome 4 | etseyconevane veo =i26593 aie ox8%9 4 [Easterns tose Thee "Sioa yee? | 4 |iatastinete dora toaaes Tina an Sens {9 |22:Dimeesane tna rhe ‘os oan : £825 Dither {00 03 a0 ‘one O.nise i 45 | inmates meta pn | tos2y ciazs | tate onen i 50 24min tote Voss on36 51 |223-tamcniecine voaat aa ates ote ' £2 furan tet Print depen tia u1a30s tate oass i 5 |33:timcniecae Nise “het 1009 oie i 5: [234 timayiene hae Stor vano> 71506 55} 112.trimedhyeapeane ina» at rpc) on j So) 23-1rmanhenane ase woo | rs o32619 57 |ta.bimwcnenone isaor or nists ' 53) sumrmetnpenane iss “tse oni98 : ‘Derivative date given in order pty color, sven from which eal S07 = teiplepoinsS)— ataturstion prosureTABLE I. ALKANES AND CYCLOALKANES. ‘ 1) Gases and Liquids (Listed in order of increasing b.p.*) (Continued) Boling Meting i OF wo No Name cr ce nw be 59] teed ran: Trimethyleycopeat 11631 | -snss Laisss oes 118] s4-Dinety 60) tedsnane-A-Timetielopenta ns 11, vy 74 us] Seats 61] 2 Mtebytheptne ni76i7 109.04 1 ouo4 49702 120] Eye 62] xtestiepane Ti) = 120955 Vere 70463 , 11] 2334ter 653] S4-imety texan unm e008 i923 1221 73.Dimety 4 teweneisn4Trimethylesctopentane M8 ian 0766 123) yanst234 65| Seni-S.nehypentane 118299 90.87 vanrrs D7 ; 124] etsopropy (| Sethgexane nas ta0162 D738 125] ¢Mtetnec. 67] SMerhyheptane rigors “i203 1398s 0.70880 * 126] Lasoo | Cyctoeptane (Ssberare) 18-20 A198 ras ogn7s 12] eae | ranch Dimethyleetbenane 19381 6962 12000 0 7055 12s | eategact 70) 1-Dimethyteycloevane i9.ses 33.495 142900 0.75004 : eh 23-Te 71 cic. Dimethsleycabenane ‘08s asi Lane 0.76603 Eee 72) tan L-kahytmethseylopetane ox =08 16 07613 26-Tinet 32) rns Eby} 2metheylopetone ni Lag 0.7690 t shat 74] cont Ethyl methlcyclopemtane bia 103 om SD.olp 75| Lethyl--methytey pentane rs “iia nats 0.74003 q 22 Dimety 16} 224: Tetramethspentare naa 66.58 40588 ones7 © 135] 22.4 Tme 77] teiedoie Timer escopentane 0 riea3 14282 ons 136]2248 Ter 75|rane-.2-Dimebseslohensne } aa 88.198 Lanes 0.77601 1ai|228tHea 73]225-Trinetsthevane 184 10578 Laven orm t 138) 22.6 Tiinet 10 cit A-Dimetyleyctabexane J 2aszt 87.436 1a3%66 0.7985 139) 223¢Ter 11 | ran} Dimehyeyelabenane ras 90.108 aso 072 14 Nopinane 7 82) mOctane 125.548, 56795 197 os 141 | ane Ey 83] fapropylectopentane 649 mats Lanse 0.7653 142] Cyloctane 48) 22 Trimebnbexane 12554 109, 14033 O7156 133) Eta 45] cet eanytemetyleycopentane 128080 10598 149933 078522 1 | oNonane se] cin a-Dimetytycabenane 129708 soon 14596 0.79627 145/13. | 47) 2,44-Trimethgherane 1038 <11338 Lars ont ‘ 146 rants 14] ocPropsleyctoentane ao ue? rane | 0761 warlinta as t9]2.35Trimenpthexane iM is 14061 7219 as ict 90] Eanyeytonexane L788 =a rasa ose 139] 25.6 91 | 2.2-Dimethyheptane 13269 30 ‘oie 710s 150] 244Trine 92| 2.34 Tetrametylpentane i016 =i2.09 aura 0.73895 . ti fzsaster 93 24 Dimehsteptane ms } 4033 one 132) 2244Ter 94 Metiteclteptane ss saaio 03082 153] oprpyey 95 | 22acTrimetnsnexane I6 10s 07292 Isa] asset 96| Et 2omettnexane 18 16 ons 155 |22..4cT 97 |3-Etyt22-dimetiypentane 1a 92 vans 0.7348 : 156] 22-Dimey 98 | 44-Dimetbyheptane 1352 14076 0705 1s? [snipe 99 |24-Dimeth heptane. 1521 129) 07 0.7089 153] 33.8 Trine 100 | 2S-Dimethytheptane 1360) 14038, ons 4 159] 2.36-Trime 101 | 5-Dimetytheptane, 1360 08? 073 160 |24-Dimey 100 Bieyctot2.0}ctane 180 ats oxsts 1st | dveictem 103] ceieyet(3. 0) 16 65 asase ossise 7 162] 4128.0 to | 2-Dimethy--thyipentane 13678 12 tant ons nasser 103) 11.3. trimetyleelobene hrs 1362 868 Bets 106 3.3-Dimetiytheptane. B13 13085 as Pepe 107] 22.5s-Tetramethtbexane 75 10580 ansas 23ST 108 | 23.3 Teimet 13768 “ies has a3 2:Dinethy 108 | Sy) domed be 14120 0731 assem 110 | ranr-1.8S-Trimetyleycloexane aso 142404 | 07720 2-binet, 11 |23-Trimethsibexane 190) atee 07392 22..rime 112 |cteh3.ScTrimethsteycabexane 0-05 1.430105 0773 2-4 bine, 13 |tran-h.2-Trimehyleyclabexane vot LIne om i 22-bime ig |223.3-Teramedy pentane 027s “59 ver) 075666 p2sdan 15 | 4k -3metyInexane 04 Las om : 116] 33. rinetiy hexane a0. ae rain | 117 [23-bimethsthepane Les | 408s Derivative data ven onder ap ysl color, solvent From which yale "Derhatve daeTABLE I, ALKANES AND CYCLOALKANES. : 1) Gases and Liquids (Listed in order of inereasing b.p.* )( Continued) DP Ne Name a ne Py a : voit" paint" 8 ores 1s sabia wo van) rae ones U9] ska settee oe va ov ots 12 seep uaa 1 on rout . 12)|23.cerametipnane Pe Shans van orsis ons (23|2.:bimcty inane va 1 tse oe 133 [imme eaten base 1H ysis ore ; 124] gro Saetey epne (Pigs wea tase amne- ons 135] sntailocae vas aires owt otis ons #16) hepeptmesecoentne as Lao opm ous 12) senrepe | ise ts oan orass 138[ zante Vibe “tos van opi oho : tio|eeka-tameiaieane tat "te orsi0 ox 13 Stace Naas ins ‘ase Siam ovate 13)| 2a Tmeag pane | ‘ot ons oto 1in|eectaatmeastecieare tte ‘sane O78 ; 123| 2. biyientce Use ci ‘est oasis 134/22:Dimey-terhyteane ‘a ian om 13s] 22Trmenmepane tha os ons 1ao|2asctaramtesan na tai Oise 151] 22.trinenstepane ve tos one ie] 2aeteeyen tia Vos oniss fis |22..ctarametheane taba Ve on Ho] Nopane (MDa hepa) =| 10" vist thet 181 |amsthttmctseoerne We90s-15 “a0 toe orm 123] Craven sof io wan Us oh 13] age meaieeane ae va on 0.78522 144 n-Nomane 4} 0.81 = 53.519 | 140542 0.71763 oer 145|1.3.3:Tmeiy2.2. heptane (Fichane)- | 18-2 tae aus ou , 146 an a 4mtecteane Iie te oom ons! Ui |ectaeanetycssne tes va oss ony 1a etka aes 1258-00 von a trom is [285 tamatnepane las Ui oe {S0|Rtactmeaeyane ‘ ta os 1st |23.terametsnnse in Lise ee 2 Aicteramesteane tsa hm O70 151 oon tas wi (oss oma Ista eta so ve ome iss[2eacen jo iste the ors : 156|az-bmetntocane | is ose ors 155 |S. ewane iss as ons 15 ne roche Iss | van on \ 13 aasctemeapope iss thas ons Vo aching isshoo | 10 ong 181 ddcrety ach doesae tis tite outs 182]4i2.Simetotane ray ato on 164 [etrcoeaase tess Ciara} Lie orate roieoorne tsar “ato tes pss oners ‘te |A8 intnepe is tite ont oss 162m tte. is tite ome ont 165 [24min ts ‘ho oa ohm 169 | toimeyheprepietee is ties otsk0 one 1 |22sctimeniiepane is var one om 17 2cbimea-ttbesae se aie on om : 172 23-Dimentahexee is he ote ors 115 fractions ts ‘ine ones one , 11 |aattarmerntece ise 1 one nas ; 175k met eptne ts Vane oh on 16 aa.bimcy acta 199 "ow one Derivative data given inorder mp ,crywalsolor solvent fom which aywtaliaedTABLE I. ALKANES AND CYCLOALKANES. 4) Gases and Liquids (Listed in order of increasing b.p.