Before the nineteenth century,chemists generally believed that compounds obtained from living organisms were too complex to be synthesized. According to the concept of vitalism,organic matter was endowed with a"vital force". They named these compounds"organic" and directed their investigations toward inorganic materials that seemed more easily studied. During the first half of the nineteenth century,scientists realized that organiccompounds can be synthesized in the laboratory.Around 1816 Michel Chevreulstarted a study of soaps made from various fats and alkalis.He separated the different acids that, in combination with the alkali, produced the soap.Since these were all individual compounds, he demonstrated that it was possible to make achemicalchange in various fats(which traditionally come from organic sources), producing new compounds, without"vital force".In 1828 Friedrich Wöhler produced the organic chemical urea(carbamide),a constituent of urine, from the inorganic ammonium cyanate NH，CNO，in whatis now called the Wöhlersynthesis.Although Wöhler was always cautious about claiming that he had disproved the theory of vital force,this event has often been thought of asa turning point. William Henry Perkin, while trying to manufacture quinine, accidentally manufactured the organic dye now known as Perkin's mauve. Through its great financial success, this discovery greatly increased interest in organic chemistry.The crucialbreakthrough for organic chemistry was the concept of chemical structure,developed independently and simultaneously by Friedrich August Kekulé and Archibald Scott Couper in 1858.Both men suggested that tetravalent carbon atoms could link to each other to form a carbon lattice,and that the detailed patterns of atomic bonding could be discerned by skillful interpretations of appropriate chemical reactions.
The history of organic chemistry continued with the discovery of petroleum and its separationinto fractions according to boiling ranges. The conversion of different compound types or individual compounds by various chemical processes created the petroleum chemistry leading to the birth of the petrochemical industry,which successfully manufactured artificial rubbers, the various organic adhesives, the property-modifying petroleum additives,and plastics. The pharmaceutical industry began in the last decade of the 19th century when the manufacturing of acetylsalicylic acid (more commonly referred to asaspirin)in Germany was started by Bayer. The first time a drug was systematically improved was with arsphenamine (Salvarsan). Though numerous derivatives of the dangerous toxicatoxyl were examined by Paul Ehrlich and his group, the compound with best effectiveness and toxicity characteristics was selected for production. Although early examples of organic reactions and applications were often serendipitous,the latter half of the 19th century witnessed highly systematic studies of organic compounds. Beginning in the 20th century, progress of organic chemistry allowed the synthesis of highly complex molecules via multistep procedures.Concurrently, polymers and enzymes were understood to be large organic molecules, and petroleum was shown to be of biological origin.The process of finding new synthesis routes for a given compound is called total synthesis.Total synthesis of complex naturalcompounds started with urea, and increased in complexity to glucose and terpineol.In 1907, total synthesis was commercialized for the first time by Gustaf Komppa withcamphor. Pharmaceutical benefits have been substantial. For example,cholesterol-related compounds have opened ways to synthesis complex human hormones and their modified derivatives. Since the start of the 2Oth century,complexity of total syntheses has been increasing, with examples such as lysergic acid and vitamin B12. Biochemistry has only started in the 20th century,opening up a new chapter of organic chemistry with enormous scope. Biochemistry, like organic chemistry,primarily focuses on compounds containing carbon.
The book provides authoritative and critical assessments of the many aspects oforganicchemistry.This text isespecially written with these students in mind.Thelanguage is simple explanationsclear and presentation very systematic. These will prove essential reading for organic chemistry students at the upper undergraduate level.-Editor

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1. Structure of Organic Molecules 1 Electromagnetic Spectrum· Generationg of X-rays· Monochromators·X-Ray Diffraction· Scanning Probe Microscopy (SPM)·Atomic Force Microscopy(AFM)·Scanning Tunneling Microscope(STM)·Single-crystal X-ray Diffraction·Crystallization·Theory of Diffraction·Scatteringasa Fourier Transform · X-ray Powder Diffraction ·Determination of Crystalline Phases· Crystal Structure·Linear Combinations· Crystal Systems·Crystallography and Crystal Defects·X Ray Crystallography·Crystals and X-rays·Generation of X- Rays

2. Organic Reaction Mechanism 53 Bonding to Nitrogen· Substitution and Elimination Reactions of Amines·Oxidation States of Nitrogen·Restricted Rotation·Reactions·Addition Reactions·E1 vs E2·Electrochemical Reaction Mechanism · Arrow Pushing· Homolytic Bond Cleavage·Electrophilic Aromatic Substitution·Mechanism of Nucleophilic Substitution· Substitution Reaction Mechanisms·Radical Substitution Mechanism·R-H·Reaction of Alcohols with Hydrogen Halides· Reaction of Alcohols with other Halogenating agents(SOCl2,PX3)·Nucleophilic Substitution Reactions · The SN2 Reaction

3. Chemical Reactions 118 Oxidation ofPhenols·The Chemistry ofEthers·EtherSynthesis·Reactions ofEthers·The Chemistry ofEpoxides·Cyclohexane Conformations·Methylcyclohexane Conformations·Ring Strain in Cyclopropane·Functional Group Reactions·Reactions of Alcohols· Electrophilic Substitution at Oxygen·Hydroxyl Group Substitution· Elimination Reactions · Oxidation Reactions of Alcohols· Nucleophilic Addition Reactions & Reduction · Acidity of Terminal Alkynes·Alkyl Halide Occurrence· Reactions of Alkyl Halides· Nucleophilicity· Solvent Effects · The Alkyl Moiety

4. Concept of Acids and Bases 167 Solvent-system Conception of Acids and Bases· Other Conceptions of Acids and Bases·Acid-base Equilibria·Strong and Eak Acids·The Ionic Product for Water,Kw·Strong and Weak Bases·Acid-base Indicators·Buffer Solutions·Water· Acids, Bases,and Salts·Equations for Acid-base Reactions·IUPAC Nomenclature·Lowry-Brønsted Conception of Acids and Bases

5. Analytical Techniques 215 The General Mechanism·Electrophilic Substitution Reactions not Involving PositiveIons·Comparing the Nitration ofBenzene, Nitrobenzene and Phenol·Explaining the Nitration of Benzene· The Electrophilic Substitution Mechanism· Nitration and Sulfonation ofBenzene·The Friedel-Crafts Acylation ofBenzene·An Industrial Alkylation ofBenzene·NucleophilicSubstitution at Carbon· SN1 Reaction·SN2 Reaction·Lewi's Dot Model·Valence Bond Theory· SP3 Hybridization of Carbon·SP2 Hybridization ofCarbon·SP Hybridization of Carbon·Organic Radicals·Electron Paramagnetic Resonance· Methods of Generating Free Radicals

Bibliography 257

Index 261

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