This information is primarily for students in Chemistry 160 and other classes in which you are requested to find an article that gives a method for synthesis.
Note that the MELVYL System or Scotty (the UCR Library Catalog) is not the best place to start your search. Chemical handbooks and dictionaries are a better first stop.
- Follow up references to the literature given in your lab manual, if there are any. Use the MELVYL System or Scotty to determine whether or not the library owns a particular book or journal. If you don't know how to use the online catalogs, please ask at the reference desk or consult the various handouts available.
- Look in the Merck Index (Ready Ref RS356). Check under the name of your compound. Use the index to determine if there is an alternate name for the compound. Often the short entry will give some literature references. Not all compounds are listed in Merck. If you don't find yours, go on to the next step.
- Try the Aldrich Catalog Handbook of Fine Chemicals (Ready Ref TP202 A54). Even if you don't find a helpful citation to the literature, you will find the Chemical Abstracts Service Registry Number (CAS number). This unique number, for example [98-58-2], will help you to properly identify the compound as you look in other reference books. Look under the name of your compound or a reagent you could use for synthesis.
- Use the Dictionary of Organic Compounds (Ref QD246 D5 1996). Use the formula index, the chemical name index, or the CAS registry number index to identify the correct entry for the compound. Then use the entry number given to refer to the appropriate volume in the main series or supplements. Each compound or series of compounds has references listed at the end. Look for the abbreviation "synth" to find articles that refer to synthesis. To find out whether or not the Library has them, you will need to look them up in Scotty or the MELVYL Catalog. Here are a few common sources and call numbers:
J.A.C.S. = The Journal of the American Chemical Society (Q1 A5)
These two multi-volume sets are shelved in the Physical Sciences Library Reference Collection:
A) Organic Syntheses (Ref QD262 O72). This is often abbreviated as Org. Synth.
B) Reagents for Organic Synthesis, (Ref QD262 F5) often referred to as Feiser & Feiser (the editors).
If you haven't found a reference to your compound already, then you need to use the indexes in one of these two reference sets.
A) Organic Syntheses:
- Check in the Cumulative Index under the name of your compound or under the registry number.
- Alternatively, in the Cumulative Index check the type of reaction, for example: REDUCTION. Then go to the appropriate reaction, for example: C=0 --> CHOH. Check the appropriate volume and page of the main set. I, 90 means Collective Volume 1, page 90.
- You can also look in the Reaction Guide volume. Check the Reductions section for an appropriate subtopic, such as Hydride Reagents. When you find something of interest, you can find more information in one of the Collective Volumes. Decipher the cryptic code OS, CV5, 175 (1973) as Organic Syntheses Collective Volume 5, page 175, 1973.
B) Reagents for Organic Synthesis:
- You can take a general approach by looking in the Type of Reaction Index section under the type of reaction, such as REDUCTION REACTIONS. Go to the topic ALDEHYDE KETONE --> ROH. You have many reagents to pick from, but be aware that not all of them will be available in the Stockroom, so use your judgement. You will find volume and page references into the main volumes of the set. For example, you can decode the cite 11, 216 as volume 11, page 216.
- Alternatively, in the Collective Index volume look under the reagent of interest. In the section labeled Reagents Index you can check under a specific name, such as sodium borohydride.
WORDS OF ADVICE
- For chemistry-related questions, please ask one of the TAs. For questions on how to use library materials, please ask one of the librarians.
- You might wish to check the references contained in the procedures given, because they might lead you to alternative procedures.
- You should be able to find your compounds fairly easily, since they are for a lab and not intended to be too hard to find. If you are having trouble, check your chemical name. Often chemicals can be referred to by different names. Ask your TA or a reference librarian for help in using the reference books or in how to interpret the references.
- Chemistry 166 (certain years only!) In Appendix 5 of the lab manual you may find a list of reagents, typical solvents, and functional groups reduced. This will help in figuring out a procedure and what topics to look up in either Reagents for Organic Synthesis or Organic Syntheses.
- You may come across references to Beil. That refers to the Beilstein handbook of organic chemistry (Beilstein's Handbuch der organischen chemie) a large multi-volume set (Ref QD 251 B4). Most of it is in German. If you need help using this set, please ask at the Reference Desk or consult the handout: "Searching Beilstein's Handbook."