*) (Continued) x Tpoig wane T ° ame point. °C point, °C | ba oF No 171] se inet | Tans" apse 3] ont 178] 38 bimelomne. | to eerie ee ‘omen 179] hsopropytheg | 160 | {sai os ans [spine tto|23.¢Tmcynepae | to | tan ouae mul tdaecte {st 4 Eayt2metytheptane | 1 | {tas nae 235 [Canosa 182 | 2,6-Dimethyloctane. 160-05 | 1 1403 0.7285 236 | Ielsopropy!: 1832223 Tewumathessne } teas ais ose pifotaasy 184 | rans-1-Lsoprepyl-4-methyleyclohexane ) } 1.4393 | 0.792 138) [-Mefagt tr stented) | 2 ebene intone va tae | our 2a] seme 23.45 taraeiniheane ts iat ast 2 fost S-Ethyt-S-methy heptane tot 14 { 0.737 242 fa Pentyleyel 53-Dietyinine tei tes O80 25 rte {Sbimciytcne te ia oes 23 rare tah Spmnces bmn tease | ie 2en| tater atime | asso eas dei fntadee SS tevametshesane | ies | led eres 202 etna |3.3-Dimethyt-4-ethythexa J ws | 0764 263 | €betyteyelay s'stettinonane fos. pa] | oars 264 frettee 210 |4-Methyinomane | 6s? 987 | re Teradeat 2 166 ) | . | n-Nonyleyeie ae ‘ee | ocala 2 tie-ssm seroma 2 fcctpropS-nci cbse a? eben ilmentn) Nene 21s p23 remonctsipeane 16. L606 dc 3s frosts termetteleane Weed e0 1th ebro 51? sarbitthxane tees a) Patsy 218 Mette wees fas] me ete 20 [ebro mt dehane | te ie annie tee dimen | Srt--mcinytepane } ser un | os tis -mcytepane ter | } ide oa {cette so) ae ji oo = staan | terse | tans taser Dera xem is wi Vans oat tiie tat tae 00 fetish ta tae faa Scere ‘ot tie | aan 25 |et-haproptsmetiecbeane icin] ak Ss cose 2 |cintitopoptmatyhciieane ters tas [bate ‘tpt | | 200] dct. temmeteclobenane ves 70 | assem, | ois 351 25-DimenytSeayhecone @ var” [odes ‘Derivative dat given in order mp. etal coor, sent rom which esalizedTABLE I. ALKANES AND CYCLOALKANES. a) Gases and Liquids (Listed in order of increasing b.p.*) (Continued) 5 ae el Re) J 233 pectin woo ris dans oe | Sanat pe Me | oka ees I rep 8 Vie oe q n-Uindecyleyetopentane(n-Hendecyleyclopentane) 296. 14303 08135 0783 - aL 0740 ‘ one 08166 ——TABLE I. ALKANES AND CYCLOALKANES, 'b) Solids (Listed in order of increasing mn ye Ne None ‘ing Tine 2) rttexadecane (Cenc) 8 28.29% tos20 dlecoberane | ass us 5 mtetaectne 2h sors 1 726 6 Tetradecpeytaterane } ™ | 3] Hence coentane 2B | meats | dee saad j P28 | Petadeesiylhenane » 10] Otdesteapetne x» Ii] eNonadenee m1 2a whe 12] Hexateoeytterane ne 13] Nouadecseapetne 3 | 14] nteocne 368 3a re 15] Hepadcteyctohenane ms 16] Este ylpetane os 1a] Hendon | ws i365 15] Hennepin 2 20 rDocosaee | saan ses 21] Dacostecopestane 4s 32] Nowadeleyclohenane asa 13] trcnee | ns ‘io 25| Tiong ® = . | mw 2 Tercoyey tape ‘I 28} Nenicosseycoheame Sts 23| eencinane 33 ‘as 30] Prtacoseyclpentane 31] Docoseyenetane sa 32] Heaaconeylopentane % 35) Noreyelene Treyelok22 LO Theta) % ioe 7 1] ettenacnne sos sin 19418 35| Cyeebecadectne 9 oe 39) Hleprcoricytpentine. % 58) Htpacosane so ‘ai 39) Tewacoseytoeeane sos 40| Cycopetaecane wt 41} Octaceply copie ia ‘| nOetacone i ak 208 43] Pemtacsseyttenane is 44|Nenaconteycopentane @ 45| Neenonane a ox: [ime naasye hase Last: 1 at68 Lasso" 14191 ron 109i 145960 0" ate vaso? vaio 146020 Lasse 1.408 ‘tet 463 ta vaez7¢ tase 108 ai0% sore Tass 145352 1a5iig 1439205 L467 130" tsp eto o7re7 0 >. ors 7780 ors O7i9@ sa0re aa arsssit ony 07580" 787 os290p 8276 0.2000 0428 O63 osn107 059698 ossise assy osn267 0.7695 osni2e ons O26 om son ose 0.050 ose ges 083397 assay Ossisir Danka Derivative data given inorder p77 olor salvo rom which sali. ss = undercooted uid 2s Te 15] tracont, 53] ocacope lems oles 2) zeta 4 Patines 65] Penatrace | Dotriacan 61) eran (| Henan 9] Tracom 70) Hepatries 11 teerice 72] octaiacon 173|Pentatnen 14) Noein 15 | Mesaacon 176 Teacnin 77| Norberane 18/2233.Tee 29 Berane: ‘0! ——_ Derivative da =U undeco», ona oom ose ons a omni" oxi si 07809 om sine” or Ossi ane orss0" oneTe asso osm’ oases" a9 oxsog an omar ou 7 O79 ois anwse mel oan ox ost" pase ons omer? oss a3 | 4 TABLE I. ALKANES AND CYCLOALKANES ‘order of increasing m.p.* ** (Continued) bs Solids (Listed i 47 [Teaco eytopentene 48| 4-aobornane 51 Hentctaconlectopentane 53] Octaosteycabesane 51] Dowiacontteelopentane Doteiacontave (Hie) | Nonconpcyloensne $9] Teaconsleytabexane (60 Teeatraconsleyclapestane 61 | Tetratincomtane 62) 2u-stetntnonacosane 63 | Hteneiacontleyelonexane 64] Pentatriaconslevelopntane (6 | Dowiaontteyctobexane 67 | Hesatraconslesclopentane (5 | Hevatracontane 6 | Teiviacontteycoberane 11 | Teraiacotyeyclohenane 172] Octaciscotane 15) Hexawiacontleylobexane 16| Teracomtane 11 Norbornne (Hsyle(22. heptane) 19 | Borwane (Camnphane) 10 | Adamantane “Derivative data given in orderim pry color sole om which crystallized 1U = underooled gui. point "¢ 9 ” 763 mt 100.68 158-9, sa Bs Oe 9) fee aha! aes ta 1a 1a 146536 16st 133509 \ 146s Lasstg 1 sort 1465 14500 as Lasse ae taer09 Las 1a Lise » oisne O30) osn7sre 0309 Danse psig 3408 on oan4y ossraq Os6sy ossg oe" nisi ass7se asiste anes ose ossese a8399¢ onisre osanzp sans onndigEXPLANATIONS AND REFERENCES TO TABLE II Bromine addition compound* CHR’ + Bry + RCHBr—CHBIR’ Bromine addition From the alkene and bromine in earbon tetrachloride, For directions and examples see: Chetonis,p. 576; Shiner, p10. From the alkene and bromine in water ‘See: Vogel, p. 281 From the alkene and bromine in chloroform, ‘See: C.G., Schmitt and C.E, Boord, J. Amer. Chem. Soc. 4, 751 (1932), 24-Dinitrobencenesulfnyl chloride addition compound.* No? NO: RCH=CHR! + on-{ sa + ReHCI—cHt )-0, 2A Dintrobentenesleny chlonde dot rom the alkene and 2,4-dinitrobenzenesulfenyl chloride in glacial acetic acid For directions and examples see: Cheronis, p. $77; N. Kharasch and C. M. Buess, J. Amer. Chem. Soc, 71,2724 (1949); D. J, Cram, J. Amer. Chem. Soe., Th, 3883 (1949); N. Kharasch, C, M. Buess and S, I. Stra shun, J. Amer. Chem. Soc, 74, 422 (1982), From the alkene and 2,4-dinitrobenzenesulfenyl chloride in benzene or in carbon tetrachloride ‘See: N. Knarasch and C. M, Buess, J. Amer. Chem. Soc, 71, 2724 (1949), ‘S-Alkylmercaptosuccnicagid * R I HSCHCOOH —_—_RCH,CHSCHCOOH RCH=cHR + | = CH,COOH CH:COoH SAlkglmercaptosucsnie sed From the alkene, mercaptosucinic aid and benzoyl peroxide in methanol For directions and examples see: J.G. Hendrickson and L. F. Hatch, J. Org. Chem.,2, 1747 (1960), Maleic anhydride adduct (from dienes) = co, NoHo, oH cH-co™ cH _cH—com™ rom the diene and maleic anhydride in