In organic chemistry, the focus is on the element carbon. Carbon is central to all living organisms; however, thousands of nonliving things are made from carbon compounds. Diamonds are carbon atoms in a crystai structute. Diamonds are so hard because the atoms of carbon are so closely bonded together in the crystal form. That same ability to pack closely together makes carbon an excellent structural element in its other forms as well. One atom of carbon can combine with up to four other atoms. Therefore, organic compounds usually are large and can have several atoms and molecules bonded together. Organic molecules can be large, and they comprise the structural components of living organisms: carbohydrates, proteins, nucleic acids, and lipids. In their outer shells, carbon atoms have four electrons that can bond with other atoms. When carbon is bonded to hydrogen, the carbon atom shares an electron with hydrogen, and hydrogen likewise shares an electron with carbon. Carbon-hydrogen molecules are referred to as hydrocarbons. Nitrogen, sulfur, and oxygen also are often joined to carbon in living organisms. Large molecules form when carbon atoms are joined together in a straight line or in rings. The longer the carbon chain, the less chemically reactive the compound is. However, in biology, other measures of reactivity are used. One example is enzymatic activity, which refers to how much more quickly a certain molecule can allow a reaction to occur.
One key to knowing that a compound is less reactive is that its melting and boiling points are high. Generally, the lower a compound's melting and boiling points, the more reactive it is. For example, the hydrocarbon methane, which is the primary component of natural gas, has just one carbon and four hydrogen atoms. Because it is the shortest carbon compound, it has the lowest boiling point (-162°C) and is a gas at room temperature. It is highly reactive. On the other hand, a compound made of an extremely long carbon chain has a boiling point of 174°C (compared to water, which has a boiling point of 100°C). Because it takes so much more for it to boil, it is much less reactive and is not gaseous at room temperature. In organic chemistry, molecules that have similar properties (whether they are chemical or physical proper ties) are grouped together. The reason they have similar properties is because they have similar groups of atoms; these groups of atoms are called functional groups. Chemical properties involve one substance changing into another substance by reacting. An example of a chemical property is the ability of chlorine gas to react explosively when mixed with sodium. The chemical reaction creates a new substance, sodium chloride. Physical properties refer to different forms of a substance, but the substance remains the same; no chemical reaction or change to a new substance occurs. Some of the properties that the functional groups provide include polarity and acidity. For example, the functional group called carboxyl (-COOH) is a weak acid. Polarity refers to one end of a molecule having a charge (polar), and the other end having no charge (nonpolar). For example, the plasma membrane has hydrophilic heads on the out side that are polar, and the hydrophobic tails (which are nonpolar) form the inside of the plasma membrane.
To come right to the point, the huge number of name reactions and reagents is really quite impressive. There is far more involved in volumes, since a great many new transformations that have been developed over the intervening time now find their way into the book. Each reaction is covered with examples from the, which is a powerful springboard for further inquiry. Unfortunately, the explanations of some of the reactions come up a bit short. As each of the reactions and reagents are treated within a relatively brief space, an unbelievable number of transformations are found within these 824 pages. This work is too comprehensive to be purely a reference book, even though it is excellent value for the money, but it will play a significant role as a reference work in the academic and professional realm.

Preface xi

VOLUME 1

A Abramovitch-Shapiro Tryptamine Synthesis • Acetalisation • Acetoacetic Ester Condensation • Achmatowicz Reaction • Acylation • Acyloin Condensation • Adams* Catalyst • Adkins Catalyst • Adkins-Peterson Reaction • Akabori Amino Acid Reaction • Alcohol Oxidation • Alder-ene Reaction • Alder-Stein Rules • Aldol Reaction • Aldol Condensation • Algar-Flynn-Oyamada Reaction • Alkylimino-de-oxo-bisubstitution • Alkyne Trimerisation • Alkyne Zipper Reaction • Allan・Robinson Reaction • Allylic Rearrangement • Amadori Rearrangement • Amine Alkylation • Angeli-Rimini Reaction • Andrussow Process • Appel Reaction • Michaelis-Arbuzov Reaction • Ai'ens-van Dorp Synthesis • Aromatic Nitration • Ai'ndt-Eistert Reaction • Auwers Synthesis • Azo Coupling 1

