9780716728184

Experimental Organic Chemistry: A Balanced Approach : Macroscale and Microscale

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  • ISBN13:

    9780716728184

  • ISBN10:

    0716728184

  • Format: Hardcover
  • Copyright: 1997-08-01
  • Publisher: W H Freeman & Co
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Table of Contents

PREFACE xx
INTRODUCTION: GETTING ACQUAINTED WITH THE LABORATORY 1(12)
I.1 Experimental Organic Chemistry 1(1)
1.2 Laboratory Safety 1(1)
I.3 Cleanup Following an Experiment 2(1)
I.4 Desk Equipment 3(1)
I.5 Introduction to Macroscale and Microscale Laboratory Work 4(1)
I.6 Using Handbooks 5(4)
I.7 Your Laboratory Notebook 9(4)
Part 1 Experiments 13(340)
1 EXTRACTION OF CAFFEINE FROM TEA
15(7)
2 PURIFICATION AND THIN-LAYER CHROMATOGRAPHIC ANALYSIS OF CAFFEINE
22(5)
3 SYNTHESIS OF ETHANOL BY FERMENTATION OF SUCROSE
27(5)
4 SYNTHESIS OF SALICYLIC ACID
32(9)
5 SYNTHESIS OF ASPIRIN
41(8)
Optional Experiment: Thin-Layer Chromatographic Analysis of Analgesics
47(2)
6 RADICAL CHLORINATION REACTIONS
49(5)
7 ISOLATION OF ESSENTIAL OILS AND THE THEORY OF ODOR
54(13)
7.1 Isolation of S-(+)-Carvone from Caraway Seeds
56(7)
7.2 Isolation of R-(+)-Limonene from Orange Peels
63(4)
8 NUCLEOPHILIC SUBSTITUTION REACTIONS
67(15)
8.1 S(N)1/S(N)2 Reactivity of Alkyl Halides
71(5)
8.2 Preparation and Identification of Alkyl Bromides Synthesized from Unknown Alcohols
76(6)
9 ADDITION REACTIONS OF ALKENES
82(21)
9.1 Free Radical versus Ionic Addition of Hydrobromic Acid to Alkenes
83(8)
9.2 Dimerization of 2-Methylpropene (Isobutylene)
91(7)
9.3 Stereochemistry of Bromine Addition to trans-Cinnamic Acid
98(5)
10 DEHYDROHALOGENATION OF 2-BROMOHEPTANE: VARIATION OF PROMOTING BASE
103(5)
11 DEHYDRATION OF ALCOHOLS
108(15)
11.1 Synthesis of Cyclohexene by Acid-Catalyzed Dehydration of Cyclohexanol
110(6)
11.2 Dehydration of 2-Methylcyclohexanol
116(7)
12 ETHER SYNTHESES
123(11)
12.1 Williamson Ether Synthesis of Ethoxybutane
124(5)
12.2 Synthesis and Analysis of a Propyl Benzhydryl Ether
129(5)
13 GRIGNARD SYNTHESES
134(26)
13.1 Synthesis of Phenylmagnesium Bromide and Its Use as a Synthetic Intermediate
138(17)
13.1a Synthesis of Diphenylmethanol (Benzhydrol)
142(6)
13.1b Synthesis of Triphenylmethanol
148(3)
13.1c Synthesis of Benzoic Acid
151(4)
13.2 Grignard Synthesis of a Triphenylmethane Dye: Crystal Violet or Malachite Green
155(5)
14 PHASE TRANSFER CATALYSIS
160(11)
14.1 Williamson Ether Synthesis of Bis-4-Chlorobenzyl Ether Using Phase Transfer Catalysis
162(5)
14.2 Synthesis of Butyl Benzoate Using Phase Transfer Catalysis
167(4)
15 OXIDATION REACTIONS
171(17)
15.1 Oxidation of Cyclohexanol Using Sodium Hypochlorite
174(5)
15.2 General Method for Oxidizing Secondary Alcohols to Ketones
179(4)
15.3 Oxidation of Cinnamyl Alcohol Using Pyridinium Chlorochromate
183(5)
16 DIELS-ALDER REACTIONS
188(13)
