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ORGANIC CHEMISTRY

OR

CHEMISTRY OF THE CARBON COMPOUNDS



BY

VICTOR VON RICHTER

|

EDITED BY PROF. R. ANSCHUTZ AND PROF. G. SCHROETER



VOLUME I
CHEMISTRY OF THE ALIPHATIC SERIES



NEWLY TRANSLATED AND REVISED FROM THE GERMAN EDITION
(AFTER PROF. EDGAR F. SMITH'S THIRD AMERICAN EDITION)

BY

PERCY E. SPIELMANN, PH.D., B.SC., F.I.C., A.R.C.SC.



SECOND (REVISED) EDITION



PHILADELPHIA:

P. BLAKISTON'S SON & CO
1012 WALNUT STREET

1919



PREFACE TO THE FIRST ENGLISH
EDITION

A COMPARISON between the present work, the latest edition of the
German original, and the last American translation, will show that
while the German text-book has been faithfully followed, modifications
have been introduced which will be regarded, it is hoped, in the light
of solid improvement. Certain statements have been corrected or
modified, changes which have usually been indicated, and a great
number of minor alterations have been made in the marshalling of
facts and the setting out of formulae with the object of a more logical
sequence and a clearer emphasis of the point under discussion.

References to German literature have been retained with the
object of preserving to the student the advantages of the origin of the
book ; the English references will be otherwise readily obtainable
by him.

I take great pleasure in expressing my gratitude to Mr. W. P.
Skertchly, F.I.C., not only for assistance in the more mechinical part
of the translation, but also for the careful way in which he has read
through the proofs.

Furthermore, to Mr. A. J. Greenaway, Sub-Editor of the Journal
of the Chemical Society, I offer my most cordial thanks for his valued
advice on certain doubtful points of nomenclature.

PERCY E. SPIELMANN.
LONDON, 1915.



N.B. The Publishers beg to explain that a year's delay has
occurred in the production of this volume (announced for the autumn
of 1914), owing to Dr. Spielmann's employment on important work
connected with explosives for the Government.

K. P. T. T. & Co., LTD.



PREFACE TO THE SECOND ENGLISH
EDITION

NOTWITHSTANDING the depletion of students from the many Technical
Institutions as a result of the late war, a second edition of the first
volume of this text-book has been called for a gratifying recognition
of its continued and increasing usefulness.

As inevitable to the first production of a book of this character,
with its innumerable formulae and figures, a certain number of mis-
prints had crept in, and a careful search for these has been made.

The need of such rectifications must not deter me from paying a
tribute to the printers, Messrs. Clowes and Sons, for the care and success
with which they have carried through so complicated a piece of type
setting ; while to the Publishers is due acknowledgment for much
that was of assistance in my share of the work of production.

It is believed that, in its revised form, this volume will be found to
meet all the requirements of the daily expanding class of chemical
students, on whose services will depend so important a share in the
scientific foundation of the firm establishment and success of British
Industry.

PERCY E. SPIELMANN.
LONDON, 1919.



PREFACE TO THE THIRD AMERICAN

EDITION

IN presenting this translation of the eighth German edition of
v. Richter's " Organic Chemistry " the writer has little to add to what
has previously been expressed in the prefaces to the preceding American
editions of this most successful book. The student of the present
edition will, however, very quickly discover that the subject-matter,
so ably edited by Professor Anschiitz, is vastly different from that
given in the earlier editions. Indeed, the book has sustained very
radical changes in many particulars, and certainly to its decided
advantage. The marvellous advances in the various lines of synthetic
organic chemistry have made many of the changes in the text abso-
lutely necessary, and for practical reasons it has seemed best to issue
this new edition in two volumes.

Eminent authorities, such as Profs, v. Baeyer, E. Fischer, Waitz,
Claisen, and others, have given the editor the benefit of their super-
vision of chapters relating to special fields of investigation in which
they are the recognized authorities.

The translator here acknowledges his great indebtedness to his
publishers, P. Blakiston's Son & Co., for their constant aid in his work,
as well as to Messrs. Wm. F. Fell & Co., for the care they have taken
and the skill they have displayed in the composition of what will
generally be admitted to be a difficult piece of typography.

