Course Description

1. Safety Exam: 20 points
   
2. Quizzes @ 10 points each: 40 points
   
3. Standard experiments @ 100 points each: 600 points
   
   
   Scientific Writing (50 points):
   1. Direct usage/ strong verbs,
   2. Correct grammar/spelling/hypenation,
   3. Correct format,
   4. Clarity and conciseness,
   5. Correct use of abbreviations/lack of slang
      
      
      I will suggest correction to improve the composition of your report. After you have made all appropriate corrections and I have approved the scientific writing in the report, you will submit it to a TA for the grading of experimental content.
      
      
      Experimental Content (50 points):
   6. Yield and purity of product,
   7. Quality of data,
   8. Analysis of data,
   9. Sufficient detail in the write-up,
   10. Significant figures/computations,
   
   
4. Special project: 150 points
   (report: 100, progress and creativity: 50)
   
   
5. Lab Notebook: 50 points
   
   
6. Laboratory Performance (10 points/laboratory period): 140 points
   
   Total = 1000 points

Glassware-in-common: There is a limited supply of glassware for use by everyone in the lab, so it is imperative that the turnover rate be as high as possible and that no "hoarding" occur. Clean glassware immediately after use. A Kimwipe wet with hexane will remove grease. Soap, water, and a brush will clean most glassware. Clean frits by rinsing with an appropriate solvent, and, if this does not suffice, by treating with conc. nitric acid or aqua regia (in the hood), rinsing with water, and drying briefly in the oven. Don't store products in flasks. Transfer products to bottles or vials, or in the case of air-sensitive materials, into ampules.

Base baths: If you put something into the base bath, you must sign the log book, and it is your responsibility to bring the glassware out again by the end of the lab period. Often, it is sufficient to soak a piece of glassware for only a few minutes. Glassware coming out of the bath should be rinsed with water, rinsed with 2 M HCl, rinsed again with water, and dried in the oven. Don't put fritted glassware in the KOH bath, because the KOH will dissolve it.

Hoods: Use the hoods whenever your reaction could produce noxious vapors. You should not have open containers of solvent on the benchtop. Benzene, CS2, and other dangerous solvents should be transferred in the hood. Reactions of iron pentacarbonyl, bromine, liquid phosphines and phosphites, or thiols must be done in a hood, and glassware used in such preparations should be soaked for about 30 min in a solution of Clorox.

Elemental Analysis: Pure samples of liquid and solid products can be analyzed for a variety of elements, including metals, at the microanalytic lab. Only good samples should be submitted, i.e., no crude reaction products. Enough to cover the bottom of a one dram vial is usually sufficient unless several analyses are to be done (note that CHN are usually done on the same portion of sample). The TA must approve your samples for analysis (signature on analysis slip). Indicate on the analysis slip the empirical formula of the compound, the percentages of each element to be analyzed for (to two decimal places in the percentage) and the analyses desired. Samples for analysis should be clean and dry, i.e., free of solvents; dry in vacuum, if possible. Indicate clearly on the analysis slip if the sample is hygroscopic or air sensitive, so that the analyst can take appropriate precautions.

NMR Tubes and NMR Spectra: The TA has a supply of NMR tubes. For a ¹H NMR, add approximately 0.015 g of sample and 0.75 mL of a deuterated solvent to the NMR tube, cap it, label it, and hand it to the TA with a written explanation of the sample type and information needed.

IR Plates and Cells: Mulls for IR spectra are made by grinding some of your compound with a half-drop of Nujol (mineral oil) using a mortar and pestle. The paste that results may be transferred to the IR plates using the pestle. The IR plates are hygroscopic. Keep them in the desiccator until ready for use, and clean them immediately after use with absolute ethanol and a Kimwipe. The IR cells for solution work are very expensive and should be treated carefully. They should be filled only with a glass-and-stainless steel syringe (do not use plastic and rubber syringes). Rinse these immediately after use with several (i.e., three or more) syringe volumes of clean, dry solvent, and dried by gently passing a stream of N₂ (not air!) through them. The gas cell for the vacuum line should be stored in a desiccator when not in use. Always pump away the gas after the IR is obtained.