benzene. For directions and examples see: Linstead, p. $1; Vogel, p. 943 From the diene and maleic anhydride in xylene. ‘See: Linstead, p. St For general references see: M. C. Kloetzel in Organic Reactions, Vol. 4 (Ed. R. Adams), John Wiley and Sons, New York, 194%, pI: H.L. Holmes in Organic Reactions, Vol 4, (Ed. R. Adams), John Wiley and Sons, New York, 1948, p. 60;. Diels and K. Alder, Chem. Ber., 62, 2081 (1929), Nitrosochloide adtion compound. RCH=CHR’ + NOCI -+ RCH(NO)CHCIR’ ‘adduct "Derivatives recommended frist i WARNING. Inve notaninsruction manual, Referenes shoud be conslted forthe preparation of derivatives, 10 From th in ether-aceti Fordrec From See: M WaRNISEXPLANATIONS AND REFERENCES TO TABLE II (Continued) From the alkene and aitrossl chloride (prepared from sodium nitrite in concenteated hydrochloric acid) in ether-aceic acid miature, For directions and examples see: Linstead, p. $2; R. Perrot, Compt. Rend., 203, 329 (1936), From the alkene and nitrosyl chloride (prepared from thionyl chloride and nitrogen trioxide) in ether See: M.Tuot, Compr. Rend, 204, 697 (1937). Chem. Soe SL Sta. Wiley and yand Sons, Derivatives recommenced for fst ia WARNING: Ths snocaninstrection manual, References should be consulted forthe preparation of derivatives uTABLE II. ORGANIC DERIVATIVES OF ALKENES, CYCLOALKENES, TAB DIENES AND POLYENES a) Liquids 1) (Listed in order of increasing bp. | ‘ ome) we a [oP 1emene aise. |otonat [1st fase fae Yustas Joss — fuse fate eee 2} Breen Proqsinss. 770 | 1¥825" sty fie tation [Ss fisaont fons i 3 Celgene Se 4) Aline pas feiss enn iw isms "fea ' 5] Metvprpene ---[-690 [otanas faster Jose fie [ido md [1595 [2.bimerophe “allen chlonde sor 6 tetaene wwsis fram ososr fae [isos sia [17951 fr Dironbes: len rd, 29 | -readine mses ‘Eibytere a) napuadone f4sn — Jevons jroo [oenss-s Ja ste sofa. tumaine 630 . Dinette! slirasarpatene.....foss — | -tosss owt [a free usnio fuse 3) |e 5) Crdotaere ba one 1 10 eaeBetene bre [tis cane {4 isi fis N[izaaaiee flows fta619 |iko08 [ous ere 2 Prana fo sons 7 _) itemise . . len 3] baeayeceyens 12]2Memyttbutew [soa frenao Jseir fowra fan far > so fren ae fiaeteaadiene 597 [otanan [ie ]o.706 fre isa, au] 2 dimen « 235] EM pee 14} Peto bor [rosa frariss fooioso [ac [a sore [192% | Merseponesinic ae edad EMfeyhete 10736 es isfaataiytrdiene...faiie —[ousrse fae fous: fae farsae rises rors |aercpeosccinic Bees) sod adduct pire are 30 1S Henaine Jo) sateiteetatatene, [32 100s ‘aah 15) 2atanat ior [oaisos szien fois fa [aoe Mui nh dct, Breese thea pron tune | 155 8 ale : 138, 20) teen 18] rona-ponine ... fiers [igor frame foo |i soe [rion Io]emarenne fas [iste Tiawo fowsse fae foam tists fast ao] tatamitete: 1 sist fos faene | eset tae aifaatenstzauire .fixsr— |-iss77 favs foes Ninosochorid, 7 fet ate Merctonuceiie | sone aid wdc halen iss a0 15] Seven cre 22] satemttzamae to aio Joos — fren [iso 2 vsaa [aos ate ene (1.1 Dinets , fa eer Sieve 57) 2M pene 23] cveopenatice. foxx [oss fhasve Joes Diner 2; Mali inked ot 5: Benmnqinane 4 45[ sateytran aaa 6 ee Ls Pemaden 11 fea fam foasos fr ss. Makiewrh, addua, 9] awed Herne Atinersine) ispet eth: Ov el rueaae by Kino, iste) HOO! + si) atest CH.cooH 52] 23-Dimepht. 25] 2..Dimettetone -usz [uaa Joos fa fos rior [assis peas 5a 53) ca.teaee 26) taranaetonadion 41203 |-ars7 Jaws Joon frm fast risa el cena 2] rectPemadine for |otson2 flies Powsin free fase fiscal peritees ‘iene Derivative dtapvcn in weer mp etal aor, sven rom whch sane 55] stent +7 tile post: s = at satuaton prewar enews SDamatve cageENE: TABLE Il. ORGANIC DERIVATIVES OF ALKENES, CYCLOALKENES. DIENES AND POLYENES a) Liquids 1) (Listed in order of increasing b.p.)* (Continued) ‘ales hod 2.4-Dimirophens ‘eles horde Metupisuscinie asd adds, 1 | Mercipionusinis ssdaddec iver) Dimer 32 Mae sh dust, 8 SHenrquiaone ut 18 6 Matecanh ads ‘pet eth: Oud by KMn0, = Hoon + cH,coon 28 |essopemen. 2 20 12-Pontadiene S136 32] sMeittpentene [18 33] SMetyLtpentae (5S ‘ene yofedterisici-a” (so a Metisiincd—|s4.ss wai 30] 2-Methtctpentone 60.7 40] 1Hlesene Jess 41] SMetgteyctopntene s.0 44] cob Hexen es 15] Sttexene(ccirone [666-67 46) ran Hexene. [67.08 47] 2Mteny-2-petene 48] aatetgt rans 2 49) ramcb-Hevene. 60.87 30] 2Hexencitrane 6.9/8 mature) si] 23:texadine ot 52] 23.Dimear js.78 atadine 53] cea-Hevene. esse 54] 12pente 70 ene) ss]ametiiciea —froas Isso 2139 [fine | rea 42001 son | | Nas 1.012 13a oveso2 | over |e { oonsa fa osm ar ovsos fa ons [ar owns [ae oom {a asia |e one de | rer 708 oosns fa ope 1060 fr e016 oo tsios— |ioo3s ey 1.3060 |isoas | sr Jrsois fuser 89-90" Vso [isa iv . rsos {16027 me 1.5085 0 rsms |. sei2 138. be, on sms [ise na 1 sos } ecaddet 124 3.1 Pcie Pevbenoic acid out epony ‘selopentane, bp. t0r | tore-o DAL HNO, sue ‘lft hr, 1 2 Merapto seid ade, Is "Derivative data given inorder mp ctstal color, solvent fom which esac 1BTABLE II. ORGANIC DERIVATIVES DIENES AND POLYENES 1) Liquids 1) (Listed in order of increasing by OF ALKENES, CYCLOALKEN’ )* (Continued) wee Se faatamiasgenae fo has orn ‘w[eammean ee Teta anes me) |e 59 |e. faa je forest ree ayos-4:0) aoe orm te 29 sleeping haa fas isos fosser a are tayo sia» |Mercaptsscinic — I | ta 190 | $9] icin cane ass laos cade } | | ofp imisiztine fr ]-72% frano> foro — fae many Sftimmicormene pss [Siar fs [ose 64 2-Methytters and/or [76 1 446 0.719 8 rouretedoe. | 4 6{\2ieatioe je nazs2 for frere [iso seo fassns Prostate) 85g peat 66 [zation andor fs fis fons 46| stent taene reat | 0 eSteachcspne | fs.8 fuast Joos 5 Maas tone | sve sslaevctptvance rs [visas ftom foome fa faze soto fissoe 85| Mey stexe ‘veneer 2 | kDimane as oo |sbmeayte bse sea fave foo fae fos ssi fuses pasa vate | Spates rofsdartvinaayti.” rar |-ro0as fram foro fa [owen {ovo sol Stem texa tone 71 [aateyit spas po. tame loz 91) Dime. 12 Jerome Herat 5; nassae |oanang fren 1 sei has ‘nnce bes" ast fore enc an fo.70 ras’ lois ne os] omic hes fer rasa forse |a.sar rsum free |oaicam, aden, a ne ee we 0.910, os] heat min faucns 33 ete " fos ante Joris 96] Seti 29] Seay reaen ” bos oss tone 9 2a tuyere 7 rafiscyenreadiee | fos [rote fran fons fae 6.0 alec anh dau, 1 Diethked re as 6 npane este oar Denonuinone 100) Meta See see Vow Nadu 16-7 sine i Paar 101] Dima for iro, rane ap 2 chee aces ve on 105] Mesto ae pony ryfaapimetytcua” fosr —|-rasas frame lose [ae [ors so [tse { 04] Fete ‘renene 30" “Derivative data piven inorder: perp esl, salven rom which enatlized : | “Derivative dia guaniaTABLE I. ORGANIC DERIVATIVES OF ALKENES, CYCLOALKENES, DIENES AND POLYENES 1) Liquids 1) (Listed in order of increasing b.p.)