16.1 Synthesis of Dimethyl 3,4,5,6-Tetraphenylphthalate from 2,3,4,5-Tetraphenylcyclopentadienone and Dimethyl Acetylene Dicarboxylate
189(5)
16.2 Synthesis of 4-Cyclohexene-cis-1,2-Dicarboxylic Acid from Butadiene Sulfone and Maleic Anhydride
194(7)
17 ELECTROPHILIC AROMATIC SUBSTITUTION
201(16)
17.1 Iodination of 1,2,4,5-Tetramethylbenzene Using Iodine and Periodic Acid
203(5)
17.2 Bromination of Acetanilide
208(6)
Optional Experiment: Removal of the Acetyl Protecting Group: Synthesis of a Bromoaniline
212(2)
17.3 Rates of Electrophilic Aromatic Substitution
214(3)
18 ACYLATION AND ALKYLATION OF AROMATIC COMPOUNDS
217(19)
18.1 Acylation of Ferrocene
220(6)
18.2 Synthesis of 4,4'-Di-tert-Butylbiphenyl
226(6)
18.3 Synthesis of 1,4-Di-tert-Butyl-2,5-Dimethoxybenzene
232(4)
19 REDUCTION REACTIONS OF 3-NITROACETOPHENONE
236(8)
19.1 Reduction of 3-Nitroacetophenone Using Tin and Hydrochloric Acid
239(2)
19.2 Reduction of 3-Nitroacetophenone Using Sodium Borohydride
241(3)
20 PHOTOCHEMISTRY: PHOTOREDUCTION OF BENZOPHENONE AND REARRANGEMENT TO BENZPINACOLONE
244(8)
21 ALDOL CONDENSATION: REACTION OF BENZALDEHYDE AND ACETONE
252(7)
22 SYNTHESIS OF 2,3,4,5-TETRAPHENYLCYCLOPENTADIENONE
259(8)
23 HORNER-EMMONS-WITTIG SYNTHESIS OF METHYL 4-METHOXY-E-CINNAMATE
267(8)
24 KINETIC VERSUS THERMODYNAMIC CONTROL IN CHEMICAL REACTIONS
275(14)
24.1 Semicarbazones of Cyclohexanone and 2-Furaldehyde
276(8)
24.2 Friedel-Crafts Alkylation of Chlorobenzene
284(5)
Optional Experiments
289(1)
25 SYNTHESIS OF ESTERS
289(16)
25.1 Synthesis of Isopentyl Acetate (Banana Oil)
291(6)
Optional Experiments: Propyl Ethanoate (Propyl Acetate) and 2-Methyl-1-Propyl Propanoate (Isobutyl Propionate)
296(1)
25.2 Synthesis and Identification of an Ester from an Unknown Alcohol and Acetic Acid
297(8)
26 AMIDE CHEMISTRY
305(22)
26.1 Synthesis of Hippuric Acid
306(7)
Optional Experiment: Solubilities of Benzoic Acid and Hippuric Acid
312(1)
26.2 Synthesis of a Mosquito Repellent: N,N-Diethyl-meta-Toluamide (Deet)
313(14)
27 POLYPHOSPHORIC ACID-CATALYZED BECKMANN REARRANGEMENT OF ACETOPHENONE OXIME
327(6)
28 SYNTHESIS OF trans-1,2-DIBENZOCYCLOPROPANE BY RING CLOSURE
333(6)
29 POLYMER CHEMISTRY
339(14)
29.1 Synthesis of Polystyrene
342(7)
Optional Experiment
348(1)
29.2 Biodegradable Starch Films
349(4)
Part 2 Projects 353(144)
1 HYDROLYSIS OF AN UNKNOWN ESTER
355(14)
1.1 Hydrolysis and Azeotropic Distillation
357(3)
1.2 Extraction and Recrystallization
360(4)
1.3 Distillation, Melting Points, and Identification
364(5)
2 SYNTHESIS OF 1-BROMOBUTANE AND A GRIGNARD SYNTHESIS OF AN ALCOHOL
369(14)
2.1 Synthesis of 1-Bromobutane from 1-Butanol
370(5)
Optional Syntheses of Alkyl Halides
374(1)
2.2 Grignard Synthesis of Secondary and Tertiary Alcohols
375(8)
Optional Synthesis
380(3)
3 SYNTHESIS AND DEHYDRATION OF 3,3-DIMETHYL-2-BUTANOL
383(9)
3.1 Synthesis of 3,3-Dimethyl-2-Butanol by Reduction with Sodium Borohydride
384(3)
3.2 Acid-Catalyzed Dehydration of 3,3-Dimethyl-2-Butanol with Rearrangement
387(5)