Ultraviolet Light Sources: CAUTION - protect your eyes! The water jacket for the mercury vapor source is made of quartz, as is the reaction vessel. These are expensive to repair or replace, so handle very gently. Do not handle these pieces where the light passes. Fingerprints "burn" into quartz and cause fogging. Maintain an adequate flow of water through the water jacket, as the lamp is very expensive, too. If you use the Tungsten-Halogen lamp, it should be cooled with a stream of air (passed through a tube of glasswool to remove oil).

Heating and Oil Baths: Heat reaction mixtures with hotplates or heating mantles. Open flames can't be used in the laboratory. Oil baths are better sources of heat than heating mantles, as they provide uniform heat without hot spots. Mineral oil baths and paraffin baths are good to about 150 ¡C, at which they begin to smoke and can catch on fire. Use a silicone oil bath between 150 and 250 ¡C. Do not mix silicone oil with mineral oil. Silicone oil should be put in a labeled bottle after use to avoid confusion.

Vacuum Pumps and Traps: Vacuum pumps must always be trapped with liquid nitrogen. If left on overnight, be sure the dewar is filled and covered with aluminum foil. Always, when turning off the vacuum pump, vent air into it to avoid sucking oil back. Remove the liquid nitrogen trap whenever the trap is open to air to avoid condensing liquid oxygen. Always allow the trap to vent off pressure easily when the trap is taken out of liquid nitrogen, to avoid blowing the trap apart.

Mercury Spills: Report all mercury spills. All mercury spilled must be collected as thoroughly as possible. The contaminated area should be sprinkled with sulfur after collecting as much of the mercury as possible. Waste mercury should be put in the bottles labeled for it in the waste hood.

Waste Solvents: Two containers for waste solvents are provided, and reside in the waste hood. All organic solvents should be put in these containers when you discard them; do not pour them down the sink! If your solvent contains any chlorinated hydrocarbons, pour it in the chlorinated solvent container, otherwise, pour it in the non-chlorinated container. If you notice that one of the containers is full or almost full, inform your T.A.

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Laboratory Notebooks

A record of your experimental observations must be kept. The notebook must be of the bound type, (spiral notebooks are not allowed) with the pages numbered consecutively.

Leave the first few pages blank for an index. In your notebook, include all observations and any changes in the suggested procedure. Each page should be titled and dated. On the first page of an experiment, write out the key reactions together with molecular weights of important reagents and the quantities used. A drawing of the experimental apparatus should be included. Particularly important data to be recorded are weighings, volumes, color changes, durations, temperatures, difficulties encountered, measurements, and yields. TLC plates should be mounted in the book. Spectra and microanalytical report forms should be cross-referenced to the notebook page number.

The laboratory notebook is a practical device for recording procedures as they were done (not as they were planned to be done) and the <observations arising from the experiments. They should be terse. All data and calculations are to be recorded directly in the notebook in ink. Recording data on odd pieces of paper, to be later edited and transcribed, absolutely will not be tolerated. An erroneous result should be neatly crossed out and an explanation of the error inserted. Experimental difficulties should be noted along with possible ways to avoid them should the experiment be repeated. Conclusions derived from the experimental results should be noted, since these will be useful when writing the formal report. While a laboratory notebook is hardly supposed to be pretty, it is fair to say that is presentation is reflective of the scientific and organizational ability of its author.

Your notebook will be collected at the end of the semester, and graded as part of your laboratory technique evaluation.

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Laboratory Reports

Proficiency and ease in report writing are essential skills of every chemist. Many employers state that the greatest weakness of young chemists is their inability to report clearly the important results and conclusions of their work. This weakness frequently results from a combination of poor grammar, weak logic, and lack of precision, but most often from carelessness.

The importance of learning never to allow a carelessly written letter, technical paper, or report to leave your possession cannot be overemphasized. The greater part of your contacts with others in your career will come through the written medium rather than through personal contacts. Frequently your colleagues and superiors will know nothing more of your character and ability than what they can deduce from your correspondence and reports. Your ability is of little value if you cannot transmit what you have learned to others; good work poorly presented loses its force. The most successful chemists are not only intellectually and technically proficient, but also are able to write competently, thoroughly, and effectively.