* (Continued) ~ 10) s4-Dinei fs 13995 [oor pestene 81] Cytoexene lov |-tonst fransss Josions [ar | r01-2" 1.759" | Meraptoscxnic | eid addut 1505 act 1190 q 15: 24:Dinio prenblleoy! Chloride, 78 hess, bp 16s s2]aapimetyiz. —fsa.4 [1277 rans fowsse lar — |e 1 sono seni] ss | sind taeaene 40 rar Joos ax Jaco. sos |.soen t4{2a dimes 826 [asa fiaoss lomo fae fra nso | s2as ksar fers fissio Jowsee fan [oase 13009 |i.sest 86] SMtempeteveee... 85.31 | 3900 Jow2 Ja fusre Jrasv0 fio 4 ar|smeastirana —fss0 1400 [or fae fas 14960 frsox7 ss aevetthesene [860 tse Joos Jae oor 1500 |1si10 6] zacdimeioia [865 0039 | 0.7006 tathstalene | sol esteinrtnrcre.. [toa -aanas freon Joos fa fos aos [sor 3 91 |sadimeat2. fer vio fons fae fos3-6 sos |i soo on|atMetmea (9737 tao foo fae fora" sie gal aMtetyivramae fore [126s Jiao2s fossrs Jar fou 2 sais fis 4] 22 Dimetslscon fet fas orn Male an, auc, ents : 3 is 95) 2cemscbmetnytte fs vaio ons la fos ssi 1.506 96.8 50s a e ee 96) SMethyis2scnene 1400 fo.200 a Y9-90" ayo Jsise on] sateagilane pi 25 fasio fosase flue Yor a sts | 566 gx] zvtenpittoene 920 |-torme ross foros Jae — |roas 1 simo fs ; ie Make anh addu. ee one 145-6, hepa: pose 1423,64 0.7299 Nirosochlorie Beroogunone a sn 196 7a 101] 2e¢-Dimetmt fos na frasiz forse 102] eDimetytevde- 3.2 4283 fore 1 tos] sMemtizana— foa.s ator [0.7099 04) Hepene bast |rioos |rsvr0 Josep Jae | 1062 14990 |15208 | Mercaptosssine To | Derivative dit piven inorder: mop, eryal color, solvent fom which epatalzed 15 eeTABLE TABLE II, ORGANIC DERIVATIVES OF ALKENES, CYCLOALKENES, DIENES AND POLYENES 4) Liquids 1 (Listed inorder of increasing b.p.)* (Continued) : _ | { a 1a foes 105] 3atemybveane pao | jie ford Jae [oso sow iso pci wre " st va [evan e vue] batty ps aos Jomo fa. ars wave fas sa to [ssmtens sas faiss fone ee caer wos|aatembitieee far fvass frame fore fa frso. a0 fine callers W>|ramcstenene™ boar [tases fiaoee foo fas floss isn fists Nat a Dime ae 10 |i eptene 5.75 Jros» Joo Ja fioss tsp10 |.sis3 renee 6s 17 ee Dimethsbaranck ti femmes. bo axe forse a ene outs) ee 112] :eimyea-gentene-.-- 6.01 ass for fa |r60 4" 15090 |isiz6 | leeetenies 113 2,8-Dimethyl-2- a5, 118.3 |iaz08 fo. a (97 isi a7 jheptane. ven } vay fete tisfiumttiepeee pros [tomas frets foro ar [soo som .si29 owe 113] Semin ba ase [oro 130 ft Nis owetepwe pas fae foros, fae foes tsa66 fisi30 sede 117 |atangetbeelo 00s aeons [ose ist stem neta te cane 1s [22 Dime fon sass Jaro Ja (oes fison passe 152 [Smet nio|emepadee joy a2 foros [as uae fo» 133 se trma te Uofteetiimanc. foray |9sae (ose foxse pene eae Tirtoe tai fstbimanias fois aico [a2 131 ioe ; Texadene henene oe hous aan foros Breas nxasne | ioe 23 as meth tev [02 ae for fae frome | css sone 136 siete )taelssoneenger fons fac fos oe ever ; 157 [Die 2h 125 ]Mtamiyatevee. 0278 |-11ss me fe [sos 1 oso 151 [Meant tis etalocehnce [040 a0 ~ i fatmante foe om | - tr ea 109 [2 meet vos [ceri jos haz ors se [ penrne 1eo| Sept see 13 |Site os | aos fozow 1 [2am ies 150m hove fot Naor [oso 62 [aime 24a 131 [Se Dimeytarne dts aos [oes | te [ei epee | heen | | 164 aetrineant3 horst |-1068 praia jorzte te eee 13 |s8e met. hos lass for ate one 161) ema nafezpmeigtacs poss [-isra [tame fore tes] saree sens | me | uss feztepnaine in foss 60 orm fsa fro sav frssose 16 [ima etn ; faiateros | rf tho tend tope : sera | 40" | rang pos 171] Samy asepe vohrapinamyiede- fos fsa frase forme | 2S imi Sen pares | 53 fsatamen 137 |4-Bthyleyelopentene .. [106 aso [o.798 | heptadiewe 13844 Dinage teen ioe pats fons fav fox Joo fsa ise 174] ei ey 133|Letntetopetere fos [ama lane [ote ee tao|ssimaimtad i009 rats [bates tee | Soave eivave da gneve ps A OT FONE om 16TABLE II. ORGANIC DERIVATIVES OF ALKENES, CYCLOALKENES, KENES, DIENES AND POLYENES 4 Liquids 1) (Listed in order increasing bp.)* (Continued) = ta feaeuae for ies = ve Mam sae bor pasos ue | rat letometnianese fora jar form fe fnss eee Is a | | #26 | ‘rieycle (2.2.10, | 151 |2.3.3-Trimethylt-— i083 | 68, Jiai7a— forssz | |. enter | 1 153 |1,5.5-Trimethyleyeto- [109° asm [o.7824 |. Reduces Tollen’s eve | 135mg fo late ore | ee bed mM 1156 |3-Euhyl-2-methy lt 10 ji.ais or |, on ISefeemieaonecee, foo iat” (lass Jostoe aes 3 | ic bicrainn sate 1 [stint eve fos eee |r| Wapeneeresecre bios | pane fos 'et paroeacne tanec patio [oa | Wes Soteamtarene Btls rarest efemesmae fe iain lots * pe ie 168 [3.44eTrimethyh2-— {11 14232 fo.7395 | Ws fe | cceesraacren ee ee | ee |e vs In sotcantepene 2 fio oars | eres * * ‘| snap oeagt zs jae fore | |TABLE II. ORGANIC DERIVATIVES OF ALKENES, CYCLOALKEN TABLE DIENES AND POLYENES 4) Liguids 1) (Listed in order of increasing b.p.)* (Continued) 75] 4 Metaieptee 2 fisio ori 0) nant ame Vlestemtasepene | [15 fits [nas fa sr Va] etgtaarne [ts fia [ns mt woe 119] 2uapropy-penene [its ats fos (apd 1a0| SAteastacteptene |: see 212] patty baie Ist fastemytaneten {i115 41 | fave ovis | Hal antoncee 182] 2matscearen [ie vate. oe aa catego [s/t | 2. tea] 2a dimaagtaa |e s eas 213] heDimettaran pee exe ussfentemiee jie ot zie] eee vse|semyraemetst 183 van10 ors | | 217) c-0cne ‘raPpete | | 3] hon hee tsr| cytepomfttsas [se frasso foszss far | emsabe Nivosoehine, Gubeen) | His.O%i = ayo] antes tepene | ime 105 220 amb Octee vss] eveeitee fesse fet frame [asus frre v1 texan v9 |sietyicis fus rae fons 221 o2-0cu0e pee 222] ean Nadine 191 | 13,$-Cyetoheptiriene [115.5 wa fis fy | | Maieic anh. advct. Ihevene eones) | 1082 50,60, 224] nebimattoea 192 | ase Dimeh-ntee [15 tas for | 193] Sowers taik [ora ‘si[eemee [he on tenene wepndre 224] avatenne vwsfzedimintia fica fxs frase Jorsi2 tenn | 221[ eneyt2anene. vwolanerimagit usa fuss fia for ao ener aaa] aaeDinet wi] debimigdee feos fms fran [ore sadene ‘Nae 229] sateen 199[ ata t2bepeae 7 ua foo ise 198] 2ecPropst-getn|17.7 Uaioe oso | 200] SMe atop (8 tai [oaas Big 2seae 201] 3-Dimeyiae: |i aus fasns ‘tbtskeannene wear TeDinetneete zor] 2Mtemsacpene fiisa2 [stax [ianiss forams see w5]2sdimamens fis ota isso [oer pa] ss dimen Nexen evatee } 24) aoc lio aisr lon Mercato 2 [Redan | ‘ci at Neaine | rors 2ie| stave 205|au-12.3-tametnyt 20." rast foro 35] 1233. Tewame ‘ocepentne ‘onto ttaurten) ‘Canpotee 206] Mes tpen 20.4 rains Josue inkcoeree 207|sauytasenmne [21 fia joss $y) 12 bimetnde- 20s [satemytepene ft aie Josas Nese | | Bo 2 | wieyelos2.n0ctas 1 "Desvatve data piven inorder mp. ctl color, solvent rom whieh eralized SDeiwaive da genineKENES, TABLE II, ORGANIC DERIVATIVES OF ALKENES, CYCLOALKENES, DIENES AND POLYENES 8) Liquids 1) (Listed in order of increasing b.p.)