4 INTERCONVERSION OF 4-tert-BUTYLCYCLOHEXANOL AND 4-tert-BUTYLCYCLOHEXANONE
392(16)
4.1 Sodium Hypochlorite Oxidation of 4-tert-Butylcyclohexanol to 4-tert-Butylcyclohexanone
394(6)
4.2 Sodium Borohydride Reduction of 4-tert-Butylcyclohexanone
400(5)
Optional GC or NMR Experiment
405(3)
5 ALDOL CONDENSATION USING AN UNKNOWN ALDEHYDE AND AN UNKNOWN KETONE: DERIVATIVE FORMATION AND IDENTIFICATION OF UNKNOWNS
408(11)
5.1 Preparation of Aldol Condensation Product
413(1)
5.2 Characterization of the Aldol Product
414(5)
6 BENZOIN CHEMISTRY: SYNTHESIS OF AN ANTICONVULSANT DRUG USING BIOCHEMICAL CATALYSIS
419(16)
6.1 Thiamine-Catalyzed Benzoin Condensation
419(8)
6.2 Oxidation of Benzoin
427(4)
6.3 Synthesis of 5,5-Diphenylhydantoin, an Anticonvulsant Drug
431(4)
7 SYNTHESIS OF BENZOCAINE
435(8)
8 RESOLUTION OF R,S-BENZOYLAMINO ACIDS
443(13)
8.1 Papain
444(4)
8.2 Resolution of R,S-Benzoylamino Acids
448(1)
8.3 Synthesis of the R,S-Benzoylamino Acid
449(3)
8.4 Synthesis of the S-Benzoylamino Acid Anilide: Enzymatic Resolution
452(1)
8.5 Optical Activity of S-Benzoylamino Acid Anilide
453(2)
8.6 Further Experiment
455(1)
9 MULTISTEP SYNTHESIS OF PARA RED FROM ACETANILIDE
456(11)
9.1 Two-Step Synthesis of p-Nitroaniline
459(4)
9.2 Preparation of Diazonium Salts
463(4)
10 SYNTHESES STARTING WITH ALKYL HALIDES
467(4)
11 DIELS-ALDER CYCLOADDITIONS OF VARIOUS DIENOPHILES TO 2,3-DIMETHYL-1,3-BUTADIENE
471(5)
11.1 Synthesis of cis-4,5-Dimethyl-1,2,3,6-Tetrahydrophthalic Anhydride
471(2)
11.2 Addition of Various Dienophiles to 2,3-Dimethyl-1,3-Butadiene
473(3)
12 MULTISTEP SYNTHESIS OF N-PHENYLTETRAPHENYL-PHTHALIMIDE
476(10)
12.1 Synthesis of Tetraphenylcyclopentadienone
478(1)
12.2 Synthesis of Dimethyl Tetraphenylphthalate
479(1)
12.3 Synthesis of Tetraphenylphthalic Acid
480(2)
12.4 Synthesis of Tetraphenylphthalic Anhydride
482(2)
12.5 Synthesis of N-Phenyl-3,4,5,6-Tetraphenylphthalimide
484(2)
13 SUGARS: THE GLUCOSE PENTAACETATES
486(11)
13.1 Preparation of Stereoisomers of D-Glucose
491(2)
13.2 (1)H NMR Analysis of XXX- and XXX-D-Glucose Pentaacetates
493(1)
13.3 Optical Activity of Sugars
493(1)
13.4 Further Investigations
494(3)
Part 3 Organic Qualitative Analysis 497(80)
1 IDENTIFICATION OF UNKNOWNS
499(3)
2 PHYSICAL PROPERTIES
502(2)
3 CLASSIFICATION BY SOLUBILITY AND ELEMENTAL ANALYSIS BY SODIUM FUSION
504(12)
3.1 Classification by Solubility
504(8)
3.2 Elemental Analysis by Sodium Fusion
512(4)
4 INFRARED, NUCLEAR MAGNETIC RESONANCE, AND MASS SPECTROMETRIC ANALYSIS
516(8)
4.1 Using Spectrometric Data
520(4)
5 CLASSIFICATION TESTS FOR FUNCTIONAL GROUPS
524(27)
5.1 Alcohols
526(3)
5.2 Aldehydes and Ketones
529(4)
5.3 Alkenes
533(2)
5.4 Alkyl Halides
535(3)
5.5 Amines
538(3)
5.6 Aromatic Hydrocarbons (Arenes)
541(2)
5.7 Aryl Halides
543(1)
5.8 Carboxylic Acids
543(1)
5.9 Carboxylic Acid Derivatives
544(1)
5.9a Acyl Chlorides
544(1)
5.9b Esters
544(1)
5.10 Amides, Acyl Chlorides, Esters, and Nitriles
545(4)
