Operational Organic Chemistry: A Problem-Solving Approach to the Laboratory Course

by Lehman, John W.

• ISBN13: 9780138419172
• ISBN10: 0138419175
• Edition: 3rd
• Format: Hardcover
• Copyright: 1999-01-01
• Publisher: Pearson College Div

Summary

This traditional-scale lab book prepares readers to perform the fundamental operations of organic chemistry in the laboratory and apply the operations intelligently in new situations -- to think and act like an organic chemist. Features traditional-scale laboratory procedures which do not require expensive, special glassware and which provide enough material for visual and physical characterization. Contains 115 experiments -- 12 experiments that teach basic operations, 46 experiments that reinforce concepts, and 47 minilabs (shorter experiments that can be used to fill partial or shorter lab periods). Features many experiments that use common or household compounds. Provides a section on qualitative organic analysis. Includes sections on using the chemical literature, keeping a notebook, and planning a synthesis. For anyone interested in organic chemistry.

Table of Contents

Preface	vi
To the Instructor	vii
Introduction	1	(18)
Laboratory Safety	9	(10)
Part I Mastering The Operations	19	(82)
1 Learning Basic Operations. The Effect of pH on a Food Preservative	20	(7)
2 Extraction and Evaporation. Separating the Components of "Panacetin"	27	(6)
3 Recrystallization and Melting-Point Measurement. Identifying a Component of "Panacetin"	33	(5)
4 Heating under Reflux. Synthesis of Salicylic Acid from Wintergreen Oil	38	(8)
5 Simple Distillation, Gas Chromatography. Preparation of Synthetic Banana Oil	46	(8)
6 Fractional Distillation. Separation of Petroleum Hydrocarbons	54	(6)
7 Addition, Mixing, Sublimation. Preparation of Camphor	60	(7)
8 Boiling Point, Refractive Index. Identification of a Petroleum Hydrocarbon	67	(7)
9 Column Chromatography, UV-VIS Spectrometry. Isolation and Isomerization of Lycopene from Tomato Paste	74	(7)
10 Steam Distillation, Infrared Spectrometry. Isolation and Identification of the Major Constituent of Clove Oil	81	(7)
11 Thin-Layer Chromatography, NMR Spectrometry. Identification of Unknown Ketones	88	(7)
12 Vacuum Distillation, Optical Rotation. Optical Activity of Alpha-Pinene	95	(6)
Part II Correlated Laboratory Experiments	101	(372)
13 Investigation of a Chemical Bond by Infrared Spectrometry	102	(7)
14 Properties of Common Functional Groups	109	(8)
15 Thin-Layer Chromatographic Analysis of Drug Components	117	(6)
16 Separation of an Alkane Clathrate	123	(7)
17 Isomers and Isomerization Reactions	130	(6)
18 Structures and Properties of Stereoisomers	136	(7)
19 Bridgehead Reactivity in an S(N)1 Solvolysis Reaction	143	(7)
20 Reaction of Iodoethane with Sodium Saccharin, an Ambident Nucleophile	150	(6)
21 Dehydration of Methylcyclohexanols	156	(10)
22 Synthesis of 7,7-Dichloronorcarane Using a Phase-Transfer Catalyst	166	(9)
23 Stereochemistry of the Addition of Bromine to trans-Cinnamic Acid	175	(7)
24 Hydration of a Difunctional Alkyne	182	(8)
25 Preparation of Bromotriphenylmethane and the Trityl Free Radical	190	(7)
26 Chain-Growth Polymerization of Styrene and Methyl Methacrylate	197	(9)
27 Synthesis of Ethanol by Fermentation	206	(8)
