CRC HANDBOOK of tables for ORGANIC COMPOUND IDENTIFICATION Third Edition Compiled by ZVI RAPPOPORT, Ph.D. Hebrew University of Jerusalem, Israel CRC Press, Inc. Boca Raton, Florida Copyright 1967 by CRC Press, Inc. This book represents information obtained from authentic and highly regarded sources. Reprinted material is quoted with permission, and sources are indicated. A wide variety of references are listed. Every reasonable effort has been made to give reliable data and information, but the author and the publisher cannot assume responsibility for the validity of all materials or for the consequences of their use. Neither this book nor any part may be reproduced or transmitted in any form or by any means, electronic or mechanical, including photocopying, microfilming, and recording, or by any information storage and retrieval system, without permission in writing from the publisher. Direct all inquiries to CRC Press, Inc., 2000 Corporate Blvd., N. W., Boca Raton, Florida, 33431 @ 1967 by CRC Press, Inc. Formerly The Chemical Rubber Company International Standard Book Number (ISBN) 0-8493-0303-6 Former International Standard Book Number (ISBN) 0-87819-303-0 Library of Congress Card Number 63-19660 Printed in the United States 15 16 17 18 19 20 Printed on acid-free paper Copyright 1967 by CRC Press, Inc. 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 @ 1960 by SCIENCE 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 64 by THE CHEMICAL RUBBER CO. Third Edition Handbook of Tables for Organic Compound Identification Compiled by Zvi Rappoport, Ph.D. Copyright 1967 by CRC Press, Inc. 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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 D., Rice University, Houston. IMMUNOASSAYS FOR DRUGS SUBJECT TO ABUSE Edited by S. J. Muld, Ph.D., New York State Narcotic Addiction Control Commission, et al. MASS SPECTROSCOPY OF PESTICIDES AND POLLUTANTS By Stephen Safe, B.Sc., M.Sc., DJhfl., and Otto Hutzinger, Ing.Chem., M.Sc., Ph.D., National Research Council of Canada. MERCURY IN THE ENVIRONMENT By Lars T. Friberg, M.D., National Institute of Public Health (Stockholm), and Jaroslav J. Vostal, M.D., Ph.D., University of Rochester. ORGANOPHOSPHORUS PESTICIDES: ORGANIC AND BIOLOGICAL CHEMISTRY By Morifusa Eto, Ph.D., Kyushu University, Japan. RECENT DEVELOPMENTS IN SEPARATION SCIENCE Edited by Norman N. Li, Sc.D., Exxun Research and Engineering Co. TRACE ELEMENT MEASUREMENTS AT THE COAL-FIRED STEAM PLANT By W. S. Lyon, Jr. B.S., M.S., Oak Ridge National Laboratory. CRC CRITICAL REVIEWS~~ IN ANALYTICAL CHEMISTRY Edited by Bruce H. Campbell, Ph.D., J. T. Baker Chemical Co. CRC CRITICAL REVIEWS~~ IN TOXICOLOGY Edited by Leon Golberg, M.D., B.Chu., D.Sc., DiPhil., F.R.CiPath., Chemical Industry Institute of Toxicology Direct inquiries to CRC Press, Inc. Copyright 1967 by CRC Press, Inc. PREFACE 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.e., 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 I.R., Far I.R. 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 their 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. I. 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, 1958. 