* (Continued) 310] meta. fiata™ fips fiausy forwer far far Tare frases | co) ai] racedetpaine [iiss |-t082 oso Hy-r et vite 212| sata 126 vain fora Bifeekodene fice fig sia fists fone Jara] wo iar” [ie 214} zanimaintatenne|i2ia [anni fraser Joss 35] haan |t2 thot ose fa fase isa] aie edie | aon fons | 213) cis-3-Octene [tp -126 | i4iz46 | 0.70808 an 218 nen gy [uta [atin bik out 215] atau ate 129s sane forsu Pies 0s of rmmcdame (iso [a7 |iana Jatin Merron ies aaifecaocene fraser fam frase ore 2] tamer fi rise fora see 2] 1stbimetstode fix vase Josue Nisan sian, ata vce | ee W002-5.0.CC1, 224] 1,S-Dimethyleycto- | 126 14s 0.3081 \Nitrosochloride, as[nedimaigts ans van nas|eNincaen [1295 Jan Joao Jae osm : oh “ a 2] eamniaatepae |is2 var [oss Mendon nf 29) Scart | 3 Wr sya ine moni 220 beydd.2a rene] 325 ater jn ws 32] heDmemigae. fis vase [oats 2a) dimadgiaae fis vaser fore 7 na{ stad, fis 40 vase forer Meapsesii bs[2simemgaa t3se.2uefiaes [Lane furviee ne i Os in pay. Worst +230] 3-Ethyleyetohexene 134 ast ox (Comptes 22] thitodevee [ie vas o ee 240] 37 ius |osar hile 241 | Bieyetol4,2,0 oct-2-ene |137-9 7 1410" [0.948 1»TABLE Il. ORGANIC DERIVATIVES OF ALKENES, CYCLOALKENES, TABLI DIENES AND POLYENES iqids 1) (Listed in order of increasing bp.)* (Continued) “e “ * Leone far ce] weve | of | OF iectaneon “ Noe | } ‘-Vimyleyclohexene BN ans s sassy fosous Nios, 255| contac "oct 244] 13Sycentne 244 2ataip tact. 130 vant foo 165] endine ste 0-40 tats foaess issue eee meh. i rms tout 266| een 7 ie] USS mettle [1393 sore] osu Nicoubiode nc Teeter | Yoo. Heenan fenton | Niowialita'® 260) emt sar) 2eDimeagi2a [139 43 pases |oran20 rales tote | aut | etme [95-05 see Jone fae [rw usar fis Irion, {28 |e etn rcs, 05 Visca, | 39|3ouee wo]isectimamide: fo vase oso | 270| he Cpcmete ae | "he te fea Noa bie sare fannie 2s1fropimtytise |i 221 tos Jo. 273] Gem an aan panoiaes ws | 1678 enn 274] ems 2 | (nine ‘ochre | adduct, 112-3, ter, enon 251) patentee. aves fore | ‘sauheee BalRebiagrice fata, [0 faitve [eae | 28] sf ecene 2.20% ade vas hy tte (Connie Soe ass) ieNomne fas 2 farsi eran 256] 1,3.S-Trimothyleyeloe [142,535 soz Nitrosochioride, 279) 246-Dienethyt-2,5- Ienene(Teteabo. 1B sro etaene hese Te 240| 21 Nome 29) snemtaace - fia s ann foun | 21] Aheeran | 258] Geter om i aie 2s] Fe ty net sie: Die ‘codohexane whoeoee i faspimsiae oti cute ri[sevinantaa — [at 14639" fozss 2 ine xe or anos foe fae fino vasa fata 25] 6mm a Be nse 2si| nas.timeiiote [ist 6 vase [oss 2) even | | = 7 i SDahae dane 20KENES, TABLE II, ORGANIC DERIVATIVES OF ALKENES, CYCLOALKENES, DIENES AND POLYENES 2) Liquids 1) (Listed in order of increasing b.p.)* (Continued) T wan Dams | ame | moni lw pee oF ~ nne e = | 0 [Sapene|wec| [er | os dime b9. 189" Nirosochtorie, 263] cise -Cyelooctadiene [145.1°% | 53 0754 |eetra 139 oe Niro 364) 1.8 Cente isoiss Jossni Wate ok add, a8 1445,A2N0, | 440015 6 ionchonde. 265) 44nimetyta.t- {148-6 vio |o.7s7 266] Cenehee (23.2.1 [1462 saves foas oi: 241 Nachle imethnbeyelo(22) | 68" oD aqme hepizene) Nios 1028 267] t-Timetdstexco- 146.2 Lasoo Naosschloie exe a Wee tase sou" | Nivea, 268] 1-Nonee. tsar [sia [raise af tansm rasa |i.a980 Vik Pet 369] Nowe. ian airy} 07394 | 30) sccyceactadene ish 9 tases [oan | | sromosccs Dorit 4 8 entane) rie no |aedimenyi25 [505-10 14699 cS 280}27-Noetiee. |iso6 [a2 |raase foraso 381] AlbledobexneQ- 151 Vase Josisce Ja) aia is en ‘Cyctohcrtpropee) create 22) bien 152-3 hasnis Josie nn ea posvenien aims 178 ‘en ibd more an 285] 4s.nimenyt26 [1529.38 sasns [oii poe 284 etydene sh vase [oan | ions methlesobexane.| Tiss ato poss Jiasisy Jorn ectaion "Derivative data piven in onder: pers color, solvent Irom which ellie aTABLE Il. ORGANIC DERIVATIVES OF ALKENES, CYCLOALKENES, Tal DIENES AND POLYENES 1) (Listed in order of increasing b.p.)* (Continued) n Toone | wets aaa T -m|sme [scoot [se aso Joos fa aor ne os 1 [rian ions eee eae feast Peto sm haa | aes ar Ta tei pa cea ane a So har fous ee fee fees pal eeoce ced te lasses |amoz vate — Eee 290, lists ji4s61— |o.88s. 31P | aTerpinene (1-13 arenes nian elem el bar ee ie foaoee ee ree fass-s ata fore fone Fg iia far ase fos * el oe a | walter aan hiss jae loss | a: +22 a | wemcaa' [0 ; isu es aed ashes i has lume [aes nea bc si Scoop | peels pees marae boven Toa me acm su) pata mohuscieamins fase Jeo ans rt seat come oar een i Sescucaeralee ao loa le +30; fees naan | tees | | meen a | ra 15} ste aa Sed” Yon foil oat nevene) | m»|siscee fro [eis fran ln uw fear fe Sn fa |e os ae eee sf twernae eau es ores wrens wi | etd foo empl sare nas su) Sey aon wo eran mn) eee ow lem |p) at: 400 ort a sal boreal trehyljctoheran) | | =F (cteoropeny3 303 | 6.8-0-Menthadiene (3 |170-1 1.4758 Joan | | methyleyclohexe: gtr saan Co | Peete mu seca lose ore ‘ceo | Tan Ce sg i oe oes ims un frau former far tus wre cel eee ea i | re ‘naan Bae Fra se ednae lus Toth ere 13| saps ier ! ts aca anon ca aesNES, TABLE Il. ORGANIC DERIVATIVES OF ALKENES, CYCLOALKENES, DIENES AND POLYENES 4a) Liquids 1) (Listed in order of increasing b.p.)