Chemical resistance of common types of gloves to various
compounds
Glove type
Compound
Neoprene
Nitrile
Latex
Acetone
Chloroform
Dichloromethane
Diethyl ether
Ethanol
Ethyl acetate
Hexane
Methanol
Nitric acid (conc.)
Sodium hydroxide
Sulfuric acid (conc.)
Toluene
good
good
fair
very good
very good
good
excellent
very good
good
very good
good
fair
fair
poor
poor
good
excellent
poor
excellent
fair
poor
excellent
poor
fair
good
poor
poor
poor
excellent
fair
poor
fair
poor
excellent
poor
poor
Common organic solvents
Name
Boiling
Density
Dielectric Miscible
point (°C) (g · ml⫺1) constant with H2O
Acetone (2-propanone)
Dichloromethane
Diethyl ether
Ethanol (95% aq. azeotrope)
Ethanol (anhydrous)
Ethyl acetate
Hexane
Methanol
Pentane
2-Propanol (Isopropyl alcohol)
Toluene
56.5
40
35
78
78.5
77
69
65
36
82.5
111
0.792
1.326
0.713
0.816
0.789
0.902
0.660
0.792
0.626
0.785
0.866
21
9.1
4.3
27
25
6.0
1.9
33
1.8
18
2.4
yes
no
no
yes
yes
slightly
no
yes
no
yes
no
Selected data on common acid and base solutions
Compound
Molarity
Density
(g · ml⫺1)
% by weight
Acetic acid (glacial)
Ammonia (concentrated)
Hydrobromic acid (concentrated)
Hydrochloric acid (concentrated)
Nitric acid (concentrated)
Phosphoric acid (concentrated)
Sodium hydroxide
Sulfuric acid (concentrated)
17
15.3
8.9
12
16
14.7
6
18
1.05
0.90
1.49
1.18
1.42
1.70
1.22
1.84
100
28.4
48
37
71
85
20
95–98
Quick reference for other important tables
Page
13
C DEPT signals (22.8)
C chemical shifts (22.1)
Common GC stationary phases (19.1)
Drying agents (12.1)
Filter paper types (10.1)
1
H chemical shifts (21.2)
1
H coupling constants (21.6)
NMR Solvents, deuterated (21.1)
Recrystallization solvents (15.1)
TLC solvent polarities (17.1)
13
392
377
261
133
104
329
351
320
185
232
2.0 mL
1.5 mL
1.0 mL
Quick reference for other important figures
Page
Distillation
fractional (13.17)
simple (13.7)
short-path (13.8)
standard taper microscale (13.10)
Williamson microscale (13.13)
Extraction
microscale (11.8, 11.10)
miniscale (11.5)
Filtration, vacuum
microscale (10.7)
miniscale (10.6)
Glassware
standard taper miniscale (4.4)
standard taper microscale (4.6)
Williamson microscale (4.8)
160
149
152
153
156
0.5 mL
128, 130
123–124
111
110
33
35
36
0.1 mL
Quick reference for sections on sources of
confusion
Page
Computational chemistry
Distillation
Drying organic liquids
Extraction
Filtration
Gas chromatography (GC)
IR spectroscopy
Liquid chromatography (LC)
Melting points
Mass spectrometry (MS)
1
H NMR spectroscopy
Recrystallization
Thin-layer chromatography (TLC)
UV/VIS spectroscopy
cm
1
2
3
4
82
172
140
131
112
268
307
251
181
424
352
195
233
438
5
6
7
8
9
10
11
12
13
14
15
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Techniques
in Organic Chemistry
Publisher: Clancy Marshall
Sponsoring Editor: Kathryn Treadway
Assistant Editor: Tony Petrites
Editorial Assistant: Kristina Treadway
Director of Marketing: John Britch
Media and Supplements Editor: Dave Quinn
Project Editor: Leigh Renhard
Production Manager: Julia DeRosa
Design Manager: Blake Logan
Cover Designer: Michael Jung
Text Designer: Marcia Cohen
Illustration Coordinator: Bill Page
Illustrations: Fine Line Illustrations, Network Graphics
