Organic Chemistry Laboratory

CHEM 132 - Winter Quarter 2018 - Instructor: Brennan, M. K.

Library resources for students taking organic chemistry laboratory courses.

Best practices

"Zubrick provides students with a valuable guide to the basic techniques of the Organic Chemistry lab. The book will help students understand and practice good lab safety. It will also help students become familiar with basic instrumentation, techniques and apparatus and help them master the latest techniques such as interpretation of infrared spectroscopy." (publisher's description)
"This book offers prudent practices designed to promote safety and includes practical information on assessing hazards, managing chemicals, disposing of wastes, and more. Prudent It serves as a leading source of chemical safety guidelines for people working with laboratory chemicals: research chemists, technicians, safety officers, educators, and students." -Publisher's description.
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Laboratory Safety for Chemistry Students
Second edition.
Science Library (Li and Ma) » Safety Collection » QD63.5 .H55 2016
"Provides knowledge and models of good practice needed by students to work safely in the laboratory as they progress through four years of undergraduate laboratory work." (publisher's description)
Safety in Academic Chemistry Laboratories, 8th Edition
8th edition.
Science Library (Li and Ma) » Safety Collection » QD63.5 .S24 2017
"This publication provides students with an overview of the key issues related to the safe use of chemicals in the first two years of an undergraduate program in chemistry.  Some changes in the new edition include:
• A new introduction that sets basic laboratory safety information in the context of developing a culture of safety in chemical laboratories.
• A review of common personal protective equipment and various safety practices in laboratories.
• A guide to chemical hazards, how to recognize them, and sources of information about chemical hazards, including the GHS.
• An overview of safety concerns for many common laboratory techniques.
• An overview of safety equipment and emergency response procedures for fires, spills, and chemical exposures.
• The addition of sidebars, for interest and readability, and “In Your Future” sections for common laboratories hazards and concerns that are less likely to be encountered in introductory and organic laboratories but about which all students should be aware.
• A content shift from safety based primarily on rules to learning about safety through the RAMP (Recognize the hazards, Assess the risks of the hazards, Minimize the risks of the hazards and Prepare for emergencies ) principles." (publisher's description) 

Lab safety

More safety information resources

[Silver Spring, Md.] : U.S. National Oceanic and Atmospheric Administration, National Ocean Service, Office of Response and Restoration, 2007-
Stanford Libraries » Online resource » eResource
"Find response information for thousands of hazardous materials, including fire and explosion hazards, health hazards, firefighting techniques, cleanup procedures, protective clothing, and chemical properties.  Use "My Chemicals" to build a list of chemicals. Explore reactivity, see what hazards might occur if chemicals in your MyChemicals collection are mixed together.  CAMEO Chemicals contains: A library with thousands of datasheets containing response-related information and recommendations for hazardous materials that are commonly transported, used, or stored in the United States. A reactivity prediction tool, which you can use to predict potential reactive hazards between chemicals. This tool is part of the CAMEO software suite, and it is available as a website, mobile website, and as a downloadable version that you can run on your own computer." - (Publisher's description).
[New York] : John Wiley & Sons, c2001-
Stanford Libraries » Online resource » eResource
"This on-line work utilizes the full potential of the web by allowing alphanumeric searches through e-EROS and across all Wiley products, and by allowing chemical structure, substructure and reaction searching straight from a chemist's desktop. It contains a database of around 70,000 reactions and around 4000 of the most frequently consulted reagents and is fully searchable by structure and substructure, reagent, reaction type, experimental conditions etc. and allows sophisticated full text searches. e-EROS offers a systematic and exhaustive coverage of reagents used in organic synthesis. The Editorial Board are keeping e-EROS up-to-date by regularly adding new reagents and catalysts, and by updating existing articles whenever felt necessary. The A to Z listing covers classical reagents, new "designer" reagents and catalysts." (Structure Searching)
Stanford Libraries » Online resource » eResource
The Laboratory Chemical Safety Summary (LCSS) is based on the format described by the National Research Council in the publication "Prudent Practices in the Laboratory: Handling and Management of Chemical Hazards" (2011).
6th ed. Burlington : Elsevier Science, 2011.
Stanford Libraries » Online resource » eResource
"Sittig's 5th Edition remains the lone comprehensive work providing a vast array of critical information on the 2,100 most heavily used, transported, and regulated chemical substances of both occupational and environmental concern. It provides extensive data for each chemical substances in a uniform format. The chemicals are presented alphabetically and classified as a carcinogen, hazardous substance, hazardous waste, or toxic pollutant. Chemicals classified as WMD have been included in the new edition as has more information frequently queried by first responders and frontline industrial safety personnel." - Publisher's description.