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 earlier 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 Mrs. F. Thomas in the publication of the book is gratefully acknowledged. z. R. Jerusalem January 196 7 Copyright 1967 by CRC Press, Inc. Contents Abbreviations Explanations and References to the Tables Alkanes and Cycloalkanes Gases, Liquids, Solids Alkenes, Cycloalkenes, Dienes and Polyenes Liquids, Solids Alkynes (Acetylenes) Liquids, Solids Aromatic Hydrocarbons Liquids, Solids Halides A) Alkyl and cycloalkyl halides 1. Chlorides, Liquids and Solids 2. Bromides, Liquids and Solids 3 Iodides. Liquids and Solids B) Dihalides and polyhdhdes (non-aromatic) 1 Fluondes 2 Chlorides, Liquids and Solids 3. Bromides, Liquids and Solids 4. Iodides, Liquids and Solids C) Aryl halides 1. Fluorides, Liquids 2. Chlorides, Liquids and Solids 3 Bromides, Liquids and Solids 4. Iodides, Liquids and Solids Aicohols Liquids, Solids Phenols Liquids, Solids Ethers Liquids, Solids Aldehydes Liquids, Solids Ketones Quinones Carboxylic Acids Liquids, Solids AcyI Halides Acid Fluondes AcyI Bromides, Liquids, Solids AcyI Chlorides, Liquids. Solids Acyl Iodides, Liquids, Solids Acid Anhydrides Liquids, Solids Amides and Imides Liquids, Solids Esters Liquids, Solids Copyright 1967 by CRC Press, Inc. Contents (Continued) Ammo Acids Amines Primary and Secondary Amines Tertiary Amines Liquids, Solids Carbohydrates Liquids, Solids Nitro Compounds Liquids. Solids Nitriles Liquids, Solids Sulfonic Acids Sulfonyl Chlorides Sulfonamides and Sulfonanilides Thiols (Mercaptans) Thioethers (Sulfides) Acid Dissociation Constants of Organic Acids in Aqueous Solution Acid Dissociation Constants of Phenols in Aqueous Solution Dissociation Constants of Organic Bases in Aqueous Solution 1.R Infra-red Correlations Charts Far 1.R 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 Diamagnetic 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 Copyright 1967 by CRC Press, Inc. LIST OF ABBREVIATIONS USED MD a abs abt ac a ac anh acet add al alk amor anh arom aqu asym , as blk boil bp.B P br bz brt brnsh Q CQ caust chl cl -bz col comp cone cor cr , cryst d d,D dcnv dehq dil dist dk dl , d,l, D, efflor et et ac eth exp f i fl fluores fp frz specific rotation acid j absolute about acetic acid acetic anhydride acetone addition alcohol alkali amorphous anhydrous aromatic aqueous asymmetric blue black boiling boiling point brown benzene bright brownish cold about caustic chloroform chlorobenzene colorless compound concentrated corrected crystals decomposes dextrorotatory (or D-configuration) derivative deliquescent dilute distillate dark L racemic efflorescent ethyl ethyl acetate ether explodes from flakes fluorescent freezing point freezes um ;Iac 'lit ?lyc gran grn , htng hyd hyg , hygr ; i ign msol 1 ,L leaf. If lg 'gr hq Ing It Ivs /Ti- me , meth micr mixt ml mod monohyd monocl m p , M P need , nd 0- ol or ord org orth oxid P- pa part pet pet eth ph ph hydraz PhNO 2 pl powd fuming glacial glittering glycerol granular green hot heating hydrate or hydrolyses hygroscopic inactive insoluble ignites insoluble levorotatory (or L-configura- tion) leaflets large ligroin liquid long light leaves mcts methyl microscopic mixture milliliter modification monohydrate monochnic melting point needles ortho olive orange ordinary organic orthorhombic oxidation para pale partly petroleum petroleum ether phenyl phenyl hydrazine nitrobenzene plates powder pr purp pyr rac reel recr redsh rhomb r rh s sec scar s h sh si sld slend sm soft sol , soln solv st stab subl sym tab , tabl ten tetr tol trans thk tncl trim uns unst vac V var vic- V1SC volat vlt w wh yel yelsh, ylsh > < oo xyl prisms purple pyndine racemic (or racemate) rectangular recrystallization reddish rhombic rapid rapid heating soluble secondary scarcely slow heating short slightly solid slender fm oil small softens solution(s) solvent(s) steel stable sublimes symmetrical tablet(s), tables tertiary tetragonal toluene transparent thick tnchmc tnmenc unsymmetrical unstable vacuum, in vacuo very variable vicinal viscous volatile or volatilizes violet water white yellow yellowish above, greater than below, smaller than irascible xylene Copyright 1967 by CRC Press, Inc. EXPLANATIONS