28 The Reaction of Butanols with Hydrobromic Acid	214	(9)
29 Borohydride Reduction of Vanillin to Vanillyl Alcohol	223	(9)
30 Multistep Synthesis of Cyclopentanol from Cyclohexanol	232	(10)
31 Synthesis of Triphenylmethanol and the Trityl Carbocation	242	(10)
32 Identification of a Conjugated Diene from Eucalyptus Oil	252	(7)
33 Spectral Identification of Terpenoids	259	(7)
34 Synthesis and Spectral Analysis of Aspirin	266	(8)
35 Preparation of Nonbenzenoid Aromatic Compounds	274	(10)
36 Mechanism of the Nitration of Arenes by Nitronium Fluoborate	284	(8)
37 Friedel-Crafts Acylation of Anisole	292	(9)
38 Structure of a Natural Product in Anise Oil	301	(7)
39 Identification of an Oxygen-Containing Organic Compound	308	(7)
40 Wittig Synthesis of 1,4-Diphenyl-1,3-Butadiene	315	(8)
41 Effect of Reaction Conditions on the Condensation of Furfural with Cyclopentanone	323	(8)
42 Haloform Oxidation of 4-Methoxyacetophenone	331	(7)
43 Electronic Effect of a para-Iodo Substituent	338	(9)
44 Synthesis and Identification of an Unknown Carboxylic Acid	347	(6)
45 Preparation of the Insect Repellent N,N-Diethyl-m-Toluamide	353	(11)
46 Synthesis of 2-Acetylcyclohexanone by the Stork Enamine Reaction	364	(9)
47 Synthesis of Dimedone and Measurement of Its Tautomeric Equilibrium Constant	373	(8)
48 Preparation of Para Red and Related Azo Dyes	381	(9)
49 Reaction of Phthalimide with Sodium Hypochlorite	390	(9)
50 Identification of an Unknown Amine	399	(8)
51 Preparation and Mass Spectrum of 2-Phenyl-indole	407	(9)
52 Nucleophilic Strength and Reactivity in S(N)Ar Reactions	416	(7)
53 Structure of an Unknown D-Hexose	423	(9)
54 Fatty Acid Content of Commercial Cooking Oils	432	(8)
55 Structure of an Unknown Dipeptide	440	(9)
56 Multistep Synthesis of Benzilic Acid from Benzaldehyde	449	(8)
57 Using the Chemical Literature in an Organic Synthesis	457	(7)
58 A Research Project in Organic Chemistry	464	(9)
Part III Minilabs	473	(56)
1 Making Useful Laboratory Items	474	(1)
2 Extraction of Iodine by Dichloromethane	475	(1)
3 Purification of an Unknown Compound by Recrystallization	476	(1)
4 Developing and Testing a Hypothesis	476	(2)
5 Preparation of Acetate Esters	478	(1)
6 Gas Chromatographic Analysis of Commercial Xylene	479	(1)
7 Isolation of Caffeine from No-Doz Tablets	480	(1)
8 A Missing Label Puzzle	480	(1)
9 Paper Chromatography of Dyes in Commercial Drink Mixes	481	(2)
10 Gas Chromatographic Analysis of an Essential Oil from Orange Peel	483	(1)
11 Identification of an Unknown Felt Tip Pen Ink by TLC	484	(1)
12 Optical Rotation of Turpentine	485	(1)
13 The Structures of Organic Molecules	486	(1)
14 Who Else Has My Compound?	487	(1)
15 Isomers and Molecular Structure	488	(2)
16 Reactivities of Alkyl Halides in Nucleophilic Substitution Reactions	490	(1)
17 An S(N)1 Reaction of Bromotriphenylmethane	491	(1)
18 Preparation and Properties of a Gaseous Alkene	492	(2)
19 The Addition of Iodine to Alpha-Pinene	494	(1)
20 Unsaturation in Commercial Products	495	(2)
21 Free-Radical Bromination of Hydrocarbons	497	(1)
22 The Nylon Rope Trick	498	(1)
23 Nucleophilic Substitution Rates of Alcohols	499	(1)
24 Photoreduction of Benzophenone to Benzopinacol	500	(2)
25 Oxidation of Alcohols by Potassium Perman-ganate	502	(1)
26 Preparation of a Fluorescent Dye	503	(1)
