Lab Lecture (March 6/7)

Chem 36H Lab Lecture
1. Review of Team Project
2. Searching J. Chem. Ed. Online
3. Review of ACS-Style Reports
4. Tour the PAMS Library Website with Nan Butkovich
The Team Project
Self-selected teams of 2-3 students
1. Team Project Proposal:
To be graded by me and your TA
2. Experimental outline
3. Team Synthesis:
Synthetic Route (2 to 3 steps)
Analysis of intermediates and final product
ACS-style report
4. Team Poster Presentation:
Guidelines are posted on the web
Poster Symposium on Wednesday, May 2nd, 5 to 7 pm
Team Project Proposal
1. Introduction:
• Relevance/significance of reaction(s) and/or final product
• Structural features of compound
• Show figure of compound to be synthesized
2. The
Describe route in written form
Scheme of route with compounds numbered
Type of analyses to be run
3. References
Include photocopies of all pertinent reference material
Activities for Team Project
1. Get Team Project Proposal approved by me & TA
2. Order chemicals (if not in inventory); due date is March
3. Start the project in April or beforehand (with TA’s
4. Submit one copy of the Final Report to your TA
5. Present a poster at end of semester. Dress code is
business casual.
J. Chem. Ed. Online
Tips for using website:
• Search current issue or previous issues: “In the
Laboratory” section
Search JCE Index - title or keyword search
Downloand and print article AND supplemental information
Other Useful Links
Access the Chem 431W website:
Useful Links:
ACS Journals
Japenese NIMR/SDBS
PAMS Library
ACS-Style Final Reports
Sections of a Final Report:
Byline and Affiliation
Results & Discussion
Experimental Section
Supporting Information
Do not use the first person singular; use the passive voice.
Use past tense.
The Title
1. Attract the potential audience
2. Aid retrieval and indexing
Tips for the Title:
• Reflect the report’s content and emphasis
• Not too short (3 to 4 words), but not too long (14 to 15 words)
• Choose terms that are specific to the work
• Avoid jargon, formulas, symbols, and abbreviations
• Include several keywords
• Create the title after you’ve written the report/paper
Ref: The ACS Style Guide, 2nd ed.
Byline and Affiliation
• Authors’ names
• Includes all people who made a contribution to the work
• Be consistent with the format you use:
e.g. Katherine M. Masters, Kim C. Earnheart
e.g. K. M. Masters, K. Earnheart
• Refers to the institution, address, and contact information
e.g. Department of Chemistry, The Pennsylvania State University,
University Park, PA 16802
[email protected]
(note text is italicized)
Ref: The ACS Style Guide, 2nd ed.
Purpose & Features:
• States the problem or the purpose of the work
• Mention the name of the compounds synthesized and method used
to make
• Summarizes principal findings
• Points out major conclusions
• Helps reader determine the nature and scope of report/paper
• Concise and self-contained
• Typically, one paragraph; usually between 80 to 200 words
• Include key features of work
Write the abstract after you have written the report.
Ref: The ACS Style Guide, 2nd ed.
One sentence each:
- State significance of research.
- Identify compounds synthesized from starting material
(name both!), % yield, % ee (if applicable).
- Compare yield/purity to literature values.
Include a structure diagram of product or brief reaction diagram.
Purpose & Features:
To clearly state the work and reason for doing it
To provide a concise background discussion of the work, the
and scope of the work, and the limits of the work
To outline what has been done previously (cite pertinent
To demonstrate the continuity of previous work to yours
Often one to two paragraphs long
Include a structure of the product you synthesized
May include a mechanism if known
Ref: The ACS Style Guide, 2nd ed.
Broad significance of field; general introduction of topic
e.g. Chiral chemistry
Specific significance of the compounds/reactions studied;
importance of topic
- e.g. Stereospecific dihydroxylation of alkenes
Description of reaction & mechanism
Use general terms, but identify compounds involved in
reaction and their roles.
If reaction mechanism is unknown or disputed, include a
- Comparison of reaction chosen to alternative methods
State why method was chosen (i.e. reagent availability/cost,
yield, etc.)
If you are performing a “demonstration of principles” experiment,
discuss an application of the principle.
Results & Discussion
Summarize data
Tabulate data, if appropriate
Use figures and schemes
Interpret and compare results
Point out features and limitation of the work
Relate your results to current knowledge in the field and
to the original
purpose of the work
Point out key spectral data
Ref: The ACS Style Guide, 2nd ed.