AND REFERENCES TO THE TABLES The following section gives explanations and references for the preparation of the derivatives appear- ing in the Tables Formulas of the derivatives as well as the mam 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 reagents available to him in his labora- tory for the denvatization 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 usually given for 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 are given, assuming that at least one of them, or another equivalent publication, would be available to the worker These are N D Cheroms, J B Entnkin and E M Hodnett, Semimicro Qualitative Organic Analysis, 3rd edition, Interscience, New York, 1965, quoted in the text as "Cheroms " R P Linstead and B C L Weedon, A Guide to Qualitative Organic Chemical Analysis, Butterworth Scien- tific Publication, London, 1956, quoted in the text as "Linstead " R L Shnner, R C Fuson and D Y Curtin, The Systematic Identification of Organic Compounds, 4th edition, John Wiley and Sons, New York, 1956, quoted in the text as "Shnner " A I Vogel, A Textbook of Practical Organic Chemistry, 3rd edition, Longmans, Green and Co , London, 1957, quoted in the text as "Vogel " F Wild, Characterization of Organic Compounds, 2nd edition, Cambridge University Press, Cambridge, 1958, quoted in the text as "Wild " In addition, leading references from the original literature are also given Although the literature cover- age is not complete (especially for the common derivatives) it was attempted to describe different methods, and to give as many references as possible to less common derivatives having limited scope More references can be found in the 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 different derivatives are arranged usually in the same order as in the Tables Occasionally, this order is changed in the explanatory notes in order to describe the derivatives in a logical order (eg, in Table 17 the phenylurethane appears in a separate column, while the phenylhydantom appears in the "miscellaneous" section in the "ex- planations and references" section the phenylhydantom appears directly after the phenylurethane) Derivatives which are followed by an asterisk are those recommended for first trial Other derivatives should be tried after these Although "Ar" usually stands for monovalent aromatic group, we used it a few times in the following sec- tions as a polyvalent aromatic residue This was done only for demonstration purposes Copyright 1967 by CRC Press, Inc. [...]... (Isolaurolene) 24-Dimethyl-CIS-3hexene 3.3-Dimethyl-2-ethyl1-butene 3-Ethyl-2-methyl-lpentene $3-Dimethyl-2-hexene I-Methylcyclohexene Bromine addition product Melting point Miscellaneous O C 07 2-EthyM-methyl-lpentene 3-Ethyl-I-hexene 2.3-Dimethyl-I-hexene 2.4-Dimethyl-2-hexene 3-Methyl-I-heptene 2.4-Dimethyl-I-hexene 2.5-Dimethyl-I-hexene 3-Ethyl-3-methyl-lpentene 3.4-Dimethyl-I-hexene 3,4,4-Trimethyl-2pentene... 5-Methvl-irans-2hexene 2-Methyl-3-hexene 2.4-Dimethyl-2,3pentadiene (Tetramethylallene) 4-Methyl-I-hexene di - 3,4-Dimethyl-2pentene 4-Methyl-cis-2hexene 4-Methyl-lrans-2hexene 3,3-Dimethylcyclopentene 2-Ethyl-3-methyl-lbutene 5-Methyl-CIS-2-hexene 9 1 5-Methyl-1.4-hexa9 1-2 5 diene 2-Methyl-I-hexene 92 0 dl- 1.3-Dimethylcyclopentene 2-Methyl-1,s-hexadiene 2,4-Dimethyl-1.3pentadiene 1.4-Dimethylcyclopentene 3-Methyl-irans-3hexene... 163 - 134 43 A 18 55 - 140 81 dl- 9 46 - 140 8 tetra- 10 7 1349 -1 35 72 139 82 A - A- 2-Ethyl-I-butene lrans-1.3-Hexadiene 3-Methylcyclopentene CIS-3-Hexene 3-Hexene (CIS-lrans mixture) trans-3-Hexene 2-Methyl-2-pentene 14 6 1455 5 150 1644 16 6-6 7 -1 31 53 A'etra- 1708 1729 -1 1343 -1 35 7 hA- 3-Methyl-trans-2pentene trans-2-Hexene 2-Hexene (CIS-trans mixture) 2.3-Hexadiene 2.3-Dimethyl-l.3butadiene :IS-2-Hexene... 