27 Diels-Alder Reaction of Maleic Anhydride and Furan	504	(2)
28 Identification of an Unknown Arene by NMR Spectrometry	506	(1)
29 Interpretation of a Mass Spectrum	507	(1)
30 Nitration of Naphthalene	508	(1)
31 Preparation of Trityl Cations by the Friedel-Crafts Reaction	509	(1)
32 Air Oxidation of Fluorene to 9-Fluorenone	510	(1)
33 A Nucleophilic Addition-Elimination Reaction of Benzil	511	(2)
34 Preparation of Aldol Condensation Products	513	(1)
35 A Spontaneous Reaction of Benzaldehyde	514	(1)
36 Acid/Base Strengths of Organic Compounds	515	(2)
37 Hydrolysis Rates of Esters	517	(1)
38 Preparation of Benzamide	518	(1)
39 Synthesis of Dimedone Derivatives of Benzal-dehyde	519	(1)
40 A Diazonium Salt Reaction of 2-Aminobenzoic Acid	520	(1)
41 Beckmann Rearrangement of Benzophenone Oxime	521	(1)
42 Dyeing with Indigo	522	(1)
43 Reactions of Monosaccharides with Phenols	523	(3)
44 Extraction of Trimyristin from Nutmeg	526	(1)
45 Preparation of a Soap Using a Phase-Transfer Catalyst	526	(1)
46 Isolation of a Protein from Milk	527	(2)
Part IV Qualitative Organic Analysis	529	(44)
An Overview of Qual Organic	530	(1)
Preliminary Work	531	(2)
Purification	531	(1)
Measurement of Physical Constants	531	(1)
Physical Examination	532	(1)
Ignition Test	532	(1)
Classification	533	(19)
Solubility Tests	533	(3)
Classification Tests	536	(16)
Spectral Analysis	552	(1)
Infrared Spectra	552	(1)
NMR Spectra	552	(1)
Identification	553	(18)
List of Possibilities	553	(1)
Additional Tests and Data	554	(1)
Preparation of Derivatives	554	(17)
Exercises	571	(2)
Part V The Operations	573	(189)
A Basic Operations	574	(10)
1 Cleaning and Drying Glassware	574	(1)
2 Using Standard-Taper Glassware	575	(2)
3 Using Glass Rod and Tubing	577	(2)
4 Weighing	579	(2)
5 Measuring Volume	581	(3)
B Operations for Conducting Chemical Reactions	584	(14)
6 Heating	584	(8)
7 Cooling	592	(1)
8 Temperature Monitoring	593	(1)
9 Mixing	594	(1)
10 Addition of Reactants	595	(3)
C Separation Operations	598	(37)
11 Gravity Filtration	598	(2)
12 Vacuum Filtration	600	(2)
13 Extraction	602	(6)
14 Evaporation	608	(3)
15 Steam Distillation	611	(5)
16 Column Chromatography	616	(9)
17 Thin-Layer Chromatography	625	(6)
18 Paper Chromatography	631	(4)
D Washing and Drying Operations	635	(9)
19 Washing Liquids	635	(1)
20 Drying Liquids	636	(4)
21 Drying Solids	640	(2)
22 Drying and Trapping Gases	642	(2)
E Purification Operations	644	(36)
23 Recrystallization	644	(9)
24 Sublimation	653	(3)
25 Simple Distillation	656	(9)
26 Vacuum Distillation	665	(6)
27 Fractional Distillation	671	(9)
F Measuring Physical Constants	680	(17)
28 Melting Point	680	(7)
29 Boiling Point	687	(3)
30 Refractive Index	690	(3)
31 Optical Rotation	693	(4)
G Instrumental Analysis	697	(65)
32 Gas Chromatography	697	(9)
33 High Performance Liquid Chromatography	706	(4)
34 Infrared Spectrometry	710	(23)
35 Nuclear Magnetic Resonance Spectrometry	733	(15)
36 Ultraviolet-Visible Spectrometry	748	(5)
37 Mass Spectrometry	753	(9)
Appendixes and Bibliography	762	(40)
I Laboratory Equipment	763	(2)
II Keeping a Laboratory Notebook	765	(1)
III Writing a Laboratory Report	766	(5)
IV Calculations for Organic Synthesis	771	(2)
V Planning an Experiment	773	(2)
VI Properties of Organic Compounds	775	(10)
VII The Chemical Literature	785	(13)
Bibliography	798	(4)
Index	802