B Baeyer—Drewson Indigo Synthesis • Baeyer-Villiger Oxidation • Bakeland Process (Bakelite) • Baker-Venkataraman Rearrangement • Bally-Scholl Synthesis • Balz-Schiemann Reaction • Bamberger Rearrangement • Bamberger Triazine Synthesis • Bamford-Stevens Reaction • Barbier-Wieland Degradation • Bardhan-Senguph Phenanthrene Synthesis • Barfoed's Test • Bartoli Indole Synthesis • Barton Reaction • Barton-Kellogg Reaction • Barton-McCombie Deoxygenation • Barton Zard Synthesis • Barton Vinyl Iodine Orocedure • Baudisch Reaction • Baeyers Reagent • Baylis-Hillman Reaction • Bechamp Reaction • Bechamp Reduction • Beckmann Rearrangement • Bellus-Claisen Rearrangement • Belousov— Zhabotinsky Reaction • Be nary Reaction • Benedicfs Reagen t • Benkeser Reaction • Benzidine Rearrangement • Benzilic Acid Rearrangement • Benzoin Condensation • Bergman Cyclisation • Bergmann Azlactone Peptide Synthesis • Bergmann Degradation • Bergmann-Zervas Carbobenzoxy Method • Bernthsen Acridine Synthesis • Bestmann's Reagent • Betti Reaction • Biginelli Reaction • Birch Reduction • Bischler-Mohlau Indole Synthesis • Bischler-Napieralski Reaction • Biuret Test • Blaise Ketone Synthesis • Blaise Reaction • Blanc Chloromethylation • Bodroux Reaction • Bodroux-Chichibabin Aldehyde Synthesis • Bogert- Cook Synthesis • Bohn-Schmidt Reaction • Boord Olefin Synthesis • Borodin Reaction • Borsche-Drechsel Cyclization • Bosch-Meiser Urea Process • Bouveault Aldehyde Synthesis • Bouveault-Blanc Reduction • Boyland—Sims Oxidation • Boyer Reaction • Bredfs Rule • Brown Hydroboration • Bucherer Carbazole Synthesis • Bucherer Reaction • Bucherer-Bergs Reaction • Buchner Ring Expansion • Buchner-Curtius-Schlotterbeck Reaction • Buchwald- Hartwig Amination • Bunnett Reaction 73

C Cadiot-Chodkiewicz Coupling • Camps Quinoline Synthesis • Cannizzaro Reaction • Carbohydrate Acetalisation • Carbonyl Reduction • Carbonylation • Carroll Rearrangement • Castro- Stephens Coupling • Catalytic Reforming • Corey-Itsuno Reduction • Chan-Lam Coupling • Cheletropic Reaction • Chichibabin Reaction • Chichibabin Pyridine Synthesis • Chiral Pool Synthesis • Chugaev Elimination • Ciamician-Dennstedt Rearrangement • Conrad-Limpach Synthesis • Cope Reaction • Cope Rearrangement • CBS catalyst • Coupling Reaction • Criegee Rearrangement • Cross Meta thesis • Crum Brown-Gibson Rule • Curtius Rearrangement • Cyanohydrin Reaction 208

VOLUME 2

D Dakin Oxidation • Dehydration Reaction • Demjanov Rearrangement • Dess-Martin Periodinane • Diazonium Compound • Dieckmann Condensation • Diels Reese Reaction • Directed Ortho Metallation • Doebner-Miller Reaction • Dichlorocarbene • Dowd-Beckwith Ring Expansion Reaction • Duff Reaction • Dyotropic Reaction 273

E ElcB Elimination Reaction • Eglinton Reaction • Elbs Persulfate Oxidation • Elbs Reaction • Electrocyclic Reaction • Elimination Reaction • Ene Reaction • Étard Reaction 314

F Favourskii Reaction • Fenton's Reagent • Fischer Indole Synthesis • Fischer—Tropsch Process • Forster-Decker Method 366

G Gabriel Synthesis • Gassman Indole Synthesis • Gattermann- Koch Reaction • Gattermann Reaction • Gilman Reagent • Gould- Jacobs Reaction • Grignard Reaction • Guerbet Reaction 388

H Haloform Reaction • Halogen Addition Reaction • Hammick Reaction • Haber-Weiss Reaction • Haworth Reactions • Heck Reaction • Hydration Reaction • Hinsberg Reaction • Hydrocarbon cracking 404

I Ing-Manske Procedure • Ipso Substitution • Ishikawa Reagent • Isomer • Ivanov Reaction 438

J Jacobsen Rearrangement • Janovsky reaction • Japp-Klingemann Reaction • Johnson-Claisen Rearrangement • Julia Olefination 449

