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Advanced Practical Organic Chemistry 3rd edition [Mīkstie vāki]

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(AstraZeneca, Macclesfield, UK)
  • Formāts: Paperback / softback, 356 pages, height x width: 234x156 mm, weight: 580 g, 20 Tables, black and white; 153 Illustrations, black and white
  • Izdošanas datums: 08-Jan-2013
  • Izdevniecība: CRC Press Inc
  • ISBN-10: 1439860971
  • ISBN-13: 9781439860977
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Advanced Practical Organic Chemistry 3rd editionPalielināt
  • Formāts: Paperback / softback, 356 pages, height x width: 234x156 mm, weight: 580 g, 20 Tables, black and white; 153 Illustrations, black and white
  • Izdošanas datums: 08-Jan-2013
  • Izdevniecība: CRC Press Inc
  • ISBN-10: 1439860971
  • ISBN-13: 9781439860977
Citas grāmatas par šo tēmu:
Speciālā piedāvājuma visas grāmatas: Taylor & Francis offers several science and technology titles with ISE (International Student Edition) prices
Permanent link: https://www.kriso.lv/db/9781439860977.html
Keywords:

Any research that uses new organic chemicals, or ones that are not commercially available, will at some time require the synthesis of such compounds. Therefore, organic synthesis is important in many areas of both applied and academic research, from chemistry to biology, biochemistry, and materials science. The third edition of a bestseller, Advanced Practical Organic Chemistry is a guide that explains the basic techniques of organic chemistry, presenting the necessary information for readers to carry out widely used modern organic synthesis reactions.

This book is written for advanced undergraduate and graduate students as well as industrial organic chemists, particularly those involved in pharmaceutical, agrochemical, and other areas of fine chemical research. It provides the novice or nonspecialist with the often difficult-to-find information on reagent properties needed to perform general techniques. With over 80 years combined experience training and developing organic research chemists in industry and academia, the authors offer sufficient guidance for researchers to perform reactions under conditions that give the highest chance of success, including the appropriate precautions to take and proper experimental protocols. The text also covers the following topics:

  • Record keeping and equipment
  • Solvent purification and reagent preparation
  • Using gases and working with vacuum pumps
  • Purification, including crystallization and distillation
  • Small-scale and large-scale reactions
  • Characterization, including NMR spectra, melting point and boiling point, and microanalysis
  • Efficient ways to find information in the chemical literature

With fully updated text and all newly drawn figures, the third edition provides a powerful tool for building the knowledge on the most up-to-date techniques commonly used in organic synthesis.

Recenzijas

Praise for Previous Editions

"concise and highly readable I would recommend this book as an essential purchase for all new research students in the area of organic synthesis" Synthesis, June 1995

"This book should be present in every organic chemistry research laboratorya bargain at the price." Chemistry & Industry, July 1995

"Reading this book is like having a thoughtful and smart tutor guiding all your steps in the laboratoryexcellent choice.." Physical Sciences Educational Reviews Praise for the Second Edition:" an essential purchase for all new research students in the area of organic synthesis." Synthesis

"This book should be present in every organic chemistry research laboratory"

Chemistry & Industry

"Reading this book is like having a thoughtful and smart tutor guiding all your steps in the laboratory excellent choice." Physical Sciences Educational Reviews