E. F. SMITH.



PREFACE TO THE SECOND AMERICAN

EDITION

THE present American edition of v. Richter's " Organic Chemistry "
will be found to differ very considerably, in its arrangement and size,
from the first edition. The introduction contains new and valuable
additions upon analysis, the determination of molecular weights,
recent theories on chemical structure, electric conductivity, etc.
The section devoted to the carbohydrates has been entirety rewritten,
and presents the most recent views in regard to the constitution of



viii PREFACES

this interesting group of compounds. The sections relating to the
trimethylene, tetramethylene, and pentamethylene series, the fur-
furane, pyrrol, and thiophene derivatives, have been greatly enlarged,
while the subsequent chapters, devoted to the discussion of the
aromatic compounds, are quite exhaustive in their treatment of special
and important groups. Such eminent authorities as Profs. Ostwald,
von Baeyer, and Emil Fischer have kindly supervised the author's
presentation of the material drawn from their special fields of
investigation.

The characteristic features of the first edition have been retained,
so that the work will continue to be available as a text-book for
general class purposes, useful and reliable as a guide in the preparation
of organic compounds, and well arranged and satisfactory as a refer-
ence volume for the advanced student as well as for the practical
chemist.

The translator would here express his sincere thanks to Prof. v.
Richter, whose hearty co-operation has made it possible for him to
issue this translation so soon after the appearance of the sixth German
edition.

E. F. SMITH.



PREFACE TO THE FIRST AMERICAN
EDITION

THE favourable reception of the American translation of Prof, von
Richter 's " Inorganic Chemistry " has led to this translation of the
" Chemistry of the Compounds of Carbon/' by the same author. In
it will be found an unusually large amount of material, necessitated
by the rapid advances in this department of chemical science. The
portions of the work which suffice for an outline of the science are
presented in large type, while in the smaller print is given equally
important matter for the advanced student. Frequent supplementary
references are made to the various journals containing original articles,
in which details in methods and fuller descriptions of properties, etc.,
may be found. The volume thus arranged will answer not only as
a text -book, and indeed as a reference volume, but also as a guide
in carrying out work in the organic laboratory. To this end numerous
methods are given for the preparation of the most important and the
most characteristic derivatives of the different classes of bodies.

E. F. SMITH.



ABBREVIATIONS

A. , Liebig's Annalen der Chemie. Spl. Supplementband.

A. chim. phys. . . Annales de chemie et de physique.

Am. .... American Chemical Journal.

Anorg. Ch. . . . Richter-Klinger, Lehrbuch der anorganischen Chemie.

Richter-Smich, Text-book of Inorganic Chemistry.

Arch. exp. Path. . . Archiv fur experimentelle Pathologic und Pharmakologie.
Arch. ges. Phys. . . Archiv fur die gesammte Physiologic.
[a] D .... Specific optical rotation.
B ..... Berichte der deatschen chemischen Gesellschaft.

R = Referate.
Bp. .... Boiling point. Bp 10 = Boiling point at 10 mm. pressure of

mercury.

Bull. soc. chim. . . Bulletin de ia societe chimique de Paris.
C. .... Chemisches Centralblatt.
Ch. Ztg. . . . Chemiker-Zeitung.
C.r. .... Comptes rendus des seances de 1'Academie des science?.



Density, specific gravity, D 20 = Sp. gr. at 20 C.

A 1 , A 2 , A 3 , etc. . . Denotes the position of a double linkage in a carbon chain,

reckoned from the C-atom I, 2, 3, etc. to the next

higher member.

D. R. P. . . . Deutsches Reichspatent.

Gaz. chim. ital. . . Gazetta chimica italiana.

F. Ildw. . . . Fehling's Handworterbuch fur Chemie.

jf. .... Jahresbericht fur die Fortschritte der Chernie.

y. Chem. Soc. . . Journal of the Chemical Society.

J. pr. C/i., or y. /;-. Ch.

N. F. . . . Journal fur praktische Chemie. Neue Folge.

Z. Hdw. . . . Ladenburg's Handworterbuch fur Chemie.

M. Monatshefte fiir Chemie.

Pharm. Centr. . . Pharmaceutische Centralhalle.