2,3,4-Trimethyl-2pentene 4,4-Dimethvlcyclohexene 6-Methyl-2-heptene 2-n-Propyl-I-pentene 5-Methyl-2-heptene 3.3-Dimethylcyclohexene 2-Methyl-I-heptene 2,5-Dimethyl-1.5hexadiene -7 9 49 wlaleic anh adduct, 104 2-5 0 CC1 -8 0 -1 13 3 -8 0 5 -8 7 38 olid at -8 0, l i q at -2 3 wlercaptosuccinic acid adduct, 101 9-2 7 d I-1.2.3-Trimethylcyclopentene (Laurolene) 4-Methyl-3-heptene 3-Ethyl-2-hexene 3-Methyl-3-heptene 1-Octene - Mercaptosuccin~c... Bromc - Cyclopentene 14 24 - 135 08 dl- 1,2-Pentadiene (Ethylallene) 2.3-Pentadiene ( I 3Dimethyldllene) 4-Methyl-I-pentene 1 86 4 - 137 26 tetra- 1 27 8 - 125 26 3 88 - 153 63 3-Methyl-I-pentene 3-Methyl-1.4-pentadiene 2.3-Dimethyl-I-butene 2-Methyl-1.4-pentadiene 4-Methyl-crs-2pentene 4-Methyl-trans-2pentene 13-Hexadiene (Biallyl) 2-Methyl-I-pentene 1-Hexene i4 14 >5 -1 530 dl i5 67 i6 - 157 27 dl- 163... 5,S-Dimethyl-lhexene 125 4-Methylcyclohexene 126 3-Methylcyclohexene 127 2-Isopropyl-3methyl-I-butene 128 3,4,4-Trimethyl-Ipentene 129 3.5-Dimethyl-I-hexene 3 0 3,3-Dimethyl-1-hexene 3 1 SS-Dimethyl-trans-2hexene 32 2,4,4-Trimethyl-2pentene 33 3,3,4-Trimethyl-1pentene 34 2,2-Dimethyl-CIS-3hexene 35 1.2-Heptadiene (nButylallene) il - llll- flll- 11 11 !,%dltetra- 36 1,2-Dimethylcyclopentene 37 4-Ethylcyclopentene... Cycloheptane(Suberane) trans-1,4-Dimethylcyclohexane 1.1-Dimethylcyclohexane cis-13-Dimethylcyclohexane trans- l-Ethy l-3-methy lcyclopentane trans-l-Ethyl-2-methylcyclopentane CIS-l-Ethyl-3-methylcyclopentane I-Ethyl-1-methylcyclopentane 2.2.4.4-Tetramethylpentane l,c1 ~-2 ,~ ~-3 -Trimethylcyclopentane trans-1,2-Dimethylcyclohexane 2,2,5-Trimethylhexane CIS-1.4-Dimertlylcyclohexane trans-l,3-Dimethylcyclohexane n-Octane... 2,2,7-Trimethylbicyclo[2.2.1]heptane (a-Fenchane) 3-Ethyl-3-methylheptane 2,4-Dimethyl-kthylhexane 3,4,4-Trimethylheptane 3,3,4TrimethyIheptane 3,4,5-Trirnethylheptane 2.3-Dimethyl-i-ethylhexane 1-Methyl-3-propylcyclohexane 2,3-Dimethyloctane d,/-Pinane 2,394-Tetramethylhexane 33-Dimethyl4ethylhexane 5-Methylnonane 4-Methylnonane 3-Ethyl-2-methylheptane 3,4-Dimethyloctane d-a-Pinane d.1-l-lsopropyl-3-methylcyclohexane (d.1-m-Menthane)... (Methyldllene) 5-Methyl-1-butene ,4-Pentadiene dldl- - I36 Ethene (Ethylene) Propene (Propylene) Cyclopropene Allene 2-Methylpropene tetra- - 105 55 - 138 91 - 136 19 - 168 49 dttetraditetra - 165 22 137 56 -2 di- dl- - - 145 95 butadiene (Isoprene) I-Methvl-1,2-buta40 diene (I 1 Dimethyldllene) Zyclopentadiene 40 83 18 lgr di- - 148 28 rant-2-Pentene YY-2-Pentene I-Methyl-l-ctclobutene !-Methvl-2-butene ,4 Dinitrophenylsulfenyl... 14Carene (3,7,7-Trimethylbicyclo[2,2,l] hept-2-ene) Myrcene (2-Methyl-6methylene-2,7octadienel 58 I 61 3746 17802" 2.6-Dimethyl-2,6octadiine I-3-Carene (3,7,7-Trimethylbicyclo[2,2,l]hepi-3-ene) 3. 8-0 -Menthadiene (cis-3-Isopropenyl4-methylcyclohexene) 5-Decene 68,5614 p-8-Menthene (I-Iso propenyl-4-methylcyclohexane) d-m-8-Menthene (lIsopropenyl-3methylcyclohexane) 1-m-8-Menthene ( llsopropenyl-3methylcyclohexane) . trans-l-Ethyl-2-methylcyclopentane CIS-l-Ethyl-3-methylcyclopentane I-Ethyl-1-methylcyclopentane 2.2.4.4-Tetramethylpentane l,c1 ~-2 ,~ ~-3 -Trimethylcyclopentane trans-1,2-Dimethylcyclohexane 2,2,5-Trimethylhexane. 4-Methylnonane 3-Ethyl-2-methylheptane 3,4-Dimethyloctane d-a-Pinane d.1-l-lsopropyl-3-methylcyclohexane (d.1-m-Menthane) 2.2.3.3.4-Pentamethylpentane frans-l,2,4,S-Tetramethylcyclohexane 3.3-Diethylhexane. 3.4-Dimethyl-3-ethylhexane 3A4.4-Tetramethylhexane Cyclononane 1-lsopropyl-2-methylcyclohexane (0-Menthdne) CIS-l,2,4,5-Tetramethylcyclohexane 1-Methyl-1-propylcyclohexane 11-Decane I-Methyl-4-propylcyclohexane