Table Of ContentCRC Handbook of tables for
Organic Compound Identification
CRC HANDBOOK
of tables for
ORGANIC
COMPOUND
IDENTIFICATION
Third Edition
Compiled by
ZVI RAPPOPORT, Ph.D.
Hebrew University of Jerusalem, Israel
:V-
CRC Press, Inc.
Boca Raton, Florida
16
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12/0031150-21":"
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© 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
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
© I960 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
© 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. Cardarelli, M.S., University of Akron.
DIFFUSE REFLECTANCE SPECTROSCOPY IN ENVIRONMENTAL PROBLEM-SOLVING
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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 1967
Handbook of tables for Organic Compound Identification, © 1967 CRC
LIST OF ABBREVIATIONS USED
specific rotation um fuming pr prisms
Ma D acid j;Iac glacial purp purple
abs absolute 'lit glittering pyr pyndine
abt about ?lyc glycerol rac racemic
ac a acetic acid gran granular (or racemate)
ac anh acetic anhydride grn green reel rectangular
acet acetone , hot recr recrystallization
add addition htng heating redsh reddish
al alcohol hyd hydrate or rhomb rhombic
alk alkali hydrolyses r rapid
amor amorphous hyg , hygr hygroscopic rh rapid heating
anh anhydrous ; inactive s soluble
arom aromatic i insoluble sec secondary
aqu aqueous ign ignites scar scarcely
asym , as asymmetric msol insoluble s h slow heating
blue 1 ,L levorotatory sh short
(or L-configura- si slightly
blk black
boil boiling tion) sld solid
bp.B P boiling point leaf. If leaflets slend slender
br brown lg large sm fsmm aolill
bz benzene 'gr ligroin soft softens
brt bright hq liquid sol , soln solution(s)
brnsh brownish Ing long solv solvent(s)
Q cold It light st steel
CcQaust acabuosutitc I/Tvis- lmeacvtses sstuabbl sstuabblliemes
chl chloroform me , meth methyl sym symmetrical
cl -bz chlorobenzene micr microscopic tab , tabl tablet(s), tables
col colorless mixt mixture ten tertiary
comp compound ml milliliter tetr tetragonal
cone concentrated mod modification tol toluene
cor corrected monohyd monohydrate trans transparent
cr , cryst crystals monocl monochnic thk thick
d decomposes m p , M P melting point tncl tnchmc
d,D dextrorotatory need , nd needles trim tnmenc
(or D-configuration) 0- ortho uns unsymmetrical
dcnv derivative ol olive unst unstable
dehq deliquescent or orange vac vacuum, in vacuo
dil dilute ord ordinary V very
dist distillate org organic var variable
dk dark orth orthorhombic vic- vicinal
dl , d,l, D,L racemic oxid oxidation V1SC viscous
efflor efflorescent P- para volat volatile or volatilizes
et ethyl pa pale vlt violet
et ac ethyl acetate part partly w water
eth ether pet petroleum wh white
exp explodes pet eth petroleum ether yel yellow
fi from ph phenyl yelsh, ylsh yellowish
fl flakes ph hydraz phenyl hydrazine > above, greater than
fluores fluorescent PhNO2 nitrobenzene < below, smaller than
fp freezing point pl plates oo irascible
frz freezes powd powder xyl xylene
Handbook of tables for Organic Compound Identification, © 1967 CRC
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
Handbook of tables for Organic Compound Identification, © 1967 CRC
Handbook of tables for Organic Compound Identification, © 1967 CRC
EXPLANATIONS AND REFERENCES TO TABLE I
As a result of their inertness no general suitable derivative exists for alkanes and cycloalkanes 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 for the determination of these con-
stants
,,r*„
