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Organic Chemistry Laboratory

CHEM 130 / CHEM 132 - Winter Quarter 2015 - Instructor: Vollmer-Snarr, H. / Cox, C.
Last Updated: 4-Aug-2015

Library resources for undergrads taking organic chemistry laboratory courses.

Subject Librarians

Grace Baysinger
Grace Baysinger
Head Librarian and Bibliographer of the Swain Chemistry and Chemical Engineering Library
Chemistry & Chemical Engineering Library (Swain)
(650) 725-1039
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Subjects

Chemistry

Related guides

Lab safety
Chemistry resources for students

Around Stanford

Course Reserves List for CHEM 130
Course Reserves List for CHEM 132

Lab safety

Stanford Links

Stanford University Laboratory Chemical Safety Toolkit

A online compendium on how to work safely with chemicals in laboratories at Stanford. Includes these reference information sources: Chemical Hazard Classes, Laboratory Chemical Safety Sheets, Material Safety Data Sheets, Stanford Lab Safety Data Sheets, and TOXNET.

Stanford E-MSDS (Electronic Material Safety Data Sheets)

Stanford EH&S has licensed MSDS from Chemwatch, an electronic MSDS provider. Chemwatch provides access to over 1 million MSDS documents.

Safety Resources

Canadian Centre for Occupational Health and Safety. Web information service [electronic resource].
[Hamilton, Ont. : Canadian Centre for Occupational Health and Safety, 1999?-
Stanford University Libraries » Online resource » (no call number)
CCOHS Web Information Service presents a collection of databases related to occupational health and safety: Material Safety Data Sheets, CHEMINFO (safety info for important workplace chemicals), CHEMpendium (metasearch for chemical hazard information from many sources), Registry of Toxic Effects of Chemical Substances, OSH References (index to literature), Canadian enviroOSH (indexes Canadian environmental and occupational safety legislation and standards).
Laboratory safety for chemistry students / Robert H. Hill, Jr., David C. Finster.
Hoboken, N.J. : Wiley, c2010.
Chemistry & ChemEng Library (Swain) » Safety Collection (non-circulating) » QD51 .H55 2010
This book is uniquely designed to accompany students throughout their four-year undergraduate education and beyond, progressively teaching them the skills and knowledge they need to learn their science and stay safe while working in any lab.
The organic chem lab survival manual : a student's guide to techniques / James W. Zubrick.
8th ed. Hoboken, NJ : John Wiley, c2011.
Chemistry & ChemEng Library (Swain) » Stacks » QD261 .Z83 2011
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.
Prudent practices in the laboratory [electronic resource] : handling and management of chemical hazards / Committee on Prudent Practices in the Laboratory, Board on Chemical Sciences and Technology, Division on Earth and Life Studies, National Research Council of the National Academies.
Updated version. Washington, D.C. : National Academies Press, c2011.
Stanford University Libraries » Online resource » (no call number)
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.
Safety in Academic Chemistry Laboratories
Safety in academic chemistry laboratories [electronic resource].
7th ed. Washington, D.C. : American Chemical Society, Joint Board-Council Committee on Chemical Safety, c2003.
Stanford University Libraries » Online resource » (no call number)
One of the most widely used laboratory safety guidance documents available today. Contents: v. 1. Accident prevention for college and university students. v. 2. Accident prevention for faculty and administrators.

The Safety Song

A musical extravaganza on the importance and execution of laboratory safety.

