Chem 2312

Chemistry 2312H
Instructor: Thomas R. Hoye
Fall 2024
Honors Organic Chemistry Laboratory (5 cr)

Nearly all files are PDFs (active links are blue; files to be added later are white)

SYLLABUS Chem 2312, Fall 2024
HANDOUTS
- Synopsis of Experiments #1-5 and Lab Report Due Dates (posted 8-28-24)
- Lab Check-in Times and Round One (Week #1) Tutorial Schedules (posted 8-31-24)
- Lab-open hours for Fall 2024 (posted 9-3-24)
- Lab Notebook and Report Guidelines (posted 9-5-24)
- NMR Data Retrieval and MNova Installation Instructions (posted 9-3-24)
- MNova Installation Instructions for Mac (posted on 8-30-24)
- MNova Installation Instructions for PC (posted 8-30-24)
- Zip file of the 1H NMR spectrum of 3-chloroacetophenone (posted 8-30-24)
- Zip file of the 13C NMR spectrum of 3-chloroacetophenone(posted 8-30-24)
- Properties of Common Organic Solvents, ranked by polarity (posted 9-5-24)
- Hazardous (and non-Hazardous) Waste Handling Guidelines (posted 9-7-24)
- YouTube Videos for NMR, IR, and MS (posted 9-7-24)
- Instructions for installing Citrix Receiver (for Apps To Go) for accessing IRTutor, ChemDraw, and Chem 3D applications (posted 9-10-24)
- Links to Technique Videos by Prof. Jane Wissinger (posted 8-24-24)
- Flash column chromatography guidelines (posted 9-10-24)
- Link to "Video: Mini-lab tour for undergraduate organic labs" at the Departmental NMR lab website (posted 9-10-24)
- NMR Spectroscopy Tutorial (website from the Khan Academy; posted 9-10-24)
- Infrared Spectroscopy Theory (PDF from U Colorado; posted 9-7-24)
- 9-12-24 (Zoom) Recording of Lecture (while TRH had COVID): IR examples in IRTutor, simple NMR concepts using chlorinated ethanes from SDBS and 3-nitroacetophenone using MNova (posted 9-12-24)
- Zip folder of the .mnova worked up 1H NMR spectrum of 3-nitroacetophenone that I worked through in this recorded lecture (posted 9-12-24)
- Round Two (Weeks 3/4) Tutorial Schedule master (not done in 2024)
- Short video on the the Ozonolysis Reaction apparatus (5 min, posted 9-18-24)
- Short video on the the Vacuum Distillation set-up (5 min, posted 9-18-24)
- Video of an MPLC Tutorial set-up (27 min, posted 9-20-24)
- You can access (larger) .mp4 versions of the above three .mov tutorial videos at this link (posted 9-20-24)
- Ozone Generator Instructions (posted 09-17-24)
- Spectroscopies Worksheet #1 (posted 9-24-24)
- Epoxyphenoxypropane-161014 NMR Zipped Folder (posted 9-26-23)
- Benzyl glycidyl ether-161014 NMR Zipped Folder (posted 9-26-23)
- Updated Vacuum Distillation Instructions for Aspirator Vacuum Source (posted 10-1-24)
- Coupling Constant Analysis; J. Org. Chem. 2002, 67, 4014–4016 (posted 10-2-24)
- Coupling Constant Analysis: PPoint lecture on 10-3-24 (posted 10-2-24)
- X-ray structure .pdb file of the atomic co-ordinates of the amide structure (posted 10-17-24): see Experiment #3 for instructions on how to view (via iCn3D, on a web browser)
- Zip file of the 1H NMR spectrum of a bromofluorotoluene (of a different substitution pattern of your 10) (posted 10-8-24)
- Zip file of the 13C NMR spectrum of the same bromofluorotoluene (of a different substitution pattern of your 10) (posted 10-8-24)
- Slide clip from Mosher Ester discussed in class 10-22-24 (posted 10-21-24)
- Nature Protocols Mosher Ester publication (posted 10-21-24)
- space
- Notes on Computing Menthone Equilibrium Values (posted 11-14-24)
- Template (a 2 page PDF) for Creating Your Excel Spreadsheet for the Menthone Boltzmann Equilibrium Values (posted 11-14-24)
- Excel file of the DFT energies for the conformations of the trans- and cis-menthones (posted 11-13-24)
- Zip file of two folders: cis-Menthone PDBs and cis-Menthone PNGs from PDBs (posted 11-13-24)
- Zip file of two folders: trans-Menthone PDBs and trans-Menthone PNGs from PDBs (posted 11-14-24)
- The Boltzmann Exercise to be Handed in Tue. Dec. 3 (posted 11-14-24)
- space
- Instructions for Accessing Maestro at MSI via Open OnDemand (a Linux desktop emulator) (posted 9-26-23; not done in 2024 because MSI has no Schrodinger license)
- MNova file of the 1H NMR spectrum of your starting material 10 in C6D6 (posted 10-??-??)
- Coll Czech Chem Comm '89 151-159 (posted 10-7-21)
- Spectroscopies Worksheet #2 -- OPTIONAL (posted 11-4-22)
- MNova file of isomenthone 1D and 2D spectra (posted 11-4-22)
- 2312 Report Grading Rubric Guidelines (posted 10-29-23)
- "Peer-TA Advice" for Reports and Experiments 3-5 (posted 10-29-23)
- Brief Introduction to 2D NMR Spectroscopy (posted 10-29-23)
EXPERIMENTS
- Exp 1. Ketone Reduction (posted 9-5-24)
- Updated Exp 2. Ozonolysis (of beta-Pinene) and Hydrogenation (of Pulegone) (posted 10-1-24)
- Exp 3. Ester Enolate Alkylation/Saponification/DCC Amide Coupling (update posted 10-15-24)
- Exp 4. Palladium Coupling, Lipase Kinetic Resolution, Mosher Ester Analysis (posted 10-8-24)
- Exp 5. Diels-Alder Reaction, Luche Reduction, and Photochemical 2+2 Cycloaddition (posted 10-3-24)
- Staggerred Schedule for Experiments 3-5 (posted on 10-8-24)
- Team Assignments for Mosher Ester Analysis (Experiment 4, posted on 10-18-22) not relevant for 2023
ZOOM RECORDINGS
Zoom Recording from ad hoc lecture on Saturday 9-11-21
Zoom Recording (1 of 2) from ad hoc lecture on Saturday 9-18-21
Zoom Recording (2 of 2) from ad hoc lecture on Saturday 9-18-21
iPAD NOTES TO ACCOMPANY ANY ZOOM RECORDINGS
iPad Notes from ad hoc lecture on 9-11-21
9-7-24 Ad Hoc Lecture Recorded on Zoom (not posted; sent to two who could not make it because of 11 am football game (EMT and Band)
MNova file of the 1H NMR spectrum of "Y" in DMSO-d6 (posted 10-6-22)

Schedule of Times for your Access to the Ozone Generator (posted 09-25-20) Not needed in F'21 or F'22 or F'23

The Hoye Group at the University of Minnesota