* (Continued) T Bane] wee] Tomes cin pdr Nazosshorde, 207 [p-ntembene(ttso- —fir2-4 tases [osiow | Nitrovochorde 109: Hyde | ropridene- Wot bromide, mctyleelon | Nitosromi 08 | toprop 26 1216 Jose fre | 3 91-24: Ae cclohenadieas KMn0, pnonic 300 | ocMenthene(Ilso- 73: 160-2 1as7 Joss | | imethylylobexane). | 510 jmsMentene(Iso- 103-8 tae losais eopvicene-3 | aT acterpnese(iso- [738 ary foasns Ditydeochlride propytemetny [4st | 53-4, a1: Di- 2 Uheetohexadine) hydrobromise, | Se-9.me, Di yarotoide, 76, seal; Nios, 155, Matec anh, | asddt, 62:66-7 ats: +22 312 |2otp-Mtemasiene2- [174-6 tasise fossa Tuopeopyh ey | yc exadione Matec anh. adc. 313 |estsopopybe 7 Joss ia: 112.76, Sh Nap methyl ee ‘Nivosite, a 120-1: thoguinore enadine 8108-6 adic sid |1p-Mtethadine [195-6 vane [oss Indo: 49.1: ito Mato, 130 | tschopropyt2 ‘ea 110-8 rethyelseyslo- | 105. Maleicanh aig: +748 fenton), | sat 126-7. pt Nirosoclorie th ‘a oss area Joss rio Bs Dibyerochlonide, Fide, 106-7 Limonene 176-04 as fost fret 10 Nitrowchlorie 100-424 Die “ | pheoylsultery| horde, 95-6 517] ocarvestene(ss0- 176 7° pas08 |e 496 feta 17-8, me Dityrochlorie, ‘propery Pet al-chl 71 Svea, ‘Sjsloherene. alg: +973 s18| copropemite {176-8 are" |o.sie (is 68.2; Die |" metytyeone acne ‘ydeoshoride 72 319) Dipentene Inexo avon onan frie ras.en. | Dinyrochiorie ely: B06 Limonene) «7 50-L.a ineMenthadiene (179 hora es 4178 methylene) 121] Menogerene(S-ts0- [150-1 soos Jose fai us Inet, eco eran). saa) terpenes: {183 raves fossa facie 129-30 eB: +36 Nitro 2a |afraptorsscinie prepa bench eth Sochloide, 1 sidaddort {elohexadene) Nirosate, 116 mek 403] -24h0-Menthadicn 184 7 1.503 hee (hsopeopers 3 eyiyetobetene) 1 "Devan fa plven ort mp esa oor, solven from wish eralized BTABLE I. ORGANIC DERIVATIVES OF ALKENES, CYCLOALKENES, DIENES AND POLYENES 4) Liquids 1) (Listed in order of increasing b.p.)* (Continued) wef oe os | or ee se 221] Menage. fsae soe foxes eos 155, me. H Semmens | Sndleaaoce SP 2] Batg 525] Terpinolene 4Is0-|is6 tases joss [a 69 70 Matic anh auc, Ae bromine ‘ere ‘tis 18 3]isease Intivieyaeren) z x Coe | forme pin | 7 sas] tndere [sos ravas forse fae fas. 7 Mendes). mS | 7 sar|stadene tS aa oasis i Menace) ! rafting fone Loe foam Jonson Jan {re ane fran Bee s29|encycloeeme 988 sass Joao | m1 0, Seba sod 13] Easiea lowe bee [ow [mm bow b- | ies slew a | 1 18) Meme 16) Pane 31 | etc bot: |-2s07 juanse forss ue + ie araftetamdecene pst fans fraser fori fa 0 Mercaniosssinc m9" odbc é 233) cate per psooim Josisns astfaemadeete.... pki [os franwe former [ae Joos vasor_ |iaass ig gs] tenders fase frame form [ae {2257 frs.at eae ec 080-8 an] EM ists ness fae |r 6 acne : nie] rOgmiecwe oo buaiefixe fis Joris fas 2a | "Derivative dita ven order ip sctyatal olor solvent from which eyedrch: Malic as 205 8 enh a Sbace w s tonne adda oe ot KMa0, = erases, Merete initia a 1030-8 TABLE I ORGANIC DERIVATIVES DIENE OF ALKENES, CYCLOALKENE AND POLYENES 42) Liquids 2)(B.p. at reduced pressure only. Listed alphabetically) 1 Bicyll1222octadeca 14.16,16erene Biyco(4.2.0 octane Buryeycloetaterrene. rons-Cydodecene 159413-Cyclobexade ron Cyelononene 1xCydooctadeadion 13.Cyelootadene 12 |26-Dimehyt2Soctadiene 13 |Eeyteyetooctatetrane 14] SMethseyctohepene 15 | Metileyeloctatetrnene 16 |7Pentaecene 15 | Propyeslootaetraene mame | Macaca Wasa S200 Maleicanhaddut, 13-4 ar vane uo soa3e fo wie> 68-70" 1422 oss {0,+sebscecaci, 134s 93-50" saa pra 14799. Joxsrs | Phenlazdewdduct 978-42 ns: 14899. Jostia jax | s340 255) 1 ab40e foscon jos =0210 -54 loso4o 106, i492 0.4725) Nitrosochlorde, 109-10: Nitrate, 2108, 107 1.3219 foxgso»| Matetoanh adduct, 18.555, be-igr: AgNO, ss0-5" 1.4500 fo.ass 8 15187 Jo.s996°| Mate unb. adduct, 97-45, bs aplobexane [AENO,adct, 136-558. e970" 12016 oe ease lo sore aan [ors 15131 Jossro Derivative data given in order: mp, ental color solvent from which eralized 28TABLE Il. ORGANIC DERIVATIVES OF ALKENES, CYCLOALKENES, DIENES AND POLYENES b) Solids (Listed in order of increasing m.p.)* u jars [ioxo, fraaas [arene 13838" | 2x6 [sana [rae] areson| | he [ima fasom>}asze0 Phenylaide adduct, Methylenes.7.4.9svahydroindene) is 4 tenioeene ana [sss [asset fazer? s| sr 140s | sa02" 6 las [3 | Lasie® fosoas® 7] '453f390 | asz7* fosoas® s| 87 aor {1st fosnos* 9] crete 295-50 ARNO, adduct 2004 10|41.Camphene 22 Dimer 0 [59-00 Jac ona Yass methyerebiylo2.2bepene) 11) sCamptene s.3 fase 24 Dinitropens- ; sulfeylconge, 121-2 Hydeoetlo- fide, 25-7 12] tHtepacoene saz fae 13] teiacmtne laos aus 14] Meniacentene eis fast fas? |s05 jes fans ros {an 23 |as9 n39 | 96 755 |s03 a7 dso ree |si2 mae |s03 24| Biya 2.2.2-o0t2-ne nine [ose Beane] 2) 50-5 es “Derivative data given ona mp ery colo, solvent om which enstlzed s uperooked gid a 20" 26 Hgsalt Fr hydrox fo 48,469 Hydra Deiat WARNNO adduct. 2338 Dinirophen es ctor, 12 Hycocho fe 1257 EXPLANATIONS AND REFERENCES TO TABLE III 1H salt (Mercurie acetylide,* 2RC= H+ Kalle + 2KOH + (RC=O:Hg + $KI 4 21,0 Mercuriesal From the terminal alkyne and K2Hely (prepared from mercuric chloride, potassium iodide and potassium hydroxide) For directions and examples see: Linstead, p. 52: J. R. Johnson and W. L, MeEwen, J. Amer. Chem. Soe 48.469 926), Hydration to form carbonyl compound Terminalaceiyenes: RC=CH + H0 84. RCocH; HiSO4 Metis kone Other acetyleass: RC=CR’ + H;0 “B24, RCOCHR’ + RCH;COR’ oe Mixture of ketones From the alkyne in methanol and a catalyst composed of boron trifluoride etherate, red mercuric oxide and ichloroacetie acid For directions and examples see: J. G. Sharetkin and E. M. Boghosian, Anal. Chem,33, 640 (1961), From the alkyne, mercuric sulfate and sulfuric acid in 70% methanol, in 70% acetone or in 60", acetic ai See: Cheronis, p. 576; H. Erdmann and F, Kother, Z. Anorg. Chem. 18, 48 (1898); R. J. Thomas, K. N. Campbell and G. F. Hennion, J. Amer. Chem, Soc. 60,718 (1938). From the alkyne, mercuric oxide and sulfuric acid in alcohol. See: J, R. Johnson, A.M, Schwartz and T. L, Jacobs, J. Amer. Chem, Soc, 60, 1882 (1938), NOTE: For directions and examples for the preparation of the semicarbazones and the 24-dinitophenyl- hydrazones of the formed carbonyl compounds sce explanations and references to Table IX and X, p. 141, 142 1, Derivatives recommended fr frst ria, WARNING" Thien aninstroction manual. References shoud be consulted forthe preparation of derivatives nTABLE III. ORGANIC DERIVATIVES OF ALKYNES (ACETYLENES) ' 2 Liquids sted in vd af inetasing bp. No, None towing | cies) ae | oor 24D | an | Meson | Maceanour Ne Ne aoe | ane) ee eat i ee Mis | 1 | Ethyne (Acetylene). 84.0 808, 0.6179" (Acetatde- (20.2) ]¢168) (162-3) 123 |44-Dimethy sat ‘sub. hyde) cee a arwrecncan [SE Vas |... fesiesfacuowe [a fue foe 2st pe mse ame sfemempronnse [ress [ass (1am Jomo Teele Csopropsacttene) bp.23 1, % | StHexad 6 | 2-Butyne (Dimeshy! 