Properties quick search

Finding Properties/Spectra for Known Substance

  • (Str) = can search by chemical structure. 
Aldrich chemistry : handbook of fine chemicals.
Milwaukee, WI : Sigma-Aldrich
Chemistry & ChemEng Library (Swain) » Reference (non-circulating) » 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. (Str)
This database allows users to search the NLM ChemIDplus database of over 370,000 chemicals. A user may enter compound identifiers such as Chemical Name, CAS Registry Number, Molecular Formula, Classification Code, Locator Code, and Structure or Substructure. New searchable features include search and display by Toxicity indicators such as Median Lethal Dose (LD50), by Physical/Chemical Properties such as LogP, and by Molecular Weight. (Str)
CRC Handbook of Chemistry and Physics
CRC handbook of chemistry and physics.
Cleveland, Ohio, CRC Press.
Green Library » InfoCenter: Ready Reference (non-circulating) » QD65 .H3 95TH 2014/2015
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. Some of the most heavily used tables were recently updated and expanded including: Physical Properties of Inorganic Compounds; Enthalpy of Fusion; Bond Dissociation Energies; Table of the Isotopes; Inorganic Ion and Ligand Nomenclature; Chemical Carcinogens; and Global Temperature Trends for the past 150 years.
Hazardous substances data bank [electronic resource] : HSDB.
Bethesda, Md. : National Library of Medicine, [199-]-
Stanford University Libraries » Online resource » (no call number)
Comprehensive, peer-reviewed toxicology data for about 5,000 chemicals. Broad scope in human and animal toxicity, safety and handling, environmental fate, and more.
The Merck index.
Rahway, N.J. : Merck & Co., 1968-
Green Library » InfoCenter: Ready Reference (non-circulating) » RS356 .M524 2001
Contains 10,955 monographs describing significant chemicals, drugs, and biological substances. The information provided includes chemical, common and generic names, trademarks and their associated companies, Chemical Abstracts Service (CAS) Registry Numbers, molecular formulas and weights, physical and toxicity data, therapeutic and commercial uses, citations to the chemical, biomedical and patent literature, and chemical structures. (Str)
Spectral database for organic compounds SDBS [electronic resource].
Japan : AIST
Stanford University Libraries » Online resource » (no call number)
SDBS has a new URL: SDBS is an integrated spectral database system for organic compounds,which includes 6 different types of spectra under a directory of the compounds. The six spectra are: 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. (Str)

Print spectral resources

Swain Reference Books on Spectra

The Aldrich library of infrared spectra / Charles J. Pouchert.
Ed. 3. Milwaukee, Wis. (940 W. St. Paul Ave., Milwaukee 53233) : Aldrich Chemical Co., c1981.
Chemistry & ChemEng Library (Swain) » Reference (non-circulating) » QD96.I5 P67 1981
Includes more than 12,000 spectra classified by functional group and structural presentation.
The Aldrich library of FT-IR spectra / Charles J. Pouchert.
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.
The Aldrich library of ¹³C and ¹H FT NMR spectra / [edited by] Charles J. Pouchert, Jacqlynn Behnke.
Ed. 1 Milwaukee : Aldrich Chemical Co., c1993.
Chemistry & ChemEng Library (Swain) » Reference (non-circulating) » 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.
The Aldrich library of NMR spectra / Charles J. Pouchert.
Ed. 2. Milwaukee, Wis. (P.O. Box 355, Milwaukee 53201) : Aldrich Chemical Co., c1983.
Chemistry & ChemEng Library (Swain) » Reference (non-circulating) » QD96.N8 P68 1983 F V.1
A two volume set of more than 8,500 60MHz 1H NMR spectra.
Infrared and Raman characteristic group frequencies : tables and charts / George Socrates.
3rd ed. Chichester ; New York : Wiley, 2001.
Chemistry & ChemEng Library (Swain) » Reference (non-circulating) » 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.

Spectral Resources - Selected Textbooks

Spectrometric identification of organic compounds.
7th ed. / Hoboken, NJ : John Wiley & Sons, c2005.
Chemistry & ChemEng Library (Swain) » Stacks » QD272 .S6 S55 2005
First published over 40 years ago, this was the first text on the identification of organic compounds using spectroscopy. This text is now considered to be a classic. The key strength of this text is the extensive set of 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 the spectra. This book is characterized by its problem-solving approach with extensive reference charts and tables.
Structure determination of organic compounds [electronic resource] : tables of spectral data.
4., rev. and enl. ed. / Berlin ; Heidelberg : Springer. c2009.
Stanford University Libraries » Online resource » (no call number)
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.
The systematic identification of organic compounds / Ralph L. Shriner ... [et al.].
8th ed. Hoboken, NJ : J. Wiley, c2004.
Chemistry & ChemEng Library (Swain) » Request at circulation desk » 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.