List of Figures
xiii
List of Tables
xxi
Preface xxiii
Authors xxv
Chapter 1 General introduction
1(2)
Chapter 2 Safety
3(10)
2.1 Safety is your primary responsibility
3(1)
2.2 Safe working practice
4(1)
2.3 Safety risk assessments
4(1)
2.4 Common hazards
5(5)
2.4.1 Injuries caused by use of laboratory equipment and apparatus
5(1)
2.4.2 Toxicological and other hazards caused by chemical exposure
5(1)
2.4.3 Chemical explosion and fire hazards
6(4)
2.5 Accident and emergency procedures
10(1)
Bibliography
10(3)
Chapter 3 Keeping records of laboratory work
13(28)
3.1 Introduction
13(1)
3.2 The laboratory notebook
13(8)
3.2.1 Why keep a lab book?
13(1)
3.2.2 Laboratory records, experimental validity and intellectual property
14(1)
3.2.3 How to write a lab book: Paper or electronic
15(2)
3.2.4 Paper lab notebook: Suggested lab notebook format
17(3)
3.2.5 Electronic laboratory notebooks
20(1)
3.3 Keeping records of data
21(8)
3.3.1 Purity, structure determination, and characterization
22(1)
3.3.2 What types of data should be collected?
22(5)
3.3.3 Organizing your data records
27(2)
3.4 Some tips on report and thesis preparation
29(11)
3.4.1 Sections of a report or thesis
31(1)
3.4.2 Planning a report or thesis
31(2)
3.4.3 Writing the report or thesis
33(7)
Bibliography
40(1)
Chapter 4 Equipping the laboratory and the bench
41(24)
4.1 Introduction
41(1)
4.2 Setting up the laboratory
41(1)
4.3 General laboratory equipment
42(6)
4.3.1 Rotary evaporators
42(1)
4.3.2 Refrigerator and/or freezer
42(1)
4.3.3 Glass-drying ovens
42(1)
4.3.4 Vacuum oven
43(1)
4.3.5 Balances
43(1)
4.3.6 Kugelrohr bulb-to-bulb distillation apparatus
43(1)
4.3.7 Vacuum pumps
43(1)
4.3.8 Inert gases
44(1)
4.3.9 Solvent stills
45(1)
4.3.10 General distillation equipment
46(1)
4.3.11 Large laboratory glassware
47(1)
4.3.12 Reaction monitoring
48(1)
4.4 The individual bench
48(10)
4.4.1 Routine glassware
49(1)
4.4.2 Additional personal items
50(1)
4.4.3 Specialized personal items
50(1)
4.4.3.1 Double manifold
50(3)
4.4.3.2 Three-way Quickfit gas inlet T taps
53(1)
4.4.3.3 Filtration aids
54(2)
4.4.3.4 Glassware for chromatography
56(2)
4.5 Equipment for parallel experiments
58(3)
4.5.1 Simple reactor blocks that attach to magnetic stirrer hot plates
59(1)
4.5.2 Stand-alone reaction tube blocks
60(1)
4.5.3 Automated weighing systems
60(1)
4.5.4 Automated parallel dosing and sampling systems
61(1)
4.6 Equipment for controlled experimentation
61(4)
4.6.1 Jacketed vessels
61(1)
4.6.2 Circulating heater-chillers
62(1)
4.6.3 Peltier heater-chillers
63(1)
4.6.4 Syringe pumps
63(1)
4.6.5 Automated reaction control systems
63(1)
4.6.6 All-in-one controlled reactor and calorimeter systems
63(2)
Chapter 5 Purification and drying of solvents
65(16)
5.1 Introduction
65(1)
5.2 Purification of solvents
65(1)
5.3 Drying agents
66(4)
5.3.1 Alumina, A1203
67(1)
5.3.2 Barium oxide, BaO
67(1)
5.3.3 Boric anhydride, B203
67(1)
5.3.4 Calcium chloride, CaCl2
67(1)
5.3.5 Calcium hydride, CaH2
68(1)
5.3.6 Calcium sulfate, CaS04
68(1)
5.3.7 Lithium aluminum hydride, LiAIH4
68(1)
5.3.8 Magnesium, Mg
68(1)
5.3.9 Magnesium sulfate, MgSO4
68(1)
5.3.10 Molecular sieves
68(1)
5.3.11 Phosphorus pentoxide, P2O5
69(1)
5.3.12 Potassium hydroxide, KOH
69(1)
5.3.13 Sodium, Na
69(1)
5.3.14 Sodium sulfate, Na2SO4
70(1)
5.4 Drying of solvents
70(9)
5.4.1 Solvent drying towers
70(1)
5.4.2 Solvent stills
71(3)
5.4.3 Procedures for purifying and drying common solvents
74(5)
5.4.4 Karl Fisher analysis of water content
79(1)
References
79(2)
Chapter 6 Reagents: Preparation, purification, and handling
81(36)
6.1 Introduction
81(1)
6.2 Classification of reagents for handling
81(1)
6.3 Techniques for obtaining pure and dry reagents
82(5)
6.3.1 Purification and drying of liquids
83(2)
6.3.2 Purifying and drying solid reagents
85(2)
6.4 Techniques for handling and measuring reagents
87(20)
6.4.1 Storing liquid reagents or solvents under an inert atmosphere
87(2)
6.4.2 Bulk transfer of a liquid under inert atmosphere (cannulation)
89(2)
6.4.3 Using cannulation techniques to transfer measured volumes of liquid under inert atmosphere
91(3)
6.4.4 Use of syringes for the transfer of reagents or solvents
94(8)