5.11 Ethers
549(1)
5.12 Phenols
549(2)
6 SYNTHESIS OF SOLID DERIVATIVES
551(13)
6.1 Alcohols
552(3)
6.2 Aldehydes and Ketones
555(2)
6.3 Amines
557(3)
6.4 Carboxylic Acides: Amides, Anilides, Toluidides
560(2)
6.5 Phenols
562(2)
7 SEPARATION OF MIXTURES
564(8)
7.1 Assaying the Number of Compounds
567(1)
7.2 Separating the Mixture
568(3)
7.3 Model Extraction Procedure
571(1)
8 SUMMARY OF IDENTIFICATION PROCEDURE FOR AN UNKNOWN COMPOUND
572(1)
9 SUMMARY OF ANALYSIS OF A MIXTURE OF UNKNOWN COMPOUNDS
573(4)
Part 4 Spectrometric Methods 577(110)
1 INFRARED SPECTROMETRY
579(31)
1.1 Theory of Molecular Vibration
580(1)
1.2 Infrared Spectrum
581(3)
1.3 Infrared Instrumentation
584(4)
1.4 Techniques of Sample Preparation
588(5)
1.5 Interpreting Infrared Spectra
593(17)
2 NMR SPECTROMETRY
610(54)
2.1 NMR Instrumentation
612(2)
2.2 Chemical Shift
614(7)
2.3 Spin-Spin Splitting
621(3)
2.4 Detecting Chemical Equivalence
624(2)
2.5 Integration
626(1)
2.6 Preparing the NMR Sample
627(3)
2.7 Recording the NMR Spectrum
630(1)
2.8 Interpreting (1)H NMR Spectra
630(4)
2.9 (13)C NMR
634(6)
2.10 An Approach to Solving NMR Problems
640(10)
2.11 Two-Dimensional NMR and Related Techniques (Special Topic)
650(14)
3 MASS SPECTROMETRY
664(11)
4 ULTRAVIOLET AND VISIBLE SPECTROMETRY
675(8)
5 INTEGRATED PROBLEMS
683(4)
Part 5 Techniques of the Organic Laboratory 687
1 SAFETY
689(17)
1.1 Causes of Laboratory Accidents
689(3)
1.2 Safety Features of Your Laboratory
692(2)
1.3 Preventing Accidents
694(2)
1.4 What to Do if an Accident Occurs
696(1)
1.5 Chemical Toxicology
697(1)
1.6 Where to Find Chemical Safety Information
698(5)
1.7 Protecting The Environment
703(3)
2 LABORATORY GLASSWARE
706(8)
2.1 Standard Taper Glassware
706(4)
2.2 Microscale Glassware
710(1)
2.3 Cleaning Your Glassware
711(1)
2.4 Pasteur Filter Pipets
712(2)
3 HEATING METHODS
714(10)
3.1 Boiling Stones
714(1)
3.2 Heating Devices
715(4)
3.3 Refluxing a Reaction Mixture
719(5)
3.3a Refluxing a Reaction Mixture under Anhydrous Conditions
720(4)
4 EXTRACTION AND DRYING AGENTS
724(25)
4.1 Extraction: The Theory
726(2)
4.2 Macroscale Extractions
728(2)
4.3 Additional Information about Extractions
730(4)
4.4 Summary of Macroscale Extraction from Water to an Organic Solution
734(1)
4.5 Microscale Extractions
734(8)
4.5a Extracting an Aqueous Solution with an Organic Solvent More Dense Than Water
736(1)
4.5b Washing an Organic Liquid That Is More Dense Than Water
737(4)
4.5c Extraction with an Organic Solvent Less Dense Than Water
741(1)
4.5d Washing an Organic Liquid That Is Less Dense Than Water
741(1)
4.6 Drying Organic Liquids
742(3)
4.7 Methods for Separating Drying Agents and Organic Liquids
745(1)
4.8 Recovery of the Organic Product from the Dried Extraction Solution
746(3)
5 RECRYSTALLIZATION
749(16)
5.1 Theory of Recrystallization
749(3)
5.2 Selecting a Proper Recrystallization Solvent
752(2)
5.2a Recrystallization from Mixed Solvent Pairs
753(1)