K Kabachnik-Fields Reaction • Kiliani—Fischer Synthesis • Kindler Reaction • Knorr pyrazole synthesis • Koenigs-Knorr Reaction • Krohnke Pyridine Synthesis 461

L Larock Indole Synthesis • Lebedev Process • Lehmstedt-Tanasescu Reaction • Letts Nitrile Synthesis • Leuckart Reaction • Levinstein Process • Lindlar Catalyst • Lucas* Reagent • Luche Reduction 491

M Maillard Reaction • Madelung Synthesis • Malaprade Reaction • Mannich Reaction • Martinet Dioxindole Synthesis • McFadyen- Stevens Reaction • McMurry Reaction • Menshutkin Reaction • Michael Reaction • Miyaura Borylation Reaction • Mitsunobu Reaction • Molisch's Test • Mukaiyama Aldol Addition • Myers- Saito Cyclization 510

VOLUME 3

N Nametkin Rearrangement • Nazarov Cyclisation Reaction • Nef Reaction • Nicholas Reaction • Nitroaldol Reaction • Noyori Asymmetric Hydrogenation 537

O Ohira-Bestmann reaction • Olah Reagent • Oppenauer Oxidation • Ostromyslenskii reaction • Oxo Synthesis • Oxymercuration Reaction • Ozonolysis 579

P Paal-Knorr Synthesis • Passerini Reaction • Paternò-Büchi Reaction • Pauson-Khand Reaction • Pelouze Synthesis • Perkin Reaction • Perkow Reaction • Petasis Reaction • Peterson Olefination • Pfitzinger Reaction • Phenanthridine • Pictet— Spengler Reaction • Piria Reaction • Piria Reaction • Prileschajew Reaction • Pschorr Reaction • Pschorr Reaction • Pummerer Rearrangemen 604

Q Quelet Reaction 655

R Ramberg—Backlund Reaction • Rauhut—Currier Reaction • Reed Reaction • Reformatsky Reaction • Reimer—Tiemann Reaction • Reissert Indole Synthesis • Reissert Reaction • Reppe Synthesis • Riley oxidations • Ritter Reaction • Rosenmund Reduction • Rothemund Synthesis 656

S Sandmeyer Reaction • Schiff Base • Sakurai Reaction • Schmidt Reaction • Scholl Reaction • Shapiro Reaction • ShenckEne Eeaction • Stetter Reaction • Swarts Reaction 675

T Tamao Oxidation • Tafel Rearrangement • Ter Meer Reaction • Thiele Reaction • Thiol-yne Reaction • Thorpe Reaction • Tiemann Rearrangement • Tollens' Reagent • Transfer Hydrogenation • Traube Purine Synthesis • Tscherniac-Einhorn Reaction • Tschitschibabin Reaction 702

U Ugi Reaction • Upjohn Dihydroxylation • Urech Cyanohydrin Met hod • Urech Hydantoin Synthesis 744

V Varrentrapp Reaction • Vilsmeier—Haack Reaction • Von Braun Amide Degradation • Von Braun Reaction • Von Richter Cinnoline Synt hesis • Von Richter Reaction 753

W Wacker-Tsuji Oxidation • Wagner-Jauregg Reaction • Wallach Rearrangement • Wenker Synthesis • Weinreb Ketone Synthesis • Wessely-Moser Rearrangement • Wharton Reaction • Whiting Reaction • Wittig Reaction • Wohl Degradation • Wohl-Aue Reaction • Wohler Synthesis • Wohl-Ziegler Bromination • Wolffenstein-Böters Reaction • Wolff Rearrangement • Wolff-Kishner Reduction • Woodward—Hoffmann Rules • Wurtz Reaction • Wurtz-Fittig Reaction 759

Y Yamaguchi Esterification 794

Z Zeisel Determination • Zerewitinoff Determination • Ziegler Condensation • Zimmermann Reaction • Zincke Nitration • Zincke Reaction • Zincke-Suhl reaction 796

Bibliography 813

Index 817

Frank Rivera received Ph.D.in Organic Chemistry from University of Maryland, Baltimore. He teaches Sophomore Organic Chemistry and Advanced Organic Chemistry.His areas of research are: Photochemistry and Optical Spectroscopy,Theoretical and Computational Chemistry, Dynamics of reactive and inelastic collisions involving open-shell atoms and small molecules;rotational,vibrational, and electronic energy transfer,photodissociation and photodetachment of small systems; linear algebra algorithm development for GPU and mixed GPU/CPU architecture.

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