6.4.5 Handling and weighing solids under inert atmosphere
102(5)
6.5 Preparation and titration of simple organometallic reagents and lithium amide bases
107(6)
6.5.1 General considerations
107(2)
6.5.2 Preparation of Grignard reagents (e.g., phenylmagnesium bromide)
109(1)
6.5.3 Titration of Grignard reagents
109(1)
6.5.4 Preparation of organolithium reagents (e.g., n-butyllithium)
110(1)
6.5.5 Titration of organolithium reagents (e.g., n-butyllithium)
111(1)
6.5.6 Preparation of lithium amide bases (e.g., lithium diisopropylamide)
112(1)
6.6 Preparation of diazomethane
113(2)
6.6.1 Safety measures
113(1)
6.6.2 Preparation of diazomethane (a dilute ethereal solution)
113(2)
6.6.3 General procedure for esterification of carboxylic acids
115(1)
6.6.4 Titration of diazomethane solutions
115(1)
References
115(2)
Chapter 7 Gases
117(14)
7.1 Introduction
117(1)
7.2 Use of gas cylinders
117(3)
7.2.1 Fitting and using a pressure regulator on a gas cylinder
118(2)
7.3 Handling gases
120(2)
7.4 Measurement of gases
122(5)
7.4.1 Measurement of a gas using a standardized solution
122(1)
7.4.2 Measurement of a gas using a gas-tight syringe
123(1)
7.4.3 Measurement of a gas using a gas burette
123(2)
7.4.4 Quantitative analysis of hydride solutions using a gas burette
125(1)
7.4.5 Measurement of a gas by condensation
126(1)
7.4.6 Measurement of a gas using a quantitative reaction
126(1)
7.5 Inert gases
127(1)
7.6 Reagent gases
127(3)
7.6.1 Gas scrubbers
128(1)
7.6.2 Methods for preparing some commonly used gases
128(2)
References
130(1)
Chapter 8 Vacuum pumps
131(6)
8.1 Introduction
131(1)
8.2 House vacuum systems (low vacuum)
131(1)
8.3 Medium vacuum pumps
131(2)
8.3.1 Water aspirators
131(1)
8.3.2 Electric diaphragm pumps
132(1)
8.4 High vacuum pumps
133(2)
8.4.1 Rotary oil pumps
133(1)
8.4.2 Vapor diffusion pumps
134(1)
8.5 Pressure measurement and regulation
135(2)
8.5.1 Units of pressure (vacuum) measurement
136(1)
Chapter 9 Carrying out the reaction
137(54)
9.1 Introduction
137(1)
9.2 Reactions with air-sensitive reagents
138(15)
9.2.1 Introduction
138(1)
9.2.2 Preparing to carry out a reaction under inert conditions
138(1)
9.2.3 Drying and assembling glassware
139(1)
9.2.4 Typical reaction setups using a double manifold
140(1)
9.2.5 Basic procedure for inert atmosphere reactions
140(4)
9.2.6 Modifications to basic procedure
144(5)
9.2.7 Use of balloons for holding an inert atmosphere
149(3)
9.2.8 Use of a "spaghetti" tubing manifold
152(1)
9.3 Reaction monitoring
153(14)
9.3.1 Thin layer chromatography
153(7)
9.3.2 High performance liquid chromatography
160(4)
9.3.3 Gas-liquid chromatography (GC, GLC, VPC)
164(3)
9.3.4 NMR
167(1)
9.4 Reactions at other than room temperature
167(10)
9.4.1 Low-temperature reactions
168(2)
9.4.2 Reactions above room temperature
170(7)
9.5 Driving equilibria
177(1)
9.5.1 Dean-Stark traps
177(1)
9.5.2 High-pressure reactions
178(1)
9.6 Agitation
178(6)
9.6.1 Magnetic stirring
179(1)
9.6.2 Mechanical stirrers
180(2)
9.6.3 Mechanical shakers and vortexers
182(1)
9.6.4 Sonication
183(1)
9.7 Use of controlled reactor systems
184(5)
9.7.1 Jacketed vessels
185(1)
9.7.2 Parallel reactors
186(3)
References
189(2)
Chapter 10 Working up the reaction
191(18)
10.1 Introduction
191(1)
10.2 Quenching the reaction
191(7)
10.2.1 Strongly basic nonaqueous reactions
192(1)
10.2.2 Near neutral nonaqueous reactions
192(1)
10.2.3 Strongly acidic nonaqueous reactions
193(1)
10.2.4 Nonaqueous reactions involving A1 (III) reagents
193(2)
10.2.5 Reactions involving oxidizing mixtures that may contain peroxide residues
195(1)
10.2.6 Acidic or basic aqueous reactions
195(1)
10.2.7 Liquid ammonia reactions
195(2)
10.2.8 Reactions involving homogeneous transition metal catalysts
197(1)
10.3 Isolation of the crude product
198(10)
10.3.1 Typical isolation from an aqueous work-up
199(4)
10.3.2 Isolation from a reaction involving nonvolatile polar aprotic solvents
203(1)
10.3.3 Using an acid/base aqueous work-up to separate neutral organics from amines
203(1)
10.3.4 Using an acid/base aqueous work-up to separate neutral organics from carboxylic acids
204(1)
10.3.5 Nonaqueous work-ups
205(1)
10.3.6 Work-ups using scavenger resins
206(1)