The laboratory reports in this course are to be written in a format suitable for submission to a professional chemical journal. The following description of the format is an abbreviated version of "Instructions to Authors" that appears in the first issue each year of the Journal of the American Chemical Society. While no pretense is made that the format described below is the only acceptable form, we ask you to follow it. This may seem arbitrary, but remember that in the "real world" your reports often must conform with the ideas of others and not your own. Failure to follow the directions presented here will result in down-grading of the report regardless of its technical excellence.

The purpose of your lab reports is to convey information to your readers, and convince them to accept your observations and conclusions. Be concise and factual. Have your observations and conclusions in mind before you begin writing, and aim the whole report at presenting your results in a convincing manner. Reports should be written with a particular emphasis on clarity.


Format

Organization. The reports will consist of the following sections in order:

1. Title page (1 page)
2. Abstract (1-2 paragraphs)
3. Introduction (1-2 paragraphs)
4. Results
5. Discussion
6. Experimental Section
7. References (5 minimum)
8. Tables
9. Figures
10. Supplementary Material (original spectra and microanalysis forms)
11. Samples (submit in screw-cap vials, or sealed ampules if air-sensitive)

General Instructions. The reports must be submitted via e-mail using one of the common word processing programs (such as MicrosoftWord). Corrections on writing style, grammar, etc. will be made and the report may be resubmitted. Turn in one copy of the supplementary material to the TA in your laboratory section. The nomenclature used should be consistent, clear, unambiguous, and follow currently accepted IUPAC guidelines; see "Nomenclature of Inorganic Chemistry, Definitive Rules, 1970" Butterworths: London, 1971. Registered trademarks should be capitalized (e.g., Teflon, Pyrex), while other chemical names should be uncapitalized. Metric units (SI) should be used whenever possible.

Abstract. This section should summarize your principal results. Be specific! Briefly describe exactly what compounds you made, how you made them, and what the spectroscopic characterization told you about the chemical nature of the compounds. Recommendations for changes in the procedure based on your observations may be included.

Introduction. Introductions should contain only enough background material to show why the work is important. Briefly describe the general method used to synthesize the compound concerned, as well as methods previously employed. Relevant literature references should be cited. Usually it is a good idea for the first few references in your report to be books or review articles on the general area of chemistry under discussion; these citations should be followed by references to specialized literature articles more directly related to your work.

Results. Present facts concerning the compounds synthesized. This is conveniently organized around balanced equations for each step of the synthesis. Describe the procedure used to prepare and isolate each compound. Do not go into details about the procedure unless there is something unusual or noteworthy about it. For example, crystallization solvents are not usually discussed. Describe amounts of reagents used in terms of molar ratios or molar equivalents, rather than in grams or moles. Include a physical description of the material (gas, liquid, solid, color, viscosity, odor, crystallinity, air-sensitivity), a summary of physical data used to characterize the compound (m.p., b.p., elemental analysis, vapor pressure, IR, NMR, EPR, UV-Vis, mass spectrum), and a comparison of your data with analogus data in the literature. Merely listing your data and literature values is not sufficient; thoughtful interpretation must be included.

Discussion. This section may be combined with Results under the same heading, but descriptions of results and discussions should not be intermingled in the same paragraph. The discussion should present opinions concerning the work presented. These may include discussion of the yield or quality of the product, agreement or discrepancy between data you obtained and literature results, and suggestions for improvement in the written description or actual performance of the experimental procedure.

Experimental Section. Experimental results should be clearly and logically presented under separate subheadings. The first paragraph should contain statements as to the techniques employed, the sources of starting materials, and the equipment used. At the beginning of each synthetic procedure, the full name of the compound being prepared in that step should appear as the first line of the paragraph.

Analyses. Analyses should be reported in the following format in the Experimental Section after the yield: Anal. (C18H30P2Ti). Calcd: C, 60.7; H, 8.4; P, 16.6. Found: C, 60.2; H, 8.3; P, 17.2. Note that the percentage sign is not written. Analyses should be discussed in the text only if necessary; + 0.4% is "acceptable". Your microanalysis forms must be turned in with the report in the Supplementary Material. Along with your report, be sure to turn in your samples in screw-cap vials or in sealed tubes if air-sensitive.