2726 | =32.26 [1.3921 |0.6901 |2-Butunone |82 6-7 135-6 | Vetrabromo deriv... (Diving! acetylene) 43, eth.; 24-Di- 1 21 | Hexen nitrophenyl- ' a, peers fet eae enone se eeremnan oes soem ses [aaa | sraefoasm : pos so [caca [ctr ious |atoss rats fas zemronefions [us |rsesfies fanned so Se | os eS Seminar 1 fentremmoe — fons fan ls slams eee Stina ce at | 13 |2-Pentyne (Ethyl methyl | $607 —109.3 [1.4039 [0.7107 |2-Pentanone |102,3 | 145 112; 106 IKMn0, -= formic a es | cafes reece ee i J-Pentanone | 102 156 138-9 (39) 2-Heptyees safreetessneesi [92-401]. frat [ars \ a 15 | 4-Methyt-t-peatyne 105.1 | 1.3936, | 0.7092" 1000-5 i 40) 2.2,8,8-Tet eta. 8 2 RS te aes 1) 17 | A-Hlexyne (Bury! ma = 1319 | 1.3989 0.7158 |2-Heranone | 128 to67 fis fe.2 4 al acetylene} snectylene] 18 | 42Methyl-2-pentye 720-5 | 11037 | 1.078% | ort “ ies acetylene) s eens 20] 1,3-Pentadiyne 750-8: |-45t0 | 1443 | 0.7375" 45 |2-Octyne (t eles me * 5Hl TABLE III. ORGANIC DERIVATIVES OF ALKYNES (ACETYLENES) ‘a) Liquids (Listed in order of increasing b.p.)* (Continued) aneanEanE Thanionprog ROMER > ROOD Mivataees Na ae pane fume | oe | BF neo Tian Micdaeous aoe }p.ce | sent pana . ine Pane 1B feacDimemytzpane [2.9 30 aon Joris (erst mets i ‘nen aelatteyac(Migt [93.7 40-92 717 [aatsanone (roe foe? [2s ropes) a ritecmone (12s fis ju 25 ttexeasgne etal fas oss 1 2-Divomo ser Vins) nears comer SSSI op arab deriv 140 sow ae t, 2|tstinadinrsne [aso [arzar [isms Jornsr ae (Diving acl. acca ran 2 |Etteen-tgne a oe 1 2-Divomo srs opts ‘ boaso se ler ere, tr ee bromo tas so" 28 einyigenne,,...]a7.0-85 taioa_| 07246 Je [isnexadeetDi [srs | Wa3ee [Lanai fo roses a) a a 10 ttesentgne se'9 sasis forma Jaman Jrss- |os-os eons | 68" bp. 795-805) 4 21 |2tethyttenyne. 952 sana ee 43] tMedytategee, [984 Vara [otakss deny 132 6 ; 23 [seme pemtentyne|96s sana | reno» Si]sMetytcbnepene ) 95 10 ‘tion 1360 an Sleatenaccrenst fons | soe’ taper foes | tepanon] sid foo” fish iar fei rare sacoien) ‘i cae 26 |SMtabgr2teagne | 126 ox Pes 3 |sAteatceoongne | (085 oa oes 28 bacon bt props | 105 0737 |aieptinone aa a5 [ide we + bopoee. aecene) pron 29] 2eHepayme (Bury! is.25 4290 [0.748 | 2-Heptamone|151.2 | 89 123,127) { imenyt aye) * 3-Heptanne ak c aolrasstanmanst frie [ive | aoss fo7i0 - \ here (Der bt dost) 41 |e rom |-ss_ frase Joist 2]vocgmietiegt fise2” [oma tae oer |2canome fini fesse fides fo’ 9 scene) eal 3] eOcyee Dine fn04- sane Jose secre a1fsocgec tania” | aio. vans ors vse ee) : 45|2Oaye Heimat | 80-4 tas fore [2osamore ]irs[orsos fises i em) a ' soammore fio fers fire. 1.4-Dinitrophenyl- wee ene ee Asleromsey-buys iso e+ raasee Jor enonione iar s sr 8 rs os Propel scesene) Neen lone . {Dessative da given order mp esta olor, sovent rom whih eyatalion 29 oo OeTABLE III, ORGANIC DERIVATIVES OF ALKYNES (ACETYLENES) 4) Liquids (Listed in order of increasing b.p.)* (Continued) ison | so 48] Nong Meth pent 153 | ytoctyne is7s 50|2.Noeyne Mets nest | 161 aceite) 51 | Je Nonatiane 169,550} 2728 selrpeeynernoeyt [1750 | 4 2] sDeeymityibes! [17S 6 sa] seeynecdibuyt | 77-1008 | 73 settee) 35 |cyeanonee wae [6a si |27-Ne wo [aso 57) tadecne(ticnde: | 195; 25 tyne Nowylacevlene). | 96.3! 8 | cyeadevee 203.4" 763" 59] Dodane Dipenyt | 209": 90" asetlee) acetylene) 00" 61 ]1-teeyne Unde | 24 s scetlene 29s 2] tctetradeeyne Dede! |252, Jo selene gai" 63] ePemtadeeyne (Tess! | 265, | 10 sssene 7 cot] itexadceyne(Teras | 288; 105 decyl acetone) 181 L490 Lae 1890 ery Lan Lata 07616 0709 Osis a.m6s¢ oss on sie" oa 0.3965 Bade Cyatoe 2.Nonamone | 195. 2-Decanone [2155 bscunone |206-7 SDecinore pea 100 1220-5] ” NaH at 210" ebucic ack, M.S esse bp. 218 "Derivative da pvea wonder aps ayaal olor, solvent from which enstalized 30 1] btepadesne 2] 2e-Oeadiee 3] Hosadeyae 5] UNenadeeye 7] aedcnyne 8] tenoyee 10] tres, 1 tTeracosane 12] -Peatacoee 13] EHexteosye 14] tetany 15| Loctacoae 22) 1Penaiee 35] aenaiac 24) tet 25} Loctatico 26| 1-Nonatinen 27] -taracone Dervaivedatagn = supercooledDrone» ‘ehac ad, 1,5 Dodeyne. bp 215 TABLE IIL, ORGANIC DERIVATIVE: ’) Solids (Listed in order of increasing m. OF ALKYNES (ACETYL! NES) 1] epsdcoe. a» | cae [oroer 2 dctaine aa | tsa | Osage Octadeeye ni | tae | osoas 180 4] 2oaadeeyne wo | ise sos 5] ieNenadecr. sy fae [aka | c0sot sans 7 6| tricone. as | uo | vaso? | sont as faa | case | oar? so | as] vaste? | ostast ss | vs | tesa® | Ostet sv | ats | ase | oar! w | as Lasos | osivo’ | 15] LOctaconae ofa | asst | ost | 16) ENomcen os [a2 pias | ane | 10] Seteiaconae & | 4a one 14] Leconte. & |i ost 19] 1etaconye fase | rast | eat 20) Actetiaconya. a | aes | tase | ost 7 sa [ane | Vest | ozeot | | tans | onze 23) Lexicon se | sore | aaarst jm | a | aeast | saat sos} Lasast_ | osiost si] taaa* | oxioit Derivative data given wonder np .er So supercooled liguidat 29 al oor, oven rom which erywalized 31EXPLANATIONS AND REFERENCES TO TABLE IV Muro dervaive* ArH} HNO; + ArNO, + 1,0 eernative From the aromatic hydrocarbon with concentrated nitric and sulfuric acids, For directions and examples see: Cheronis, p. 578-80; Linstead, p. 48, 49; Shriner, p. 249: Vogel, p. 520; Wild. p. 24. From the aromatic hydrocarbon with fuming and concentrated nits acids See: Shriner, 249; Wild, p.24 From the aromatic hydrocarbon with fuming nitric aid in acetic acid. ‘See: Vogel, p. 520. From the aromatic hydrocarbon with nitric and sulfuric acids in chloroform, ‘See: Vogel. p.$40, Acetamido and Benzamido devivatves.* fAECOnO. AeNHCOCH, + CH:COOH 5m) HC Aceamido ano, HCL anny ‘eivave cottscor an ESOS AINHCOCgHs + HCL Beneamido ‘deivatve Nitration of the aromatic hydrocarbon is followed by reduction with tin and hydrochloric acid. The re- sulting amine is acetylated with acetic anhydride or benzoylated with benzoyl chloride. For directions and examples see: Cheronis, p. S81; V.L. Ipatie and L. A. Schmerling, J. Amer. Chem. ‘Soe, 8, 1056 (1937); 60,1876 (1938); 68, 2470 (1943), o-Aroylbenzoic acid product with phthalic anhydride OC = OE : oo o-Aeoylbensic acid From the aromatic hydrocarbon, phthalic anhydride and aluminum chloride in carbon disulfide For directions and examples see: Cheronis, p. $48; Shriner, p. 280; Vogel, p. $19; Wil, p. 28: H. W. Un derwood und W. L. Walsh, J. Amer. Chen. Soe, $7,940 (1933). From the wromatie hydrocarbon, phthalic anhydride ang aluminum chloride without solvent. ‘See: G.F. Lewenz and K. T. Serijan, J. Amer. Chem. Soc..78, 487 (1953). 