10.3.7 Use of scavengers to remove heavy metal residues
207(1)
10.4 Data that need to be collected on the crude product prior to purification
208(1)
Chapter 11 Purification
209(40)
11.1 Introduction
209(1)
11.2 Crystallization
209(9)
11.2.1 Simple crystallization
209(3)
11.2.2 Small-scale crystallization
212(2)
11.2.3 Crystallization at low temperatures
214(3)
11.2.4 Crystallization of air-sensitive compounds
217(1)
11.3 Distillation
218(10)
11.3.1 Simple distillation
218(2)
11.3.2 Distillation under an inert atmosphere
220(1)
11.3.3 Fractional distillation
221(2)
11.3.4 Distillation under reduced pressure
223(3)
11.3.5 Small-scale distillation
226(2)
11.4 Sublimation
228(1)
11.5 Flash chromatography
229(11)
11.5.1 Equipment required for flash chromatography
230(2)
11.5.2 Procedure for running a flash column
232(7)
11.5.3 Recycling silica for flash chromatography
239(1)
11.6 Dry-column flash chromatography
240(1)
11.7 Preparative TLC
241(1)
11.8 Medium pressure and prepacked chromatography systems
242(3)
11.9 Preparative HPLC
245(3)
11.9.1 Equipment required
245(1)
11.9.2 Running a preparative HPLC separation
246(2)
References
248(1)
Chapter 12 Small-scale reactions
249(10)
12.1 Introduction
249(1)
12.2 Reactions at or below room temperature
250(2)
12.3 Reactions above room temperature
252(1)
12.4 Reactions in NMR tubes
253(2)
12.5 Purification of materials
255(4)
12.5.1 Distillation
255(1)
12.5.2 Crystallization
255(1)
12.5.3 Chromatography
255(4)
Chapter 13 Large-scale reactions
259(8)
13.1 Introduction
259(2)
13.2 Carrying out the reaction
261(2)
13.2.1 Using standard laboratory equipment
261(1)
13.2.2 Using a jacketed vessel
261(2)
13.3 Work-up and product isolation
263(3)
13.4 Purification of the products
266(1)
Chapter 14 Special procedures
267(10)
14.1 Introduction
267(1)
14.2 Catalytic hydrogenation
267(3)
14.3 Photolysis
270(2)
14.4 Ozonolysis
272(1)
14.5 Flash vacuum pyrolysis (FVP)
273(1)
14.6 Liquid ammonia reactions
274(1)
14.7 Microwave reactions
275(1)
References
276(1)
Chapter 15 Characterization
277(8)
15.1 Introduction
277(1)
15.2 NMR spectra
277(3)
15.3 IR spectra
280(1)
15.4 UV spectroscopy
280(1)
15.5 Mass spectrometry
281(1)
15.6 Melting point (m.p.) and boiling point (b.p.)
281(1)
15.7 Optical rotation
281(1)
15.8 Microanalysis
282(1)
15.9 Keeping the data
283(2)
Chapter 16 Troubleshooting: What to do when things don't work
285(4)
Chapter 17 The chemical literature
289(12)
17.1 Structure of the chemical literature
289(1)
17.2 Some important paper-based sources of chemical information
290(4)
17.2.1 Chemical Abstracts
290(1)
17.2.2 Beilstein
291(1)
17.2.3 Science Citation Index (paper copy)
292(2)
17.3 Some important electronic-based sources of chemical information
294(2)
17.3.1 SciFinder
295(1)
17.3.2 Reaxys
295(1)
17.3.3 Web of Science and SCOPUS
295(1)
17.3.4 Cambridge Structural Database (CSD)
296(1)
17.3.5 The World Wide Web
296(1)
17.4 How to find chemical information
296(2)
17.4.1 How to do searches
296(1)
17.4.2 How to find information on specific compounds
297(1)
17.4.3 How to find information on classes of compounds
297(1)
17.4.4 How to find information on synthetic methods
298(1)
17.5 Current awareness
298(1)
References
299(2)
Appendix 1 Properties of common solvents 301(4)
Appendix 2 Properties of common gases 305(4)
Appendix 3 Approximate pKa values for some common reagents versus common bases 309(2)
Appendix 4 Common Bronsted acids 311(2)
Appendix 5 Common Lewis acids 313(2)
Appendix 6 Common reducing reagents 315(4)
Appendix 7 Common oxidizing reagents 319(4)
Index 323
John Leonard is currently a principal scientist at AstraZeneca Pharmaceuticals, where he is primarily involved with synthetic route design and development activities. Prior to this he was a professor of organic chemistry at the University of Salford, UK.Garry Procter is a professor and director of teaching in the School of Chemistry at the University of Manchester, UK. Before this he was director of undergraduate laboratories in the Department of Chemistry and Chemical Biology at Harvard University.Barry Lygo is currently a professor of chemistry at the University of Nottingham, UK, working in the field of asymmetric catalysis and synthesis.