Chem 36H Lab Lecture

1. Chem 36H Lab Lecture Agenda: Review of Team Project Searching J. Chem. Ed. Online Review of ACS-Style Reports 4. Tour the PAMS Library Website with Nan Butkovich

2. The Team Project Self-selected teams of 2-3 students Components: 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

3. 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 Synthesis: • Describe route in written form • Scheme of route with compounds numbered • Type of analyses to be run • References Include photocopies of all pertinent reference material

4. Activities for Team Project Get Team Project Proposal approved by me & TA Order chemicals (if not in inventory); due date is March 28/29! Start the project in April or beforehand (with TA’s approval) Submit one copy of the Final Report to your TA Present a poster at end of semester. Dress code is business casual.

5. J. Chem. Ed. Online Link: http://jchemed.chem.wisc.edu/ 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

6. Other Useful Links Access the Chem 431W website: http://courses.chem.psu.edu/chem431 Useful Links: • ACS Journals • NIST • Japenese NIMR/SDBS • PAMS Library

7. ACS-Style Final Reports Sections of a Final Report: Title Byline and Affiliation Abstract Introduction Results & Discussion Conclusions Experimental Section Acknowledgments References Supporting Information Do not use the first person singular; use the passive voice. Use past tense.

8. The Title • Purpose: • Attract the potential audience • 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.

9. Byline and Affiliation • Byline: • 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 Affiliation: • Refers to the institution, address, and contact information e.g. Department of Chemistry, The Pennsylvania State University, University Park, PA 16802 kmasters@psu.edu (note text is italicized) Ref: The ACS Style Guide, 2nd ed.

10. Abstract • Purpose & Features: • States the problem or the purpose of the work • Mention the name of the compounds synthesized and method used to make • it • 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.

11. Abstract • 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.

12. Introduction • Purpose & Features: • To clearly state the work and reason for doing it • To provide a concise background discussion of the work, the significance • and scope of the work, and the limits of the work • To outline what has been done previously (cite pertinent literature) • 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.

13. Introduction • 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 hypothesis. • - 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.

14. 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.

15. 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 discrepancies. • 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? Why? • - What could have been done differently to improve results (yield, % ee, purity, etc.)? • Brief conclusion with importance of experiment and results

16. Conclusions • 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.

17. Conclusions • 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 study.

18. Experimental • 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 information). • 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.

19. Experimental First paragraph: General Information Example: 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.

20. Experimental • Entries for individual synthesized compounds. Tetra(2-aminoethyl)methane (1) A solution of 3,3-bis(2-azidoethyl)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

21. Acknowledgments 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

22. References • 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 #.

23. 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 accordingly. • 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.