Compounds, reactions, syntheses

Quick search

  • (Str) = can search by chemical structure
  • (Rxn) = can search by drawing chemical reaction
Properties of organic compounds [electronic resource].
Web version 6.0. Boca Raton, FL : Chapman & Hall/CRC Press, c2002.
Stanford University Libraries » Online resource » (no call number)
POC is a database that contains over 30,000 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. Please download structure drawing plugin the first time you search POC. (Str)
Spectral database for organic compounds SDBS [electronic resource].
Japan : AIST
Stanford University Libraries » Online resource » (no call number)
SDBS has a new URL: 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.

Find Key Literature References

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
CHEMnetBASE [electronic resource] : chemical databases online.
Boca Raton, FL : Chapman & Hall/CRC Press
Stanford University Libraries » Online resource » (no call number)

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)

Search the Two 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.

Reaxys [electronic resource].
[Frankfurt, Germany ; New York, NY] : Elsevier
Stanford University Libraries » Online resource » (no call number)

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)

SciFinder [electronic resource].
[Columbus, Ohio : American Chemical Society, Chemical Abstracts Service]
Stanford University Libraries » Online resource » (no call number)

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)

Check Synthesis, Reaction, & Reference Materials

Beilstein dictionary, German-English : for the users of the Beilstein handbook of organic chemistry.
Frankfurt/ Main : Beilstein Institute, 1988.
SAL3 (off-campus storage) » Stacks » QD251 .B4 B44 1988
Comprehensive organic name reactions and reagents [electronic resource] / Zerong Wang.
Hoboken, N.J. : John Wiley, c2009.
Stanford University Libraries » Online resource » (no call number)
e-EROS [electronic resource] : Encyclopedia of reagents for organic synthesis / Wiley InterScience.
[New York] : John Wiley & Sons, c2001-
Stanford University Libraries » Online resource » (no call number)
Organic Reactions (new image)
Organic reactions.
New York : John Wiley & Sons, 1942-
Chemistry & ChemEng Library (Swain) » Reference (non-circulating) » QD251 .O7 V.86 2015
Organic syntheses : an annual publication of satisfactory methods for the preparation of organic chemicals ...
New York : John Wiley & Sons, Inc., 1921-
Chemistry & ChemEng Library (Swain) » Reference (non-circulating) » QD262 .O723 V.90 2013
Ullmann's encyclopedia of industrial chemistry [electronic resource].
7th ed. Weinheim, Germany : Wiley-VCH ; New York : J. Wiley & Sons, 2009-
Stanford University Libraries » Online resource » (no call number)

Software

Site-licensed by Swain Library

Swain 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.

Some software licensed by Swain Library is also accessible using a web browser and Citrix plugin via CDSERVER. For more information, please see instructions for off-campus access to resources.

ChemOffice Professional / ChemDraw Professional

ChemOffice Professional (win) and ChemDraw Professional (mac) are installed on cluster computers that are located in dorms, libraries and computing clusters. 
 
Read the information below if you want to install the software on your computer.
ChemOffice Professional.
Cambridge, MA : CambridgeSoft
Stanford University Libraries » Online resource » (no call number)
Stanford has campus-wide site license to ChemOffice Professional for Windows and ChemDraw Professional for Macs. Some documentation and training materials from an earlier version of the software is available. Please note: Access to training materials are limited to current students, faculty, and staff at Stanford.

Instructions to Download & Install ChemDraw Professional

1. Account Verification: go to http://sitelicense.cambridgesoft.com/sitelicense.cfm?sid=188 and enter Stanford domain email address. 

2.  Create Account/login to CambridgeSoft website and then view "Services" on middle right side of page.

    a. Download software: click on "My Site License"

    b. Get Registration Code: click on "My Downloads."  (Please contact Grace Baysinger (graceb@stanford.edu) if you do not see a Registration Code.)

3.  Copy and paste Registration Code and activate software during installation process.

Lab reports

The ACS style guide : effective communication of scientific information.
3rd ed. / Washington, DC : American Chemical Society ; Oxford ; New York : Oxford University Press, 2006.
Chemistry & ChemEng Library (Swain) » Request at circulation desk » 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)