Spectra and Spectroscopic Results. Spectroscopic results must be reported in full in the Experimental Section after the analytical results and the melting point if any. IR spectra should include the location of the band in cm-1, and its relative strength (s = strong, m = medium, w = weak); shoulders are indicated by sh. Thus: IR(Nujol): 2100(s), 2096(sh), 1870(w) cm-1. If your spectrum was taken in solution or as a Nujol mull, you should specify this but you should not report the solvent or Nujol peaks in your list. NMR spectra should include solvent, temperature, reference used (e.g., TMS), chemical shifts in d units, the multiplicity of the peak, magnitude of coupling constants (if any) in Hz, and the assignment. Thus: ¹H NMR (CDCl₃, 25 deg C): d 5.29 (t, J_PH = 6.0 Hz, PMe). UV-Vis spectra should include the solvent, temperature, and the positions of the peak maxima in nm. Thus: UV-Vis (toluene, 25 deg C): 470 nm. Original spectra must be included in the Supplementary Material.

References. References to the literature should be numbered in one consecutive series, repetition of references being avoided by using the superscript number corresponding to the original reference. Reference numbers in the text should appear as unparenthesized superscripts, but enclosed in parentheses in the collected references following the text. Literature references should be arranged and punctuated as shown:

(1) Doe, J. S.; Smith, J.; Roe, P. J. Am. Chem. Soc. 1986, 108, 8234-8265.

(2) Smith, A. B. Textbook of Inorganic Chemistry; Academic: New York, 1986; pp 123-126.

Inclusive pagination is required. Some references can be comments; there should be no footnotes on the pages where the text of the report is presented.The journal abbreviations that should be used are given in the first issue of each year in the Journal of the Chemical Society, Dalton Transactions and also in the reference text Chemical Abstracts Service Source Index (CASSI) (see the library).

Tables. One of your tables must be a comparison of your results with literature values. Otherwise, tables should be used only in case they will present information more effectively than running text. The column heads should be made as brief as possible, using abbreviations liberally. Lines of data should not be numbered unless these numbers are needed for reference in the text. Columns should not be used to contain only one or two entries, nor should the same entry be repeated numerous times consecutively. Data should not be included in one column which are deducible easily by simple arithmetic from data in another column.

Figures and Graphs. These should be carefully prepared line drawings on plain white paper or coordinate paper. Symbols (use open or closed circles, triangles, squares; do not use unusual representations) and lettering should be neat and legible. Figures should be numbered in series with a caption describing the content beneath the figure. Figures that depict spectra must have a caption that includes the experimental conditions, i.e., solvent, temperature, and units for the x and y axes.

Formulas and Equations. Empirical and structural formulas and mathematical and chemical equations should be written with care, paying particular attention to subscripts, superscripts, electric charges, and the placing of single and multiple bond lines. Electric charges should be written as + and -. Phenyl groups should be shown as C₆H₅ or Ph. Other groups may be abbreviated: methyl (Me), ethyl (Et), n-propyl (n-Pr), iso-propyl (i-Pr), butyl (Bu), cyclopentadienyl (Cp), etc. Unusual abbreviations must be clearly defined upon their first occurrence in the report.

Supplementary Material. This is an appendix, separate from your report, which includes originals of all the spectra you obtained and the microanalysis forms. You can also show the details of simple calculations which are discussed in the report (for example, d-spacings from X-ray powder diffraction data).

Style. Describe what you did in past tense; non-time dependent properties can be put in present tense. Use complete sentences, check spelling, and proofread! Slang, such as lab, prep, rotovapped, pumped dry, etc., should be avoided. Distinguish between "spectrum" and its plural "spectra". Also, note that it is slang to say "the IR was recorded," rather "the IR spectrum was recorded." Use direct, rather than indirect sentences.