Composition: MPS Limited, A Macmillan Company
Printing and Binding: Quebecor Dubuque
Library of Congress Control Number: 2009934363
ISBN-13: 978-1-4292-1956-3
ISBN-10: 1-4292-1956-4
© 2010 by W. H. Freeman and Company
All rights reserved
Printed in the United States of America
First printing
W. H. Freeman and Company
41 Madison Avenue, New York, NY 10010
Houndmills, Basingstoke, RG21 6XS, England
www.whfreeman.com
This page intentionally left blank
Techniques
in Organic Chemistry
Miniscale, Standard Taper Microscale,
and Williamson Microscale
Third Edition
JERRY R. MOHRIG
Carleton College
CHRISTINA NORING HAMMOND
Vassar College
PAUL F. SCHATZ
University of Wisconsin, Madison
W. H. Freeman and Company
New York
Contents
Preface
xiii
PART 1 INTRODUCTION TO THE ORGANIC LABORATORY
1
ESSAY— The Role of the Laboratory
1
Safety in the Laboratory
3
1.1
1.2
1.3
1.4
1.5
1.6
2
Protecting the Environment
2.1
2.2
2.3
2.4
3
Causes of Laboratory Accidents / 3
Safety Features in the Laboratory / 5
Preventing Accidents / 6
What to Do if an Accident Occurs / 9
Chemical Toxicology / 10
Where to Find Chemical Safety Information / 11
Green Chemistry / 14
How Can a Laboratory Procedure Be Made Greener? / 15
Fewer Reaction By-Products / 18
Handling Laboratory Waste / 20
Laboratory Notebooks and Prelaboratory Information
3.1
3.2
3.3
14
21
The Laboratory Notebook / 21
Calculation of the Percent Yield / 24
Sources of Prelaboratory Information / 25
PART 2 CARRYING OUT CHEMICAL REACTIONS
4
ESSAY— Learning to Do Organic Chemistry
29
Laboratory Glassware
31
4.1
4.2
4.3
4.4
Desk Equipment / 31
Standard Taper Miniscale Glassware / 31
Microscale Glassware / 34
Cleaning and Drying Laboratory Glassware / 37
viii
5
Contents
Measurements and Transferring Reagents
5.1
5.2
5.3
5.4
6
7
8.4
8.5
9
9.5
67
Picturing Molecules on the Computer / 68
Molecular Mechanics Method / 69
Quantum Mechanics Methods: Ab Initio, Semiempirical,
and DFT Methods / 75
Which Computational Method Is Best? / 81
Sources of Confusion / 82
Designing a Chemical Reaction
9.1
9.2
9.3
9.4
58
Refluxing a Reaction Mixture / 59
Anhydrous Reaction Conditions / 61
Addition of Reagents During a Reaction / 62
Removal of Noxious Vapors / 63
Computational Chemistry
8.1
8.2
8.3
49
Preventing Bumping of Liquids / 50
Heating Devices / 51
Cooling Methods / 57
Laboratory Jacks / 58
Assembling a Reaction Apparatus
7.1
7.2
7.3
7.4
8
Using Electronic Balances / 38
Transferring Solids to a Reaction Vessel / 40
Measuring Volume and Transferring Liquids / 42
Measuring Temperature / 47
Heating and Cooling Methods
6.1
6.2
6.3
6.4
38
85
Importance of the Library / 86
Modifying the Scale of a Reaction and Carrying It Out / 86
Case Study: Synthesis of a Solvatochromic Dye / 90
Case Study: Oxidation of a Secondary Alcohol to a Ketone
Using NaOCl Bleach / 92
The Literature of Organic Chemistry / 93
PART 3 SEPARATION AND PURIFICATION TECHNIQUES
10
ESSAY— Intermolecular Forces in Organic Chemistry
Filtration
10.1
10.2
10.3
10.4
10.5
10.6
Filtering Media / 104
Miniscale Gravity Filtration / 106
Microscale Gravity Filtration / 108
Vacuum Filtration / 109
Other Liquid-Solid and Liquid-Liquid Separation Techniques / 112
Sources of Confusion / 112
99
104