Phil. Mag. . . . Philosophical Magazine.

Pogg. A., or Wied, A. . Annalen der Physik und Chemie, published by Poggendorf ;

or new series, published by Wiedemann.

R ..... S*rB.

R. Meyer's J. . Richard Meyer's Jahrbuch der Chemie.

Wied. A. . . See Pogg. A.

Wien. Monatsh. . Monatsheft fur chemie (Vienna).

Z. . Zeitschrift fur Chemie.

Z. anal. Ch. . . Zeitschrift fur analytische Chemie.

Z. angew. Ch. . Zeitschrift fur angewandte Chemie.

Z. anorg. Ch. . Zeitschrift fur anorganische Chemie.

Z. Electroch. . . Zeitschri't fur Electrochemie.

Z. Kryst. . . Zeitschrift fur Krystallographie und Mineralogie.

Z.fhys. Ch. . . Zeitschrift fiir physicalische Chemie.

Z. phystol. Ch. , Hoppe-Seyler's Zeitschrift fiir physiologische Chemie.



CONTENTS



INTRODUCTION



Determination of the Composition of Carbon Compounds

Determination of the Molecular Formula .

The Chemical Constitution of the Carbon Compounds

The Nomenclature of the Carbon Compounds .

Physical Properties of the Carbon Compounds .

Heat of Combustion of Carbon Compounds

Action of Heat, Light, and Electricity upon Carbon Compounds

The Direct Combination of Carbon with other Elements

Classification of the Carbon Compounds . . .











PAG*

2










9










18










42










43










60


ounds








61










11



I. FATTY COMPOUNDS, ALIPHATIC SUBSTANCES
OR METHANE DERIVATIVES, CHAIN OR
ACYCLIC CARBON DERIVATIVES .... 69

I. HYDROCARBONS . . . . 69

A. Saturated or Limit Hydrocarbons, Paraffins, Alkanes, Marsh Gas or Methane

Hydrocarbons ........... 69

B. Unsaturated Hydrocarbons. I. Olefines or Alkylenes, 79 ; 2. Acetylenes or

Alkines, 85 ; 3. Diolefines, 90; 4. Olefine Acetylenes, 91 ; 5. Diacetylenes,

91 ; 6. Triolefines .......... 91



II. HALOGEN DERIVATIVES OF THE HYDROCARBONS 91



OXYGEN DERIVATIVES OF THE METHANE
HYDROCARBONS



98



III. THE MONOHYDRIC ALCOHOLS AND THEIR
OXIDATION PRODUCTS



100

109



I. Monohydric Alcohols, 100. A. Saturated Alcohols, Paraffin Alcohols .

B. Unsaturated Alcohols, 123. I. Olefine Alcohols, 123 ; 2. Acetylene

Alcohols, 125 ; 3. Diolefine Alcohols 125

Alcohol Derivatives. I. Simple and Mixed Ethers, 125 ; 2. Esters of
the Mineral Acids, 130; 3. Sulphur Derivatives of the Alcohol

Radicals 142

4. Selenium and Tellurium Compounds ...... 148

>. Nitrogen Derivatives of the Alcohol Radicals ..... 148

Phosphorus Derivatives of the Alcohol Radicals ..... 173



I:



xii CONTENTS

PAGE

7. Alkyl Derivatives of Arsenic, 175 ; 8. Antimony, 179 ; 9. of Bismuth,

179; 10. of Boron, 180; n. of Silicon, 180 ; 12. of Germanium . 181

13. Tin Alkyl Compounds ......... 182

14. Metallo-organic Compounds . . . . . . . .183

2. Aldehydes, and 3. Ketones ......... 189

2A. Aldehydes of the Saturated Series 191

1. Halogen Substitution Products of the Saturated Aldehydes . 201
Peroxides of the Aldehydes ....... 203

2. Ethers and Esters of Methylene and Ethylidene Glycols . . 204

3. Sulphur Derivatives of the Saturated aldehydes . . . 208

4. Nitrogen Derivatives of the Aldehydes ..... 210
2B. Olefine Aldehydes ......... 214

2C. Acetylene Aldehydes 215

3 A. Ketones of the Saturated Series . . . . ... .216

1. Halogen Substitution Products of the Ketones .... 224

2. Alkyl Ethers of the Ortho-ketones 225

3. Ketone Halides 225

4. Ketone Bisulphites and Sulphoxylates . . . . .225

5. Sulphur Derivatives of the Saturated Ketones .... 225

6. Nitrogen Derivatives of the Ketones ..... 226

38. Olefine and Diolefine Ketones 228

3C. Acetylene Ketones ......... 232

4. Monobasic Carboxylic Acids ......... 232

A. Monobasic Saturated Acids . . . . . . . .235

Derivatives of the Fatty Acids 265

1. Esters of the Fatty Acids ....... 265

2. Acid Halides of the Fatty Acids . . . . . 269

3. Acid Anhydrides . . . . . . . .271

4. Acid Peroxides ......... 273

5. Thio-Acids ......... 273

6. Acid Amides ......... 274

7. Acid Hydrazides ........ 278

8. Acid Azides ......... 278

9. Fatty Acid Nitriles 278

10. Amide Chlorides ........ 281

11. Imide Chlorides 281

12. Imido-Ethers % ..." 281

13. Thiamides 281

14. '1 hio-imido-Ethers ........ 282

15. Amidines .......... 282

16. Hydroxamic Acids ........ 282

17. Hydroximic Acid Chlorides ...... 283

18. Nitrolic Acids ......... 283

19. Amidoximes or Oxamidines ....... 283

20,21. Hydroxamic Oxime ; Nitrosoximes ..... 284

22, 23. Hydrazidine and Hydrazo-oxime ..... 284

24. Ortho-fatty Acid Derivatives 284

Halogen Substitution Products of the Fatty Acids . . . 284

B. Oleic Acids, Olefine Monocarboxylic Acids 290

C. Acetylene Carboxylic Acids ........ 302

D. Diolefine Carboxylic Acids 305



IV. DIHYDRIC ALCOHOLS OR GLYCOLS, AND

THEIR OXIDAT1QN PRODUCTS . . 306

I. Dihydric Alcohols or Glycols 307

Glycol Derivatives . . . . . . . . . .316

1. Alcohol Ethers of the Glycols . . . . .316

2. Esters of the Dihydric Alcohols . . . . . . 319

3. '1 hio-Compounds of Ethylene Glycols ...'.. 324

4. Nitrogen Derivatives of the Glycols ...... 327



CONTENTS xiii



2. Aldehyde-Alcohols, 337 ; Nitrogen-containing Derivatives of the Aldehyde-

Alcohols ............ 339

3. Ketone-Alcohols or Ketols, 340 ; Nitrogen-containing Derivatives of the

Ketone-Alcohols ........... 344

4. Dialdehydes ........... . 346

5. Ketone-Aldehydes, or Aldehyde- Ketones ....... 348

6. Diketones, 348 ; Nitrogen-containing Derivatives of the Dialdehydes, Alde-

hyde-Ketones and Diketones . . . . . . . 353

7. Alcohol- or Hydroxy-acids ......... 356

A. Saturated Ilydroxymonocarboxylic Acids, 362 ; o-Hydroxy-acids, 362 ;

/3-Hydroxycarbpxylic Acids, 369; 7- and 0-Hydroxy-acids, 371 ;
Sulphur Derivatives of the Hydroxy-acids, 376 ; Nitrogen Derivatives
of the Hydroxy-acids, 378 ; Amino-Fatty Acids, 385 j Dipeptides
and Polypeptides ......... 390

B. Unsaturated Hydroxy-acids, Hydroxy-olefine Carboxylic Acids . . 397

8. Aldehyde-acids, 400 ; Nitrogen Derivatives of the Aldehyde-acids . . . 402

9. Ketonic Carboxylic Acids .......... 406

A, Saturated Ketone Carboxylic Acids. I. o-Ketonic Acids, 407 ; Nitrogen

Derivatives of the o-Ketonic Acids, 409. II. /3-Ketonic Acids, 410 ;
Acetoacetic Acid, 410 ; Nitrogen Derivatives of 0-Ketonic Acid,
419 ; Halogen Substitution Products of the j8-Ketonic Esters, 420.
III. 7-Ketonic Acids, 421 ; Nitrogen Derivatives of the 7-Ketonic
Acids, 423. IV. 5-Ketonic Acids 424