Properties

[Frankfurt, Germany ; New York, NY] : Elsevier
Stanford Libraries » Online resource » eResource
Available via the web, Reaxys Xcelerate contains an extensive repository of experimentally validated data that chemists need including structures, reactions (including multi-step reactions) and physical properties. Reaxys was formed by the merger of three databases: Beilstein Handbook of Organic Chemistry, Gmelin Handbook of Inorganic and Organometallic Chemistry, and the Chemistry Patent database. (Structure and Reaction Searching)
Milwaukee, WI : Sigma-Aldrich
Science Library (Li and Ma) » Reference » TP247 .A4 2012/2014
Catalog offering more than 40,000 research chemicals. Search by chemical name, molecular formula, CAS Registry Number, and by substructure. Information about a compound usually includes identification information, chemical structure, physical and chemical properties, as well as links to materials safety data sheets and to spectral diagrams.
Cleveland, Ohio, CRC Press.
Green Library » Information Center: Reference » QD65 .H3 ED.100 2019/2020
Continues to be the most accurate, reliable and current resource available on data needed by chemists, physicists and engineers. It provides wide coverage of data on properties of inorganic and organic compounds. Now searchable by chemical structure. Note: Appendix B contains sources of physical and chemical data.
Boca Raton, FL : Chapman & Hall/CRC Press
Stanford Libraries » Online resource » eResource
Includes descriptive and numerical data on the chemical, physical and biological properties of compounds; systematic and common names of compounds; literature references; structure diagrams and their associated connection tables. CCD online includes: organic compounds (269,000 records); natural products (178,000 records); inorganic and organometallic compounds (103,000 records); drugs (44,000 records); analytical reagents (14,000 records); and carbohydrates (24,000). (Structure searching)
Rahway, N.J. : Merck & Co., 1968-
Green Library » Information Center: Reference » RS356 .M524 2001
The Merck Index contains over 10,000 monographs with information relating to compounds of significance in research, commerce and environmental impact.  Each monograph in this authoritative reference source is a concise description of a single substance or a small group of closely related compounds. There is also a supplement of Organic Name Reactions.
Boca Raton, FL : Chapman & Hall/CRC Press
Stanford Libraries » Online resource » eResource
Part of the CHEMnetBASE collection, the Properties of Organic Compounds is a database that contains over 29,000 of the most commonly sought organic compounds, featuring physical data, spectral data, and structures. With a high quality display and powerful search capabilities, it acts as an easy-to-use tool for identifying unknown compounds or for locating additional data and references for a known compound. Search by spectral peak, molecular formula/elements, properties, and substructure. (Structure searching)

Spectra

This page contains spectral databases, print handbooks, and textbooks.  It is possible to search by spectral peaks in SDBS and Properties of Organic Compounds.   In SciFinder, explore by Substance > Substance Identifier (e.g. chemical name).  View detailed substance information to see experimental and predicted spectral diagrams.

Japan : AIST
Stanford Libraries » Online resource » eResource
SDBS includes 6 different types of spectra under a directory of the compounds. The six spectra are as follows, an electron impact Mass spectrum (EI-MS), a Fourier transform infrared spectrum (FT-IR), a 1H nuclear magnetic resonance (NMR) spectrum, a 13C NMR spectrum, a laser Raman spectrum, and an electron spin resonance (ESR) spectrum. It is possible to search by compound name, molecular formula, molecular weight, CAS Registry Number, number of atoms, and spectral peaks.
Boca Raton, FL : Chapman & Hall/CRC Press
Stanford Libraries » Online resource » eResource
Part of the CHEMnetBASE collection, the Properties of Organic Compounds is a database that contains over 29,000 of the most commonly sought organic compounds, featuring physical data, spectral data, and structures. With a high quality display and powerful search capabilities, it acts as an easy-to-use tool for identifying unknown compounds or for locating additional data and references for a known compound. Search by spectral peak, molecular formula/elements, properties, and substructure. (Structure searching)
[Columbus, Ohio : American Chemical Society, Chemical Abstracts Service]
Stanford Libraries » Online resource » eResource
SciFinder is the most comprehensive database for coverage of chemistry & chemical engineering. It has the world's largest collection of organic and inorganic substance information. The web version of SciFinder provides integrated access to CAPlus, CAS Registry, CASREACT, CHEMLIST, and CHEMCATS which are produced by Chemical Abstracts Service, and to MEDLINE which is produced by the U.S. National Library of Medicine. Sources covered in SciFinder include 10,000 journals, patents from 63 patent authorities, book chapters, conference proceedings, dissertations, evaluated reference works, technical reports, as well as book reviews and biographical information. Also includes access to MethodsNow, a curated collection of methods in analytical and synthetic chemistry. (Structure and Reaction Searching)