24-Dinitrobenzenesulfens chloride derivative Aryl 24-dinitrophenst sulfide} No: (03 ide in 1,2dichlo~ For directions and explanations see: Cheronis, p. $85;C.M. Buess and N. Kharasch, J. Amer. Chem. Soe, 72,3529 (1980), Penne Nos Nos Ad + OWN on ~ ant-ow—~ on Nos rome NOs (Moteclarcomples) "Derivatives commended for fst ah WARNING: This aotaninsrution anus, References should he consul fr the preparation of vats 2 Sip 13s 24 Oe Stes Aci Wal. 320, v. Un. m Soe. EXPLANATIONS AND REFERENCES TO TABLE IV (Continued) From the aromatic hydrocarbon and pictc acid in alcohol. For directions and esamples se: Linstead, p. 50; Vogel, p. S18; Wild, pp. 29-30. From excess of liquid aromatic hydrocartion and prec acid without solvent, See: Wild, pp. 28 9; Baril and Hauber.J. Amer. Chem, Sov. 83, 1087 (1931), From the aromatic hydrocarbon in methanol or in dey benzene ‘See: Cheronis, pp. 5K2-3 oH Noy on No, Swyphnic acid Suyphoate (Moteularcompley) rom the aromatic hydrocarbon and styphnic acid (24 6-trintroresoreinol) in acetic acid For directions and examples see: Vogel. p. 519; W. J. Hickinbotiom, Reactions of Organic Compounds, 2nd ed, Longmans, Green and Co., London, 1948, p. 76 1.35-Trinitrobenzene derarive From the aromatic hydrocarbon and 1,3,S-trinitrobenzene in alcohol, acetic acid, or benzene. For directions and examples see: Vogel, p. 519. 24,7-Trntroftuorenone (TNF derivatve.* No» Nor 4 An + ] Am. UI ow NO: on No» INF 2.42-rinicooreone molar omni From the aromatic hydrocarbon and 2,47 For direcrion/and examples see: Cheronis, pp. 882-3: M.Orchin, J. Amer. Chem. Soe. 68, 1727 (1946): M. Orehin, L. Reggel and E, O, Woolfolk, J. Amer. Chem, Soc, 8, 1223 (1947) From the aromatic hydrocarbon and 24,)-tsinitrlluorenone in glacial acetic acid ‘See: M.C. Kloetzel and H. E. Mertel, J. Amer. Chem. Soc., 7, 4786 (1950); M. D. Soffer and R.A. Stewart, J. Amer. Chem. Soe..74, $61 1982) From the aromatic hydrocarbon and 24,7-teinitrofluorenone without solvent See: D. E. Laskowski and W. C. MeCrone, Anal. Chem, 30,542 (1958), Acids from side-chain oxidation initroluorenone in methanol-benzene and ethenol-benzene AR ArCOOH tomatic ‘sid “Derivative recommended fo WARNING: Thies fraction marl, Reference shoul consulted for he preparation af dersatses 3BEXPLANATIONS AND REFERENCES TO TABLE IV (Continued) From the alkylsubstituted aromatic hydrocarbon with potassium permanganate in sodium hydroxide or sodium carbonate solution, For directions and examples see: Cheeonis, p. 585, 627; Linstead, p. 50; Shrines, p. 280; Vogel, p. $20: Wind, p26 From the alkyl-substituted aromatic hydrocarbon with sodium bichromate and sulfuric acid ‘See: Cheronis, p. 621: Shrine, p. 250: Wild, p26, Suljomaide.® + clsosH = arso;cr —“ arsonty Sulfonyt Salfonumide ore rom the aromatic hydrocarbon and chlorosulfonic acid in chloroform, followed by aqueous ammonia For direcions and examples see: Linstead, p. 49; Wild, p. 27; E. H, Huntress and F. H, Carten, J. Amer (Chem. Soc. 62, 51 (1940); EH, Huntress and J. 8. Avtenrieth J. Amer. Chem, Soe, 63, 346 (194). From the aromatic hydrocarbon with chlorosulfonic acid without solvent, followed by ammonolysis with dry ammonium carbonate See: Wid, p. 27 “Derivatives recommended fr fit i WARNING. This notansnaructin mandal References should he consuls forthe preparition of eivatives 34 ee Oe 1 [ences Ethene Xen | ra.xstem 6 fia-xpteae opropyt 8 Jr-Propyt Gta 10 efit (tinh ‘sro | (o-Fihyh 13 feeroaye afagaa (edo 15 | batt “Dervatveds0 with TABLE IV. ORGANIC DERIVATIVES OF AROMATIC HYDROCARBONS, ) Liquids. (Listed in order of increasing b.p.)* 7 ew for? [ss [ison fosrwoi] a aa tH |ia0 [oaononie 6 i nas mia see tios }-9s }aveia}ossas) a2 pita tolzaa: fist fis Jovi bernie ™ ey i Slo. x time 137 3] rmsennne v2 fon ]1.9554/055600/o60. acim foaa [rez for fons =beie ee | ot 2 Salon- i mie, 109 4frsexvene ra fisa6_ | 4950 foseis|oo 23. 1a, fines fous ster ry tas th sa P00 Seton 167 sande vo0 [eras ama fossa] au 16 Jona. = nonbhie it ie sai Selon 37 haxvine vasa | 25:8] 034 sso sw asa 8 losis pie ite 208 Sarai. 14 2 preps Came) 9601 | vapizefosir9 pain: fsmono: }138 loud. = bmn i |e Salon ae mie. 10 he & | etropinezee 1592 | v9.59 | ame oscone| ios aaa somone: fi lois beni te |e Ve | the son a] mstamedstenem — 1613 | sass | rans fossss lows, -isophtaic imtineacne) od aah vo} ematameytemeae |1624 | 6225] 4350 fois ous ere ‘nisin bens 0, uifrasriimastenne — [1647 | 4472] 407] onesie or pad By oxides ints) ‘ 3 Sati be oii tt 12] emstamaiytenene [1652 | 2093 1304560099 xs pai tino) 2068 i bacerenes von |-s498} 1.9056 5650 ata: [mone 10.1 [Osa hei [te 36.1 See | dae ina | 210 a-rimentenrene — | 69 | -sio1 sous} oss] 9 en ovis. inti aesecmen), iss vats 39d 15 | saben rma |-sts3 | vatet| ossi2r sooo} = bn vi ma |-7557} Lazo] o soar ata: simone: 1.9. owe, ~ bene Bn De tere | dent oe vist |-615] 14030 | 08610 SBervave data phon order mp. crywal olor, sven! from which eytallized 38TABLE IV. ORGANIC DERIVATIVES OF AROMATIC HYDROCARBONS iquids. (Listed in order of increasing b, .)* (Continued) % ine site| as | or rome Rate ate Param | ston ~ 1e]ta.ctimeanienmne [iron [254i [isis oases] ws fot = pent 1 ernie iemimctitee) teas 0 Fa 19] onc Popertense | 6s 1st oe as9 «2 feats 20 fidane wn tsa [ovess 2] vnayta 21 theprpsictmcibene [714 | 6094 amy fo¥syy Sea iS 7.5 ‘eRoprottoee se Sem ahs ime 4 een 22 faerppttmatitiernee [17835 |-7121 [som fostes be, Terbromo er Bo (Chorale “os 00s asf Scans 4 [suomi 23 ji sDiyteaee tia vaya osoas aun na Metyisqroptionne {1518 sans fossio , entropies) 47/12 ime 2s tno vas [2 |istes fons onset ssi payer 26 emoeaee Twa |is Lasoo [oseors sna for fs 4 feo : fs Coe Me «9 not a oe 23) atatytorpstearne | 1819 vas [oss 30 eaten Poster) 5i fia bem 28] 1.0saheneoe 4 1 sexs] oso enone 23] taintytemene tox taba fosroe <2 Pmt 5o]t3cbimeantSctberee [this Jaa [amet [soe Sain i bom, 5; etna inne “orbs ¥8 si facie safratadsiagrptennne [inex ]-so2 [ramen [oars ace ‘etomiien) 55 pine 22] 23.Dime perpen | 16 vaso |oase (oetuy ‘Neopet ss ise 33] tabi aes | 69 108 [oss Ass surname. 107 ‘emene re st fis a 5s oe || 2eyindae ‘wo sero fososs 38] 3 Maylene 1 tase [oor cami ds urs s9}12aste ‘oduren 60 stent 36 atatsndne 18890 usa foo eat wih ‘ver 50.350 + Nap thle 03 s7}13.0imaytaiienmne. ise |-«.0 fis0ie Joss seu r= 250:te 6 13-bim ins tromesse 2 ames 30 6213 18] setunyttemetiyterene 19: | 419 fr as4e [osos7 ‘eae ‘Sen puters) os fein 29[12imcastemsbenne [18058 [ort Jrsoat fosras lois acd 554 10 | 1. Dima. 0 us oao04 id hemi Teac. 0 78 | Derive das ven ner pS nn net om wah SAT | x6 i a oe