B. Unsaturated Ketonic Acids ; Olefine Ketonic Acids .... 425

CARBONIC ACID AND ITS DERIVATIVES . . 425

Chlorides of Carbonic Acid, 430 ; Sulphur Derivatives of Ordinary Carbonic
Acid -431

Amide Derivatives of Carbonic Acid, 435; Carbamide Urea, 418 ; Ure'ides,
441 ; Hydrazine-, Azine-, and Azido-Derivatives of Carbonic Acid, 446 ;
Sulphur-containing Derivatives of Carbamic Acid and of Urea . . . 448

Guanidine and its Derivatives ......... 454

Nitriles and Imides of Carbonic and Thiocarbonic Acids, 459 ; Oxygen Deriva-
tives of Cyanogen, their Isomerides and Polymerides, 460 ; Halogen Com-
pounds of Cyanogen and its Polymers, 465 ; Sulphur Compounds of
Cyanogen, their Isomers and Polymers, 466 ; Cyanamide and the Amides
of Cyanuric Acid, 471 ; Ketenes ........ 474

10. Dibasic Acid, Dicarboxylic Acids ........ 476

A. Paraffin Dicarboxylic Acids, 476 ; Oxalic Acid and its Derivatives, 480 ;

Nitriles of Oxalic Acid, 484 ; the Malonic Acid Group, 487 ; Carbon
Suboxide, 488 ; Ethylene Succinic Acid Group, 491 ; Nitrogen-
containing Derivatives of the Ethylene Succinic Acid Group, 496 ;
Halogen Substitution Products of the Succinic Acid Group, 499 ;
Glutaric Acid Group, 501 ; Group of Adipic Acid and Higher
Normal Paraffin Dicarboxylic Acids ...... 504

B. Olefine Dicarboxylic Acids, 507 ; Fumaric Acid, 509 ; Maleic Acid,

510; The Isomerism of Fumaric and Maleic Acids, 512; Itaconic
Acid, 515 ; Citraconic Acid, 516; Mesaconic Acid . . . 516



V. TRIHYDRIC ALCOHOLS: GLYCEROLS AND

THEIR OXIDATION PRODUCTS . . 523

1. Trihydric Alcohols, 524. A. Glycerol Esters of Inorganic Acids, 529. B.

Glycerol Fatty Acid Esters, Glycerides, 530; Glycerol Ethers, 531;

Nitrogen Derivatives of the Glycerols . ... 533

2. Dihydroxy-Aldehydes . . ' . . 533

3. Dihydroxy-Ketones (Oxetones) ...... 534

4. Hydroxy-Dialdehydes ........ 535

5. Hydroxy- Aldehyde Ketones 53 6



xiv CONTENTS

6. Hydroxy-Ketones . ......... 536

7. Dialdehyde Ketones .......... 537

8. Aldehyde Diketones . 537

9. Triketones ............ 537

10. Dihydroxy-monocarboxylic Acids, 538 ; Monoamino-hydroxy-carboxylic Acids,

540 ; Monoamino-thio-carboxylic Acids, 541 ; Diamino-monocarboxylic
Acids, 542 ; Dihydroxy-olefine Monocarboxylic Acids .... 543

