THE PRINCIPLES OF ORGANIC CHEMISTRY
PART 1: THEORY AND TECHNIQUES CHAPTER 1: SAFETY IN THE CHEMISTRY LABORATORY 11 PERSONAL SATEY 12 FIRE/EARTHQUAKE/EMERGENCY EVACUATION 13 EQUIPMENT SAFETY 14 CHEMICAL SAFETY 15 CLEANUP AND WASTE DISPOSAL CHAPTER 2: THE LABORATORY NOTEBOOK AND THE LABORATORY PERIOD 21 BEFORE THE LABORATORY PERID 22 DURING THE LABORATORY PERIOD 23 BEFORE LEAVING THE LAB 24 AFTER THE LABORATORY PERIOD 25 YOUR RESPONSIBILITY AT ALL TIMES CHAPTER 3: WHERE TO FIND IT: SEARCHING THE LITERATURE CHAPTER 4: THINGS YOU NEED TO KNOW BEFORE YOU BEGIN 41 ACID-BASE REACTIONS 42 LIMITING RESCTIONS, THEORETICAL YIELD AND PRECENT YIELD CHAPTER 5: PROPERTIES OF ORGANIC MOLECULES 51 BONDING BETWEEN ATOMS TO FORM MOLECULES 52 THE EFFECT OF STRUCTURE ON THE POLARITY OF MOLECULES 53 THE TYPES OF INTERMOLECULAR FORCES 54 INTERMOLECULAR FORCES BETWEEN DISSIMILAR MOLECULES 55 THE DISTINCTION BETWEEN SOLUBILITY AND REACTIVITY 56 PROBLEMS CHAPTER 6: CHARACTERISTIC PHYSICAL PROPERTIES OF PURE COMPOUNDS 61 SOLUBILITY 62 CHANGES IN PHYSICAL STATE 63 MELTING POINT RANGE 64 BOILING POINT 65 SUBLIMATION CHAPTER 7: ISOLATION AND PURIFICATION OF COMPOUNDS 71 RECRYSTALLIZATION 72 FILTRATION 73 DISTILLATION 74 REFLUX 75 SUBLIMATION/EVAPORATION 76 EXTRACTION AND WASHING 77 DRYING 78 CHROMATOGRAPHY CHAPTER 8: STRUCTURE DETERMINATION 81 NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY 82 MASS SPECTROMETRY 83 INFRARED SPECTROSCOPY CHAPTER 9: RUNNING A SYNTHETIC REACTION 91 REPRODUCING A PUBLISHED SYNTHESIS 92 RUNNING A NEW SYNTHETIC REACTION PART 2: EXPERIMENTS EXPERIMENT 1: CALIBRATING A PASTEUR PIPETTE EXPERIMENT 2: INVESTIGATING SOLUBILITY AND ACID-BASE REACTIONS EXPERIMENT 3: MIXED MELTING POINTS EXPERIMENT 4: WHITTLING DOWN THE POSSIBILITIES: IDENTIFYING AN UNKNOWN USING MOLECULAR DIPOLE MOMENT, SOLUBILITY, DENSITY, AND BOILING POINT DATA EXPERIMENT 5: RECRYSTALLIZATION AND MELTING POINTS: RECRYSTALLIZATION OF ADIPIC AND SALICYLIC ACIDS EXPERIMENT 6: RECRYSTALLIZATION AND MELTING POINTS: RECRYSTALLIZATION OF AN UNKNOWN SOLID AND DECOLORIZATION OF BROWN SUGAR EXPERIMENT 7: THIN LAYER CHROMATOGRAPHY (TLC) EXPERIMENT 8: IDENTIFICATION OF AN ADULTERATED HERB OR SPICE BY THIN LAYER CHROMATOGRAPHY (TLC) EXPERIMENT 9: WHAT DO YOU TAKE FOR PAIN? EXPERIMENT 10: NUCLEOPHILIC SUBSTITUTION REACTIONS OF ALKYL HALIDES EXPERIMENT 11: ISOLATION OF TRIMYRISTIN FROM NUTMEG EXPERIMENT 12: THE MAGTRIEVE™ OXIDATION OF 4-CHLOROBENZYL ALCOHOL, A SOLVENT-FREE REACTION EXPERIMENT 13: THE SODIUM BOROHYDRIDE REDUCTION OF BENZIL AND BENZOIN EXPERIMENT 14: THE GRIGNARD REACTION: THE PREPARATION OF 1,1-DIPHENYLETHANOL EXPERIMENT 15: THE ASYMMETRIC DIHYDROXYLATION OF TRANS-STILBENE EXPERIMENT 16: SOME CHEMISTRY OF ?-PINENE OXIDE EXPERIMENT 17: A DEHYDROGENATION/ HYDROGENATION REACTION EXPERIMENT 18: THE FRIEDEL-CRAFTS REACTION EXPERIMENT 19: MICROWAVE HEATING OF ORGANIC COMPOUNDS EXPERIMENT 20: THE REACTION OF 1,1-DIPHENYLETHANOL ON CLAY IN THE PRESENCE OF MICROWAVE RADIATION EXPERIMENT 21: THE WITTIG REACTION EXPERIMENT 22: THE SUZUKI REACTION EXPERIMENT 23: THE CROSSED-ALDOL CONDENSATION EXPERIMENT 24: IDENTIFYING THE STRUCTURE OF AN ALDEHYDE BY QUALITATIVE ANALYSIS EXPERIMENT 25: THE BENZOIN REACTION EXPERIMENT 26: THE DIELS-ALDER REACTION EXPERIMENT 27: SYNTHESIS OF AN ?,?-UNSATURATED CARBOXYLIC ACID DERIVATIVE EXPERIMENT 28: THE REACTION OF 2-ACETYLPHENYL BENZOATE WITH POTASSIUM HYDROXIDE PART I EXPERIMENT 29: THE REACTION OF 2-ACETYLPHENYL BENZOATE WITH POTASSIUM HYDROXIDE PART II EXPERIMENT 30: SYNTHESIS OF 1,2,3,4-TETRAHYDRO-?-CARBOLINE EXPERIMENT 31: BASE-CATALYZED HYDROLYSIS OF NICOTINONITRILE USING AN ANION-EXCHANGE RESIN EXPERIMENT 32: REACTIONS OF SALICYLAMIDE EXPERIMENT 33: THE HUNSDIECKER REACTION EXPERIMENT 34: THE INVESTIGATION OF THE MECHANISM OF A REACTION EXPERIMENT 35: MONOTERPENES AND THE RITTER REACTION EXPERIMENT 36: CHEMOSELECTIVITY IN TRANSFER-HYDROGENATION REACTIONS