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CHEM 3381: Majors Laboratory for Organic Chemistry II

This lab course is for chemistry majors. Biochemistry majors are encouraged, but not required, to take this course. Non-chemistry majors can also take this course if they wish. This course meets twice a week and is worth 2 credit hours.

CHEM 3381 covers some of the same material as does CHEM 3341, as well as a Wittig reaction, a Grubbs metathesis, an aromatic multi-step synthesis lab that covers three lab periods, and synthesis of frambinone that uses aldol condensation and catalytic hydrogenation. CHEM 3381 also includes two independent projects: one week of natural product isolation, and three weeks of a synthesis project.

LabDayTimeLocationTA
410MW1:00 PM-3:50 PMEKLC M1B35Will Yi
451TR9:00 AM-11:50 AMEKLC M1B35Eric Miller
441TR1:00 PM-3:50 PMEKLC M1B35Thomas Carey

Experiment Schedule

Dates Experiment Bring Quiz Notes
Mon Aug 28 - Tue Aug 29 Lab check-in & NMR Review (nothing) No If you don't remember NMR from OChem 1, read up on it ahead of time. These sources are helpful:
Chapters 18 & 20 in the Lab Handbook and Chapter 13 in Loudon; Spectroscopy Tutorial and NMR Theory Tutorial on this web site.
The in-class Spectroscopy Worksheet, the Spectroscopy Homework, and the Practical NMR lab are not due as part of this lab, but they may be helpful.
Wed Aug 30 - Thu Aug 31 Exp. 31: Large-Scale Column Chromatography Prelab Yes (SQ Answers)
Mon Sep 4 - Tue Sep 5 No labs
Wed Sep 6 - Thu Sep 7 Exp. 32: Oxidation of a Diol Prelab Yes (SQ Answers)
Mon Sep 11 - Tue Sep 12 Exp. 23: Fischer Esterification Prelab Yes (SQ Answers) NMR spectra of all 5 esters. Note that these are for the methyl esters, not the ethyl esters, so you will have to keep this in mind when comparing your own spectra.
Wed Sep 13 - Thu Sep 14 Exp. 20: Wittig Reaction Prelab Yes (SQ Answers) You will need the Handbook supplements on Green Chemistry and NMR Coupling Constants.
During this experiment, you will prepare the reaction for Synthesis of Frambinone.
Mon Sep 18 - Tue Sep 19 Exp. 33: Coumarin Dyes Prelab Yes (SQ Answers)
Wed Sep 20 - Thu Sep 21 Exp. 34: Synthesis of Frambinone, day 1 Prelab Yes (SQ Answers) Rheosmin paper cited for first step
Mon Sep 25 - Tue Sep 26 Exp. 34: Synthesis of Frambinone, day 2 (nothing) No
Wed Sep 27 - Thu Sep 28 Exp. 14: Epoxidation of Cholesterol Prelab Yes (SQ Answers)
Mon Oct 2 - Tue Oct 3 Exp. 35: Nucleophilic Aromatic Substitution Prelab Yes (SQ Answers) You will need the Handbook supplement on Microwave-Assisted Chemistry.
Wed Oct 4 - Thu Oct 5 Exp. 36: Substitution Kinetics Prelab Yes (SQ Answers) You will need the calculations spreadsheet for this lab.
Mon Oct 9 - Tue Oct 10 Exp. 37: Alkyne Formation Prelab Yes (SQ Answers) During this experiment, you will also start selecting your project for the Multistep Synthesis Project (Exp. 40). Read this experiment in advance and bring a laptop if you have one.
Wed Oct 11 - Thu Oct 12 Exp. 38: Aromatic Multistep Synthesis, day 1 Prelab Yes (SQ Answers)
Mon Oct 16 - Tue Oct 17 Exp. 38: Aromatic Multistep Synthesis, day 2 (nothing) No The project proposal and materials request for the Multistep Synthesis Project are due.
Wed Oct 18 - Thu Oct 19 Exp. 38: Aromatic Multistep Synthesis, day 3 (nothing) No
Mon Oct 23 - Tue Oct 24 Exp. 15: Diels-Alder Reaction Prelab Yes (SQ Answers) NMR spectrum of the adduct. You will need the Handbook supplements on Green Chemistry and NMR Coupling Constants.
Wed Oct 25 - Thu Oct 26 Exp. 39: Halogenation of Alkanes Prelab Yes (SQ Answers)
Mon Oct 30 - Tue Oct 31 Exp. 40: Multistep Synthesis Project, day 1 Prelab No
Wed Nov 1 - Thu Nov 2 Exp. 40: Multistep Synthesis Project, day 2 (nothing) No
Mon Nov 6 - Tue Nov 7 Exp. 40: Multistep Synthesis Project, day 3 (nothing) No
Wed Nov 8 - Thu Nov 9 Exp. 40: Multistep Synthesis Project, day 4 (nothing) No
Mon Nov 13 - Tue Nov 14 Exp. 40: Multistep Synthesis Project, day 5 (nothing) No
Wed Nov 15 - Thu Nov 16 Exp. 40: Multistep Synthesis Project, day 6 (nothing) No
Mon Nov 20 - Fri Nov 24 No labs
Mon Nov 27 - Tue Nov 28 Exp. 40: Multistep Synthesis Project Presentations, day 1 (nothing) No
Wed Nov 29 - Thu Nov 30 Exp. 40: Multistep Synthesis Project Presentations, day 2 (nothing) No During this experiment, you will prepare the reaction for Grubbs Metathesis.
Mon Dec 4 - Tue Dec 5 Exp. 41: Grubbs Metathesis Prelab Yes (SQ Answers)
Wed Dec 6 - Thu Dec 7 Lab Check-out & Comprehensive Lab Quiz Buff Onecard Yes For the final quiz, you should review the study questions and prelab quizzes.