Spectra handbooks

Ed. 3. Milwaukee, Wis. (940 W. St. Paul Ave., Milwaukee 53233) : Aldrich Chemical Co., c1981.
Science Library (Li and Ma) » Reference » QD96 .I5 P67 1981
Includes more than 12,000 spectra classified by functional group and structural presentation.
Ed. 1. Milwaukee, Wis. : Aldrich Chemical Co., c1985-1989.
SAL3 (off-campus storage) » Stacks » QD96 .I5 P66 1985 F V.1
This three volume set includes over 18,000 spectra categorized by chemical functionality and arranged in order of increasing structural complexity.
Ed. 1 Milwaukee : Aldrich Chemical Co., c1993.
Science Library (Li and Ma) » Reference » QC462.85 .A44 1993 F V.1
This three volume set of 12,000 high-resolution 75MHz 13C and 300MHz 1H FT-NMR spectra is arranged according to functionality.
Ed. 2. Milwaukee, Wis. (P.O. Box 355, Milwaukee 53201) : Aldrich Chemical Co., c1983.
Science Library (Li and Ma) » Reference » QD96 .N8 P68 1983 F V.1
A two volume set of more than 8,500 60MHz 1H NMR spectra.
3rd ed. Chichester ; New York : Wiley, 2001.
Science Library (Li and Ma) » Reference » QC457 .S69 2001
This revised text but has been extended to meet the interpretive needs of Raman users as well as those working in the IR region. The result is a uniquely practical, comprehensive and detailed source for spectral interpretation. Combining in one volume, the correlation charts and tables for spectral interpretation for these two complementary techniques, this book will be of great benefit to those using or considering either technique.

Spectra Textbooks

"First published over 40 years ago, this was the first text on the identification of organic compounds using spectroscopy. This text presents a unified approach to the structure determination of organic compounds based largely on mass spectrometry, infrared (IR) spectroscopy, as well as multinuclear and multidimensional nuclear magnetic resonance (NMR) spectroscopy. The key strength of this text is the extensive set of practice and real-data problems (in Chapters 7 and 8). Even professional chemists use these spectra as reference data. Spectrometric Identification of Organic Compounds is written by and for organic chemists, and emphasizes the synergistic effect resulting from the interplay of spectra. This text is characterized by its problem-solving approach with numerous practice problems and extensive reference charts and tables." (publisher's description)
4., rev. and enl. ed. / Berlin ; Heidelberg : Springer. c2009.
Stanford Libraries » Online resource » eResource
This fourth edition of the highly successful and concise textbook contains about 20 % new data. Now included are chapters on 19F and 31P NMR as well as references to important Raman bands. With their unique approach of presenting - in the form of texts, tables, charts, and graphs - a succinct compilation of essential reference data for the interpretation of NMR, IR, UV/Vis, and mass spectra, the authors also provide a hands-on guide for interpreting experimental spectral data and elucidating the structure of the respective compounds behind them.
8th ed. Hoboken, NJ : J. Wiley, c2004.
Science Library (Li and Ma) » Stacks » QD261 .S965 2004
Dedicated to qualitative organic chemistry, this book explains how to identify organic compounds through step-by-step instructions. Topics include elemental analysis, solubility, infrared, nuclear magnetic resonance and mass spectra; classification tests; and preparation of a derivative. Most directions for experiments are described in micro or mini scales. Discusses chromatography, distillations and the separation of mixtures. Questions and problems emphasize the skills required in identifying unknown samples.