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Guide to Chemical Abstracts and Science Citation Index

I. Chemical Abstracts


A. General Information


1. Published since 1907.

2. Currently the major abstracting journal covering the complete field of chemistry.

3. The abstracts are divided into 80 categories.

4. Information provided in the abstract:


a. Title of article.
b. Author(s) of article.
c. Affiliation of the first author.
d. Journal title, in abbreviated form.
e. Journal volume number, issue number, and inclusive paging of article.
f. Language of the article.
g. Abstract of the paper. May include structural diagrams.
h. Number of references if the article is a review.


5. Abstract numbers.


a. From 1907-1966 the indexes refer to column numbers (and then the position down the column): e.g., 2568g or 252163. Beginning with v.66 in 1967, the abstracts are numbered consecutively and the indexes refer to the abstract numbers.

b. Until recently, the abstract numbers in the indexes included a designation for review articles and patents. A review article was designated with a capital R before the abstract notation, e.g., R 2839, while a patent was designated in the indexes with a capital P, e.g. P 293840.


6. Indexes.


a. Current Issue Index:

1. This index occurs at the back of every issue and covers a two- week period.

2. The index includes a keyword index and an author index.


b. Volume Indexes:


1. Before 1962, covered one year period; since 1962, Volume Indexes are published twice a year, each covering a six-month period.


2. Volume Indexes include:

a. Author Index
b. Subject Index
c. Chemical Substances Index. Began with volume 76 (Jan.-June 1972)
d. Formula Index
e. Patent Number Index
f. Index of ring systems. Began with volume 67 (July- Dec. 1967).
g. HAIC Index (Hetero-Atom-in-Context). Also began with vol. 67.


3. Volume Indexes are published quite long after the volume is complete.


c. Cumulative Indexes:


1. Originally covered ten-year periods (1907-1916, 1917-1926, 1927-1936, 1937-1946, 1947-1956).

2. Now cover five-year periods (1957-1961, 1962-1966, 1967-1971, 1972-1976, 1977-1981, 1982-1986, 1987-1991).

3. Contains same sub-indexes as Volume Indexes above.


B. How to use the indexes.


1. General Comments.


a. Order in which to use the indexes. Unless there are extenuating circumstances, it is a good idea to start with the most recent Cumulative Index and work back.

b. Whenever possible use the Cumulative Indexes rather than the Volume Indexes. Similarly, use the Volume Indexes rather than the Keyword Indexes in the individual issues. This is a good strategy for two reasons:


1. You can cover more years and/or months in one place.

2. Mistakes made in the Issue Indexes are corrected in subsequent indexes.


c. The two most useful places to start are the Chemical Substances Index (or Subject Index) and the Formula Index. Some compounds that are listed in the Subject Index are not represented in the Formula Index because it is more complete. If the compound cannot be found under its name in the Subject Index, go to the Formula Index to find the name used by CA. Once the CA-preferred name is found, then recheck the Subject Index under that name.


2. Author Index (self-explanatory).

3. Subject Index (and Chemical Substances Index).


a. Since Jan. 1972, the Subject Index has been divided into the Chemical Substances Index, which contains all specific chemical compounds, and the General Subject Index, which contains classes of compounds, reactions, and applications.

b. In general, CA is most useful for information about specific compounds. It is not a very good place to go for information about reactions. Reactions of specific compounds are only listed under the name of the compound.

c. CA may on occasion be worthwhile to start with because you can locate review articles. However, you often get too many references and are faced with the problem of checking many abstracts and articles, often in obscure foreign publications.

d. Cross references. "See" references and "see also" references were provided in the Subject Index until July 1968.

e. Index Guide


1. Since July 1968, cross references and scope notes formerly provided in the Subject Index are now collected in the Index Guide.

2. Very useful place to check for the best subject headings to use, and to be certain that you have identified all the pertinent headings.


