ORGANIC CHEMISTRY: AN INTERMEDIATE TEXT
CONTENTS 1 FUNCTIONAL GROUPS AND CHEMICAL BONDING FUNCTIONAL GROUPS / ORBITALS / BONDING SCHEMES / ANTIBONDING ORBITALS / RESONANCE / CONJUGATED ? SYSTEMS / AROMATICITY / BIBLIOGRAPHY / PROBLEMS / 2 OXIDATION STATES OF ORGANIC COMPOUNDS OXIDATION LEVELS / OXIDATION STATES IN ALKANES / OXIDATION STATES IN ALKENES / OXIDATION STATES IN COMMON FUNCTIONAL GROUPS / OXIDATION LEVEL CHANGES DURING REACTIONS / 3 ACIDITY AND BASICITY BRONSTED AND LEWIS ACIDS AND BASES / ACID STRENGTH / ACID–BASE EQUILIBRIA / AMPHOTERIC COMPOUNDS / STRUCTURAL EFFECTS ON ACIDITY / ELECTRONEGATIVITY / INDUCTIVE EFFECTS / RESONANCE EFFECTS / 4 CURVED-ARROW NOTATION ELECTRON MOVEMENT / HETEROLYTIC BOND CLEAVAGES / HETEROLYTIC BOND FORMATION / HOMOLYTIC BOND MAKING AND BOND BREAKING / RESONANCE STRUCTURES / DEPICTION OF MECHANISM / 5 MECHANISMS OF ORGANIC REACTIONS ACTIVATION ENERGY / ACTIVATED COMPLEX / REACTION ENERGETICS / STRUCTURE OF THE ACTIVATED COMPLEX / HAMMOND POSTULATE / REACTION KINETICS / DETERMINING ACTIVATION ENERGIES / ISOTOPE EFFECTS / ELECTRONIC EFFECTS / HAMMETT EQUATION / 6 STEREOCHEMICAL AND CONFORMATIONAL ISOMERISM STEREOCHEMICAL STRUCTURES / CHIRALITY / CON?GURATION OF CHIRAL CENTERS / MULTIPLE STEREOCENTERS / OPTICAL ACTIVITY / ABSOLUTE CON?GURATION / PHYSICAL PROPERTIES OF ENANTIOMERS / RESOLUTION OF ENANTIOMERS / STEREOSELECTIVE REACTIONS / FORMATION OF ENANTIOMERS / FORMATION OF DIASTEREOMERS / STEREOCHEMISTRY TO DEDUCE MECHANISM / CONFORMATIONAL ANALYSIS / CONFORMATIONAL ENERGIES / A VALUES / STRAIN IN RING SYSTEMS / STEREOELECTRONIC EFFECTS / 7 FUNCTIONAL GROUP SYNTHESIS FUNCTIONAL GROUP MANIPULATION / CARBOXYLIC ACIDS / ESTERS / AMIDES / ACID CHLORIDES / ALDEHYDES / KETONES / IMINES AND IMINE DERIVATIVES / ALCOHOLS / AMINES / ALKENES / ALKANES / 8 CARBON–CARBON BOND FORMATION BETWEEN CARBON NUCLEOPHILES AND CARBON ELECTROPHILES SYNTHETIC STRATEGY / NUCLEOPHILIC CARBON / ELECTROPHILIC CARBON / REACTIVITY MATCHING / GENERATION OF NUCLEOPHILIC CARBON REAGENTS / GENERATION OF ELECTROPHILIC CARBON REAGENTS / MATCHING NUCLEOPHILES WITH ELECTROPHILES / ENOLATES / ENOLATE REGIOISOMERS / DIASTEREOSELECTION IN ALDOL REACTIONS / ORGANOMETALLIC COMPOUNDS / NEUTRAL CARBON NUCLEOPHILES / C=C FORMATION / CYCLOPROPANATION REACTIONS / METAL-CATALYZED CARBON–CARBON BOND FORMATION / PD(0)-CATALYZED CARBON–CARBON BOND FORMATION / HECK REACTION / SUZUKI COUPLING / STILLE COUPLING / OLE?N METATHESIS / 9 CARBON–CARBON BOND FORMATION BY FREE-RADICAL REACTIONS FREE-RADICAL REACTIONS / FREE-RADICAL POLYMERIZATION / NONPOLYMERIZATION REACTIONS / FREE-RADICAL INITIATION / FREE-RADICAL CYCLIZATION / 10 PLANNING ORGANIC SYNTHESES RETROSYNTHETIC ANALYSIS / CARBON SKELETON SYNTHESIS / UMPOLUNG SYNTHONS / ACETYLIDE NUCLEOPHILES / RING CONSTRUCTION / ROBINSON ANNULATION / DIELS–ALDER REACTION / HOMO–LUMO INTERACTIONS / STEREOELECTRONIC FACTORS / 1,3-DIPOLAR CYCLOADDITIONS / 11 STRUCTURE DETERMINATION OF ORGANIC COMPOUNDS STRUCTURE DETERMINATION / CHROMATOGRAPHIC PURI?CATION / INSTRUMENTAL METHODS / NUCLEAR MAGNETIC RESONANCE / CHEMICAL SHIFT / SPIN–SPIN COUPLING / DESCRIPTIONS OF SPIN SYSTEMS / SECOND-ORDER SPLITTING / STRUCTURE IDENTI?CATION BY 1H NMR / CARBON-13 NMR / INFRARED SPECTROSCOPY / IR STRETCHING FREQUENCIES / USE OF IR SPECTROSCOPY FOR STRUCTURE DETERMINATION / MASS SPECTROMETRY / FRAGMENTATION PROCESSES / SOLUTIONS TO CHAPTER PROBLEMS