Reactions & articles

Dictionary of Organic Compounds

The Dictionary of Organic Compounds includes key literature references to spectra, crystallography, synthesis, and review papers.

Locating full-text from references:

  • Enter reference into Citation Linker on the eJournals page to see if the full-text is available online
  • Search journal title in SearchWorks, Stanford Libraries Catalog, to see if the library has the print or online version
Boca Raton, FL : Chapman & Hall/CRC Press
Stanford Libraries » Online resource » eResource
The Dictionary of Organic Compounds (DOC), part of CHEMnetBASE, contains chemical, structural, and bibliographic information on over 290,000 of the most important organic compounds. Data provided includes names and synonyms, formulae, chemical structures, CAS Registry numbers, physical properties, and key literature citations. Search by properties, molecular formula, and substructure.Data provided includes names and synonyms, formulae, chemical structures, CAS Registry numbers, physical properties, and key literature citations. Search by properties, molecular formula, and substructure. (Str)

Largest chemistry databases

It is possible to search Reaxys and SciFinder by a chemical structure, reaction scheme, and bibliographic data.  Reaxys is the largest handbook of physical property data and includes links to articles that contain spectra.  SciFinder is the largest chemistry database and is compiling handbook type of information - properties and links to spectral diagrams - in the full display of chemical substance records.

[Columbus, Ohio : American Chemical Society, Chemical Abstracts Service]
Stanford Libraries » Online resource » eResource
SciFinder is the most comprehensive database for coverage of chemistry & chemical engineering. It has the world's largest collection of organic and inorganic substance information. The web version of SciFinder provides integrated access to CAPlus, CAS Registry, CASREACT, CHEMLIST, and CHEMCATS which are produced by Chemical Abstracts Service, and to MEDLINE which is produced by the U.S. National Library of Medicine. Sources covered in SciFinder include 10,000 journals, patents from 61 patent authorities, book chapters, conference proceedings, dissertations, evaluated reference works, technical reports, as well as book reviews and biographical information. (Str, Rxn)
[Frankfurt, Germany ; New York, NY] : Elsevier
Stanford Libraries » Online resource » eResource
Reaxys Xcelerate is a fully integrated electronic chemistry database that contains organic, inorganic and organometallic substance, property, and reaction data for small molecules housed previously in the Beilstein, Gmelin, and Chemistry Patent databases. Includes coverage from 1771-present for 400 journals. Coverage also includes English language-only patents from the major chemistry patent classes of the U.S., European, and World Patent Offices. Reaxys Xcelerate is a premium version of Reaxys that allows faster analysis of results using visualization tools, automate synthesis planning, and use flexible reporting outputs for sharing their results and annotations with colleagues. (Str, Rxn)

Major interdisciplinary databases

Stanford Libraries » Online resource » eResource
Search over 12,000 core journals across the sciences, social sciences, and arts and humanities to find the high quality research. Move backward/forward in time using cited/citing reference identified by researchers. Updated weekly, includes Science Citation Index Expanded (1899-present), Social Sciences Citation Index (1898-present), Arts & Humanities Citation Index (1975-present), Conference Proceedings Citation Index- Science (1990-present), Conference Proceedings Citation Index- Social Science & Humanities (1990-present), Book Citation Index (2005-present), Index Chemicus (1993-present), and Current Chemical Reactions (1985-present; also includes Institut National de la Propriete Industrielle structure data back to 1840)). (Structure searching)
Santa Fe, N.M.: Deep Web Technologies
Stanford Libraries » Online resource » eResource
xSearch enables Stanford students and researchers to search multiple resources at one time.  The 350+ resources in xSearch include abstracts and indexes, datasets, full-text ejournal and ebooks, funding opportunities, methods and protocols, patents, streaming media, technical reports, plus more.  A Chemical Safety Search site that includes 70+ resources is also available.