4. Formula Index


a. Uses the Hill system for arranging the molecular formulas: carbon, then hydrogen, then other elements alphabetically.

b. Under each molecular formula, the names of the compounds and their prefixes are arranged alphabetically.

c. Isomers are distinguished from each other by the alphabetical modifications (ie: cis, trans, etc.).

d. Gives the abstract number for some of the articles that deal with the compound. However, the listing of relevant abstract numbers is not necessarily complete in this Index. For example, articles dealing with related concepts, e.g., its function as a catalyst, may be found only in the Subject Index or Chemical Substances Index.

e. Best source of CA-preferred name needed to search the Subject Index and Chemical Substances Index. Nomenclature practices change from time-to-time and the CA-preferred name may change. Often there is not a "see" reference to the new name in the Subject Index. Then, you can either try various possibilities in the Subject Index or go back to the Formula Index for the new (or old) name, as the case may be.


5. Patent Index.

6. Index of ring systems. (There is a short introduction in the front of this Index which can be consulted.)


a. Based on the skeletal structure of the ring system.

b. Provides the CA-preferred name; then can go to the Subject Index.

c. No abstract numbers are given in this Index.

d. Includes all ring systems for which entries are found in the Subject Index.

e. Arrangement:


1. First by the number of rings in the system.

2. Then by the ring size, in increasing size.

monocyclic

3-membered ring
4,
5, etc.

bicyclic

3,3
3,4
3,5 etc.
4,4
4,5 etc.
5,5 etc.


3. Within each ring-size group, the compound molecular formulas are arranged by the Hill system.

4. Then, the ring system names are arranged alphabetically.


7. HAIC (Hetero-Atom-In-Context) Index


a. A computer-produced index which spotlights each element in the molecular formula, except for C and H. This index is good for metals, too.

b. Includes all molecular formulas found in the corresponding Formula Index, except hydrocarbons.

c. Designed to supplement the Formula Index by providing access points for each element, except C and H.

d. Because the HAIC Index spotlights the element in the context of the molecular formula according to the Hill System (which is the way in which the Formula Index is arranged), one then has the exact information needed to go to the Formula Index or Subject Index.

e. No abstract numbers are given in this Index.


8. CASSI (Chemical Abstracts Service Source Index)


a. Successor to the CA List of Periodicals. This index is useful for finding out what the full title of a journal is from an abbreviated title.

b. Main volume was published in Dec. 1968. Quarterly supplements and one annual cumulation have appeared since then.

c. A new abbreviation standard was adopted for periodical title words beginning in Jan. 1967. May find it useful to check older Lists of Periodicals if references are older than Jan. 1967 and cannot be located in CASSI.


II. Science Citation Index


A. General Information


1. Published by the Institute for Scientific Information in Philadelphia.

2. Published since 1964, although the coverage was quite limited in 1964.

3. Enables users to go from a specific article and work forward. In other words, it enables the user to find out who has cited an article in a footnote or bibliography since the original article was written.
This is the only index which allows this forward checking. All other indexes only enable the user to find out what was published previously.

4. Published quarterly, with cumulated annual volumes.

5. Divided into 2 parts:


a. Source Index volumes.

b. Citation Index volumes.


6. Production of the Science Citation Index.


a. When a journal issue arrives at the Institute, each article in the newly-received journal issue becomes a Source Document and goes into the Source Index.
b. All the references from the footnotes and bibliography taken from the article go into the Citation Index. These references, of course, can be from any year. Thus, one can look up an article from any year in any issue of SCI after its publication date to see if it has been cited.


7. Advantages.


a. In most cases it is reasonable to assume that the references cited in a given article are related to the subject and would therefore interest you.
b. Avoids having to deal with terminology or nomenclature ambiquities.
c. Covers an entire journal issue, almost cover-to-cover. (CA covers quite a few journals selectively and only abstracts articles.) SCI covers notes, discussions, letters, criticisms, corrections, etc., which can be quite useful.
d. Can use the Source Index as a fast way to locate articles by a given author, especially for the current year. (SCI has fewer issues to check in the current year than does CA.)


8. Disadvantages.


a. Dependent upon the author of the article to make appropriate choices of articles to cite.
b. Some cited articles are of only peripheral interest in relation to the main subject of the article.
c. Can only look in the Citation Index under the name of the 1st author of the paper.


B. How to use the index.


1. To use, start with a key paper (or whatever articles have been determined as worthwhile) and check in the Citation Index under the first author's name to see who has cited that paper since it was published. For further details, see next page.

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316/404 Index	News	Lecture Notes	Experiments