Experimental organic chemistry Book

	Preface
	Introduction: Getting Acquainted with the Laboratory	1
Pt. 1	Experiments	13
1	Extraction of Caffeine from Tea	15
2	Purification and Thin-Layer Chromatographic Analysis of Caffeine	22
3	Synthesis of Ethanol by Fermentation of Sucrose	27
4	Synthesis of Salicylic Acid	32
5	Synthesis of Aspirin	41
	Optional Experiment: Thin-Layer Chromatographic Analysis of Analgesics	47
6	Radical Chlorination Reactions	49
7	Isolation of Essential Oils and the Theory of Odor	54
8	Nucleophilic Substitution Reactions	67
9	Addition Reactions of Alkenes	82
10	Dehydrohalogenation of 2-Bromoheptane: Variation of Promoting Base	103
11	Dehydration of Alcohols	108
12	Ether Syntheses	123
13	Grignard Syntheses	134
14	Phase Transfer Catalysis	160
15	Oxidation Reactions	171
16	Diels-Alder Reactions	188
17	Electrophilic Aromatic Substitution	201
18	Acylation and Alkylation of Aromatic Compounds	217
19	Reduction Reactions of 3-Nitroacetophenone	236
20	Photochemistry: Photoreduction of Benzophenone and Rearrangement to Benzpinacolone	244
21	Aldol Condensation: Reaction of Benzaldehyde and Acetone	252
22	Synthesis of 2,3,4,5-Tetraphenylcyclopentadienone	259
23	Horner-Emmons-Wittig Synthesis of Methyl 4-Methoxy-E-Cinnamate	267
24	Kinetic Versus Thermodynamic Control in Chemical Reactions	275
25	Synthesis of Esters	289
26	Amide Chemistry	305
27	Polyphosphoric Acid-Catalyzed Beckmann Rearrangement of Acetophenone Oxime	327
28	Synthesis of trans-1,2-Dibfnzocyclopropane by Ring Closure	333
29	Polymer Chemistry	339
Pt. 2	Projects	353
1	Hydrolysis of an Unknown Ester	355
2	Synthesis of 1-Bromobutane and a Grignard Synthesis of an Alcohol	369
3	Synthesis and Dehydration of 3,3-Dimethyl-2-Butanol	383
4	Interconversion of 4-tert-Butylcyclohexanol and 4-tert-Butylcyclohexanone	392
5	Aldol Condensation Using an Unknown Aldehyde and an Unknown Ketone: Derivative Formation and Identification of Unknowns	408
6	Benzoin Chemistry: Synthesis of an Anticonvulsant Drug Using Biochemical Catalysis	419
7	Synthesis of Benzocaine	435
8	Resolution of R,S-Benzoylamino Acids	443
9	Multistep Synthesis of Para Red from Acetanilide	456
10	Syntheses Starting with Alkyl Halides	467
11	Diels-Alder Cycloadditions of Various Dienophiles to 2,3-Dimethyl-1,3-Butadiene	471
12	Multistep Synthesis of N-Phenyltetraphenyl-Phthalimide	476
13	Sugars: The Glucose Pentaacetates	486
Pt. 3	Organic Qualitative Analysis	497
1	Identification of Unknowns	499
2	Physical Properties	502
3	Classification by Solubility and Elemental Analysis by Sodium Fusion	504
4	Infrared, Nuclear Magnetic Resonance, and Mass Spectrometric Analysis	516
5	Classification Tests for Functional Groups	524
6	Synthesis of Solid Derivatives	551
7	Separation of Mixtures	564
8	Summary of Identification Procedure for an Unknown Compound	572
9	Summary of Analysis of Mixture of Unknown Compounds	573
Pt. 4	Spectrometric Methods	577
1	Infrared Spectrometry	579
2	NMR Spectrometry	610
3	Mass Spectrometry	664
4	Ultraviolet and Visible Spectrometry	675
	Integrated Problems	683
Pt. 5	Techniques of the Organic Laboratory	687
1	Safety	689
2	Laboratory Glassware	706
3	Heating Methods	714
4	Extraction and Drying Agents	724
5	Recrystallization	749
6	Melting Points and Melting Ranges	765
7	Boiling Points, Distillation, and Azeotropes	776
8	Sublimation	805
9	Refractrometry	808
10	Thin-Layer Chromatography	813
11	Gas-Liquid Chromatography	826
12	Liquid Chromatography	841
13	Polarimetry	857
App. A	Derivative Tables for Organic Qualitative Analysis	A-1
App. B	The Literature of Organic Chemistry	B-1
	Index	I-1