11, 12. Aldo-hydroxy-carboxylic Acids, and Hydroxy-keto-carboxylic Acids . 543

13. Aldehydo-ketone Carboxylic Acids . 545

14. Diketo-carboxylic Acids .......... 546

15. Monohydroxy-dicarboxylic Acids. %

A. Monohydroxy- Paraffin D-carboxylic Acids ..... 548

Hydroxymalonic Acid Group ........ 549

Hydroxysuccinic Acid Group . . . . . . . . 551

Aminosuccinic Acids ......... 553

Hydroxyglutaric Acid Group ........ 558

B. and C. Hydroxy-olefine Carboxylic Acids and Hydroxy-olefine Dicar-

boxylic Acids .......... 560

16. Aldodicarboxylic Acids. A. j8-Aldodicarboxylic Acids, 561. B. 7-Aldodi-

carboxylic Acids ........... 561

17. Ketone-dicarboxylic Acids, 562 ; Ketomalonic Acid Group, 562 ; Nitrogen

Derivatives of Mesoxalic Acid, 563; Ketosuccinic Acid Group, 564;
Nitrogen Derivatives of Oxalacetic Acid, 567 ; Ketoglutaric Acid Group,
568 ; Olefine- and Di-olefine-Ketone Dicarboxylic Acids . . . -571
Uric Acid Group: Urei'des or Carbamides of Aldehyd- and Keto-Mono-
carboxylic Acids, 572 ; Ure'ides or Carbamides of Uicarboxylic Acids, 575 ;
Diureides, 580 ; Oxidation of Uric Acid, 584 ; Synthesis of Uric Acid, 585 ;
Conversion of Uric Acid into Xanthine, Guanine, Hypoxanthine and
Adenine, 587 ; Synthesis of Heteroxanthine, Theobromine, and Paraxan-
thine 590

18. Tricarboxylic Acids: A. Saturated TricarboxyHc Acids, 592; B. Olefine

Tricarboxylic Acids 594



VI. TETRAHYDRIC ALCOHOLS AND THEIR

OXIDATION PRODUCTS ... 595

1 . Tetrahydric Alcohols . . . / 596

2. Trihydroxyaldehydes ; 3. Trihydroxyketones - 597

4. Hydroxytriketones ........... 597

5. Tetraketones 597

6. Trihydroxy-monocarboxylic Acids ........ 598

7. Dihydroxyketo-monocarboxylic Acids . . ... . . . 598

8. Hydroxydiketo-carboxylic Acids ... .... 598

9. Triketo-monocarboxylic Acids ......... 598

10. Dihydrpxy-dicarboxylic Acids : A. Malorric Acid Derivatives, 599 ; B.

Succinic Acid Derivatives, 599 ; Synthesis of Racemic Acid, 601 ; C.
Glutaric Acid Derivatives, 605 ; D. Adipic Acid Derivatives and Higher

Homologues ........... 606

11. Hydro xy-keto-dicarbpxylic Acids . 607



Diketone Dicarboxylic Acids

13. Hydroxytricarboxylic Acids

14. Ketone Tricarboxylic Acids ......

15. Tetracarboxylic Acids : A. Paraffin Tetracarboxylic Acids, 613

Tctracarboxylic Acids .......



B. Olefine



607
610
612

615



CONTENTS



xv



VII. THE PENTAHYDRIC ALCOHOLS OR PEN-
TITOLS AND THEIR OXIDATION PRODUCTS.



615



I. Pentahydric Alcohols, Pentitols .
2. Tetrahyclroxyaldehydes, Aldopentoses
3. Tetrahydroxymonocarboxylic Acids
4. Trihydroxydicarboxylic Acids
5. Dihydroxy-ketone Dicarboxylic Acids
6. Triketone Dicarboxylic Aci-ls
7. Dihydroxytricarboxylic Acids
















615
616
619
621
621
621
621
622



VIII. HEXA- AND POLY-HYDRIC ALCOHOLS
AND THEIR OXIDATION PRODUCTS .



622



I A. Hexhydric Alcohols, Hexahydroxyparaffins, Hexitols .... 622

I B. Heptahydric Alcohols .......... 624

I C. Octahydric Alcohols 625

1 D. Nonohydric Alcohols .......... 625

2, 3. Penta-,* Hexa-, Hepta-, and Octo-Hydroxynldehydes and Ketones . . 625

2 A. Pentahydroxyaldehydes, and 3 A. Pentahydroxyketones, Hexoses, Dextroses

(Glucoses), Monoses .......... 626

2 A. Aldohexoses ............ 631

3 A. Ketohexoses 635

2 B. Aldoheptoses ; 2 C. Aldo-octoses ; 2 D. Aldononoses .... 637

The synthesis of Grape-sugar or d-Dextrose, and of Fruit-sugar or d-Fructose. 637