Additional resources

Hoboken, N.J. : John Wiley, c2009.
Stanford Libraries » Online resource » eResource
With its coverage of 701 organic name reactions and reagents, this online reference is the largest, most up-to-date work of its kind. It offers students and professional chemists a valuable resource for conducting experiments and performing a broad range of applications, from pharmaceuticals to plastics to pesticides. Each reaction listing is clearly organized into uniform sections that allow readers to quickly gather the information they need to conduct their own experimental procedures.
[New York] : John Wiley & Sons, c2001-
Stanford Libraries » Online resource » eResource
e-EROS combines the complete text of the encyclopedia with the sophistication of a database including all the chemical reactions and structures. It contains a database of around 50,000 reactions and around 3250 of the most frequently consulted reagents and is fully searchable by structure and substructure, reagent, reaction type, experimental conditions, etc. and allows sophisticated full text searches. Offers systematic and exhaustive coverage of reagents used in organic synthesis. Kept up-to-date by regularly adding new reagents and catalysts, and by updating existing articles. The A to Z listing covers classical reagents, new "designer" reagents and catalysts. (Str)
Organic Reactions (new image)
New York : John Wiley & Sons, 1942-
Marine Biology Library (Miller) » Stacks » QD251 .O7 V.16
Currently containing over 140,000 reactions, Organic Reactions is a comprehensive collection of important synthetic reactions, together with a critical discussion of the reaction and tables that organize all published examples of the topic reactions. Chapters that focus on reactions of current interest are solicited by the board of editors from leading chemists worldwide. The publication process entails a comprehensive peer-review process, ensuring the high quality and attention to detail for which this series is noted. Comprehensive coverage of all examples of a given reaction is provided in tabular form. In addition to providing reaction scope, stereochemical aspects, and side reactions, a selection of representative experimental conditions are given. Online access covers Vol. 25, 1977-present. (Str)
New York : John Wiley & Sons, Inc., 1921-
Marine Biology Library (Miller) » Stacks » QD262 .O7 V.52
Collective Vols in Swain Reference QD262 Organic Syntheses describes checked and edited experimental procedures, spanning a broad range of synthetic methodologies, and provides chemists with a compendium of new or little known experimental procedures which lead to useful compounds or that illustrate important new developments in methodology. For every procedure, safety warnings are presented along with detailed descriptions for the preparation, purification, and identification of the compound in question. Additionally, special reaction conditions are detailed, along with the source of reagents, helpful waste disposal guidelines, discussions of results, references to the primary literature, and an appendix of nomenclature and registry numbers. The print version was published in Annual volumes and Collective Volumes. Online access covers, Vol. 1, 1921-present. (Str)
7th ed. Weinheim, Germany : Wiley-VCH ; New York : J. Wiley & Sons, 2009-
Stanford Libraries » Online resource » eResource
This state-of-the-art reference work details the science and technology in all areas of industrial chemistry. Subject areas include: inorganic and organic chemicals, advanced materials, pharmaceuticals, polymers and plastics, metals and alloys, biotechnology and biotechnological products, food chemistry, process engineering and unit operations, analytical methods, environmental protection, etc.

Software

Site-licensed by Science Library

The Robin Li and Melissa Ma Science Library has purchased campus-wide site licenses for several products. Access to all of these products is limited to current Stanford students, faculty, and staff.

Learn more about software at Stanford.

Writing

3rd ed. / Washington, DC : American Chemical Society ; Oxford ; New York : Oxford University Press, 2006.
Earth Sciences Library (Branner) » Stacks » QD8.5 .A25 2006
"An essential constant in this changing environment is the requirement that information remain accurate, clear, unambiguous, and ethically sound. The ACS Style Guide is the definitive source for all information needed to write, review, submit, and edit scholarly and scientific manuscripts. It is also an excellent resource for learning how to effectively communicate scientific information." (publisher's description)
"This compact and easy-to-read book contains essential advice on how to take a manuscript from planning right through to publication. It will help both first-time writers and more experienced authors to present their results more effectively. While retaining the easy-to-read and well-structured approach of previous editions, the third edition of this essential guide has been expanded to include comprehensive advice on drawing graphs, and information about Open Access publishing. Illustrations are discussed in detail, with examples of poor illustrations taken from real papers in top-ranked journals, redrawn for comparison. Such before-and-after examples are also provided to demonstrate good and bad writing styles. The reader is offered practical advice - from how to present a paper and where to submit the manuscript, through to responding to reviewers' comments and correcting the proofs - all developed through the author's extensive teaching experience and his many years spent working as a journal editor." (publisher's description)
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