5.3 Macroscale Procedure for Recrystallizing a Solid
754(5)
5.3a Removing Impurities from the Recrystallization Solution
756(3)
5.4 Summary of the Macroscale Recrystallization Procedure
759(1)
5.5 Microscale Recrystallization
759(4)
5.5a Recrystallizing 150 to 500 Milligrams of a Solid
759(2)
5.5b Recrystallizing Less than 150 to 500 Milligrams of a Solid in a Craig Tube Apparatus
761(2)
5.6 Summary of the Microscale Recrystallization Procedures
763(1)
5.7 What to Do If No Crystals Appear in the Cooled Solution
763(1)
5.8 Pointers for Successful Recrystallizations
764(1)
6 MELTING POINTS AND MELTING RANGES
765(11)
6.1 Melting Point Theory
766(2)
6.2 Apparatus for Determining Melting Ranges
768(3)
6.3 Determining Melting Ranges
771(2)
6.4 Mixture Melting Points
773(1)
6.5 Thermometer Calibration
774(1)
6.6 Summary of Melting-Point Determination
775(1)
7 BOILING POINTS, DISTILLATION, AND AZEOTROPES
776(29)
7.1 Boiling Points
777(2)
7.1a Determination of Boiling Points
778(1)
7.2 Boiling Points and Separation of Mixtures
779(4)
7.3 Simple Distillation
783(8)
7.3a Short-Path Distillation
788(1)
7.3b Microscale Distillation
789(2)
7.4 Fractional Distillation
791(3)
7.5 Azeotropic Distillation
794(2)
7.6 Steam Distillation
796(2)
7.7 Vacuum Distillation
798(7)
8 SUBLIMATION
805(3)
8.1 Assembling the Apparatus for a Sublimation
806(1)
8.2 Carrying Out a Microscale Sublimation
807(1)
9 REFRACTROMETRY
808(5)
9.1 Theory of Refractometry
809(1)
9.2 The Refractometer
810(1)
9.3 Steps in Determining a Refractive Index
811(1)
9.4 Temperature Correction
812(1)
10 THIN-LAYER CHROMATOGRAPHY
813(13)
10.1 Principles of Thin-Layer Chromatography
815(2)
10.2 Plates for Thin-Layer Chromatography
817(1)
10.3 Sample Application
818(2)
10.4 Choices of Developing Solvent
820(3)
10.5 Visualization Techniques
823(2)
10.6 Summary of TLC Procedure
825(1)
11 GAS-LIQUID CHROMATOGRAPHY
826(15)
11.1 Instrumentation
827(2)
11.2 Columns and Liquid Stationary Phases
829(3)
11.3 Detectors
832(3)
11.4 Interpreting Chromatograms
835(1)
11.5 Practical GC Operating Procedures
836(3)
11.6 Identification of Components and Qualitative Analysis
839(2)
12 LIQUID CHROMATOGRAPHY
841(16)
12.1 Adsorbents
842(2)
12.2 Elution Solvents
844(1)
12.3 Choosing a Column
845(2)
12.4 Making a Macroscale Column
847(1)
12.5 Elution Techniques
848(2)
12.6 Microscale Column Chromatography
850(1)
12.7 Summary of Column Chromatography Techniques
851(1)
12.8 Dry Column Chromatography
852(1)
12.9 Flash Chromatography
852(2)
12.10 High-Performance Liquid Chromatography
854(3)
13 POLARIMETRY
857
13.1 Mixtures of Optical Isomers: Separation/Resolution
857(5)
13.2 Polarimetric Instrumentation
862(2)
13.3 Specific Rotation
864(2)
13.4 Using the Polarimeter
866(1)
13.5 Enantiomeric Excess (Optical Purity)
867
Appendix A DERIVATIVE TABLES FOR ORGANIC QUALITATIVE ANALYSIS A-1
Appendix B THE LITERATURE OF ORGANIC CHEMISTRY B-1
Index I-1

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