A. The Space-Isornerism of the Pentitols and Pentoses, the Hexitols and

Hexoses 639

B. The Space-Isomerism of the Simplest Hexitols and the Sugar-Acids, the

Aldohexoses and the Gluconic Acids ...... 641

Derivation of the Space-formula for d-Dextrose or Grape-sugar . . 643

Derivation of the Configuration of d-Tartaric Acid .... 646



Hexaketones ............ 647

647
647

651
651
652
652

652



5. Polyhydroxymonocarboxylic Acids

A. Pentahydroxycarboxylic Acids .......

B.' Hexose Carboxylic Acids, Hexahydroxymonocarboxylic Acids

C. Aldoheptose Carboxylic Acids, Heptahydroxycarboxylic Acids

D. Aldo-octose Carboxylic Acids, Octohydroxycarboxylic Acids

6. Tetrahydroxy- and Pentahydroxy-Aldehyde Acids .

7. Monoketotetrahydroxycarboxylic Acids ......

8. Poly hydroxydicarboxy lie Acids: A. Tetrahydroxydicarboxylic Acids,

B. Pentahydroxydicarboxylic Acids .

9. Tetraketodicarboxylic Acids

10. Triketo-tricarboxylic Acids ........

11. Hydroxyketotetracarboxylic Acids

12. Diketotetracarboxylic Acids



652



655
655
655



Appendix : Higher Polycarboxylic Ethyl Esters



656



CARBOHYDRATES



656



A. Disaccharides ; Saccharobioses . . . , . . 657

B. Trisaccharides ; Saccharotrioses 661

C. Polysaccharides, 66 1 ; Nitrocelluloses 664



xvi CONTENTS

PACK

ANIMAL SUBSTANCES OF UNKNOWN CONSTITUTION 665

Proteins, Albumins, 666 ; a Monamino-monocarboxylie Acids, 666 ; b Mon-
amino-dicarboxylic Acids, 666 ; c Hydroxamino, Thioamino-, Dianimo-?

Imino-Acids ............ 667

A. Glucoproteins 071

B. Phosphoproteins 672

C. Gelatin (Derivatives of Intercellular Materials) . . " . . . . 673

D. Haemoglobins, 674 ; Chlorophyll ....... 675

K. Biliary Substances ........... 676

F. Unorganized Ferments or Enzymes ........ 677

INDEX 679



A TEXT-BOOK



OF



ORGANIC CHEMISTRY



INTRODUCTION

WHILST inorganic chemistry was developed primarily through the
investigation of minerals, and was in consequence termed mineral
chemistry, it may be said that the development of organic chemistry
was due to the study of products resulting from the alteration of plant
and animal substances. About the close of the eighteenth century
Lavoisier demonstrated that, when the organic substances present in
vegetable and animal organisms were burned, carbon dioxide and
water were always formed. It was this chemist also who showed that
the component elements of these bodies, so different in properties,
were generally carbon, hydrogen, oxygen, and, especially in animal
substances, nitrogen. Lavoisier further gave utterance to the opinion
that peculiarly constituted atomic groups, or radicals, were to be
accepted as present in organic substances ; whilst the mineral sub-
stances were regarded by him as the direct combinations of single
elements.

As it seemed impossible, for a long time, to prepare organic bodies
synthetically from the elements, the opinion prevailed that there
existed an essential difference between organic and inorganic sub-
stances, which led to the use of the names Organic Chemistry and
Inorganic Chemistry. The prevalent opinion was, that the chemical
elements in the living bodies were subject to other laws than those in
the so-called inanimate nature, and that the organic substances were
formed in the organism only by the intervention of a peculiar vital
force, and that they could not possibly be prepared in an artificial
way.

One fact sufficed to prove these rather restricted views to be un-
founded. The first organic substance artificially prepared was urea
{Wohler, 1828). By this synthesis chiefly, to which others were soon
added, the idea of a peculiar force necessary to the formation of organic



Online LibraryVictor von RichterOrganic chemistry, or : Chemistry of the carbon compounds (Volume 1) → online text (page 1 of 100)