This laboratory manual for organic chemistry courses provides an investigative approach for doing hands-on experimental work. It has been class-tested and fine-tuned for six years. It comprises largely non-traditional experiments that are designed to be covered in one three-hour laboratory period.
1 Safety in the Laboratory
2 Introduction
3 Melting Points
4 Crystallization
5 Distillation
6 Gas Chromatography
7 Thin-Layer Chromatography
8 Extraction: Separation of an Unknown Mixture
9 An Introuction to Stereochemistry: Use of Molecular Models
10 Infared Spectroscopy
11 Nuclear Magnetic Resonance Spectroscopy
12 Assignment of Structure by IR and 1H-NMR Spectroscopy
13 Preparative Scale GLC. Separation of Carvone and Limonene from Caroway Seed Oil
14 SN1 and SN2 Reactions
15 E2 Elimination Reactions, Dehydrobromination of the Byutyl Bromides, C4H9Br
16 Elimination Reaction, Dehydration of Butyl Alcohols
17 Hydroboration-Oxidation of Alkenes
18 Reduction of Ketones to Alcohols with Sodium Borohydride
19 Stereospecific Bromination of cis- and trans-Stilbene
20 Diphenylacetylene and (E)-1,2-Dibromostilbene
21 Addition Polymerization
22 The Diels-Alder Reaction
23 Aromatic Substitution I: Bromination of Aniline, Acetanilide, and Phenol
24 Aromatic Substitution II: Nitration of Methyl Benzoate: Relative Reactivity of Aromatic Compounds: A Competitive Nitration
25 The Grignard Reaction: The Synthesis of Triphenylmethanol
26 Chromic Acid Oxidation of Para-Nitrotoluene to Para-Nitrobenzoic Acid
27 Oxidation of Alcohols by a Chromate-Impregnated Resin: Following a Reaction by TLC
28 The Haloform Reaction. Oxidation of Aryl Methyl Ketones to Aromatic Carboxylic Acids
29 Synthesis of Isopentyl Acetate by Fischer Esterification
30 Acetylation: Aspirin and N-Acetylanthranilic Acid
31 Preparation of a Liquid Crystal: The Enol Acetate of 4-Cholestene-3-one
32 The Claisen-Schmidt Reaction: Benzalacetone and Dibenzalacetone
33 Aryldiazonium Ion Reactions: Formation, Displacement, Coupling
34 Dyes Produced by Diazo Coupling and Diazo Imaging
35 Imaging Dyes in Color Photography
36 Qualitative Organic Analysis. Part 1: Preliminary Measurements and Classification Tests
37 Qualitative Organic Analysis. Part 2: Prepartion of Derivatives and Final Identification
38 Tables of Physical Properties of Compounds and their Derivatives
Appendix