Results & Discussion
Summary of products obtained
- % yield, % ee (if applicable)
- Comparison to reported literature values
Summary of characterization methods performed
Spectral interpretation
- Discuss key identifying features. Do not spend pages
explaining every peak in each spectrum. For example, if an
acetyl group is added, note that peak and any changed by its
addition (and propose why those changed). There is no need
to repeat analysis of unchanged peaks.
- Identify and explain origins of impurities.
- Compare your results to literature spectra and explain any
Comments on synthesis
- What, if anything, was changed in progress of synthesis
compared to your literature source?
- Was yield low/high compared to the reported literature value?
- What could have been done differently to improve results
(yield, % ee, purity, etc.)?
Brief conclusion with importance of experiment and results
Purpose: To put the interpretation into the context of the
original problem or purpose
Do not repeat discussion points
Include possible future studies, propose ways to improve
yields, etc
Ref: The ACS Style Guide, 2nd ed.
Summarize major findings
Product(s) formed, % yield, % ee
Successful improvements to literature procedure
Discuss future directions
What would you do to more broadly apply the
chemistry learned in this experiment?
Include a concrete next step for investigation, including a new
compound or substrate, and briefly state why it is important to
Two Parts
General Methods
- List all reagents and solvents. Include manufacturer,
purity, and any preparation before use. If reagents
were used as received, say so.
- Instrumentation: List all instruments used, including
manufacturer and model number (see Chapter 3 for this
Synthetic Procedure and Characterization Data
- For each compound, include IR and 1H, and 13C NMR
spectral analysis. For solid compounds, include the
melting point data. These are REQUIRED. If you have
trouble getting these spectra, consult with the course
instructor or a TA.
Include any other characterization data, such as optical rotation,
MS, additional NMR nuclei, etc.
First paragraph: General Information
All reagents and solvents were purchased from Aldrich Chemical Co.
(Milwaukee, WI). Acetic anhydride was distilled under N2; all other
chemicals were used as purchased. All NMR spectra were run on a
400 MHz Bruker spectrometer. Infrared spectra were taken on a
Mattson GL-4020 FT-IR spectrometer. UV/Vis spectra were obtained
on a Hewlett-Packard 8452A diode array spectrophotometer.
Entries for individual synthesized compounds.
Tetra(2-aminoethyl)methane (1) A solution of 3,3-bis(2azidoethyl)pentane-1,5-diazide (9) (160 mg, 0.55 mmol) in 5 mL of
absolute ethanol was combined with 10% palladium on carbon (16
mg, 0.1 mmol) in a hydrogenation vessel. The reaction mixture was
hydrogenated at 40 psi hydrogen pressure at room temperature for
24 h. The suspension was filtered through Celite, and the filtrate
was concentrated and dried in vacuo to give 94 mg of 1 as a
viscous yellow oil (91%): IR (neat) 3295, 3385 cm-1; 1H NMR (200
MHz, CD3OD)  1.39 (t, 8H), 2.63 (m, 8H); 13C NMR (50 MHz,
CD3OD)  36.9, 37.2, 41.2; MS (CI) m/z (relative intensity) 189
(MH+, 16); HRMS calcd for C9H24N4 189.2079, found 189.2086.
Note: Numbers of compounds & use of ()
Ref: J. Org. Chem. 1999, 64, 8945
Purpose: To recognize those persons who assisted
with the work, gave advice, provided funding, or
provided equipment.
Examples: Your TA, me :)
Michele Brown & Linda Price
Dr. Bortiatynski
Use ACS format. See ACS Style Guide for details.
You will need at least 2-3 references to accomplish the proper
scope of the introduction. Cite peer-reviewed sources (journals,
books) wherever possible.
You DO NOT need to cite your laboratory notebook like you did in
Chem 14/15.
Example: Nicolaou, K. C. J. Org. Chem. 2005, 70, 7007.
Author’s name(s) Journal Title Abbrev. Year, Volume, Page #.
Supporting Information
- All annotated spectra, which must be labeled with the compound
structure. Refer to these spectra as figures in the text and number them
- Notebook pages: A colleague should be able to reproduce your
experiments reasonably from your notes. Be careful of significant
figures when recording masses during the experiment.
- Graded experimental outline.
- ALL referenced materials. If a referenced book is not available on the
course library shelf, a photocopy of the relevant pages must be included.
For particularly long references (>15 pages), speak with the grading TA
about his/her requirements.