Home Page: Taber home page.

Chem 333
Department of Chemistry and Biochemistry
University of Delaware

Organic Chemistry Lab

Office Hours: 202 LDL     W 3:00-4:00, F 3:00-4:00

            Work phone #: 831-2433     


Tutors are also available. I will not talk with you about the course on the day of the exam. I can be reached at Douglass F. Taber

Texts: Organic Chemistry Laboratory, Bell, Clark, Taber and Rodig ISBN: 0-03-029272-7 (lab)

Molecular Model Set

Lab Lecture Text: Organic Spectroscopic Structure Determination Taber ISBN: 978-0-19-531470-0

Important!: Locate the errors in this text, which can be found at (Errata), and correct them in your copy.

You will use the Worksheet with every problem that you solve. This can be found at (Worksheet). It would be a good idea to print out a few.

This course is designed to be self-paced. If you have time early in the semester, or even before it begins, you can work through Chapter One of the lab lecture text on your own. For detailed help on each problem, go to (SpecBook). Once you get into them, the problems become puzzles that are fun to solve.

Grading: There will be four hour exams, 3:35-4:30 For those only taking the lab lecture, your grade will be based on these exams, 25% each. If you cannot be present for the exam, you may make it up ahead of time only. If you are sick the day of the exam, send me an email before the exam. Your grade for the exam will be the average of your grades for the other three exams. If you choose to take the exam anyway, your grade will be that same average, or the grade you earn, whichever is higher. If you are taking both the lab lecture and the lab, the lab lecture exams will constitute 60% of your grade. The rest of your grade will be lab quizzes 20%, and lab book, including results, 20%. You will turn in your notebook at the end of each lab period. Your TA will grade it and return it to you promptly.

2010 exams:

2010 exam #1, 2010 exam #2, 2010 exam #3, 2010 exam #4.

2010 exam answers:

2010 exam #1 answers, 2010 exam #2 answers, 2010 exam #3 answers, 2010 exam #4 answers.

2011 exams:

2011 exam #1, 2011 exam #2, 2011 exam #3, 2011 exam #4.

2011 exam answers:

2011 exam #1 answers, 2011 exam #2 answers, 2011 exam #3 answers, 2011 exam #4 answers.

2012 exams:

2012 exam #1, 2012 exam #2, 2012 exam #3, 2012 exam #4.

2012 exam answers:

2012 exam #1 answers, 2012 exam #2 answers, 2012 exam #3 answers, 2012 exam #4 answers.

Handouts: Handouts as needed to supplement the text will be posted on the course Web site.

Lab Lecture Schedule: The class each day will be held in two parts, 3:35-4:30, and 4:35-5:30, in 101 BRL When the schedule indicates that we will be working on problems, we will be practicing strategies and answering questions. No new lecture material will be presented.

Sep. 10th 13C NMR ..... 13C NMR

Sep. 17th 13C NMR ..... Problems 1-15

Sep. 24th 13C NMR ..... Problems 1-15

Oct. 1st Exam #1 ..... 1H NMR

Oct. 8th 1H NMR ..... Problems 16-34

Oct. 15th IR ..... Problems 16-34

Oct. 22nd Exam #2 ..... Alkenes, Arenes

Oct. 29th Alkenes, Arenes ..... Problems 35-50

Nov 5th UV quantitative ....., UV Practice

Nov 12th Exam #3 ..... , chemiluminescence

Nov 19th Mass spec ..... Problems 35-50

Nov 26th NOESY, COESY, HETCOR ..... Problems 35-50

Dec 3rd Exam #4 ..... two hours if you want

Organic Lab: Read the assignment, both the chapter in the text and the handout from the web. Come prepared! Goggles are required and must be worn at all times in the laboratory. Suitable clothing must also be worn. No open shoes or bare midriffs. Please read the lab schedule for November carefully, and follow it. Labs will meet Monday and Tuesday of Thanksgiving week, to make up for not meeting Monday and Tuesday the first week in November.


1 Week of Sept 10th: Check in, Crystallization Chapters 1, 2 and 3 (Crystallization)

2 Week of Sep 17th: Extraction Chapter 4 (Extraction)

3 Week of Sep 24th: Distillation and GC Chapters 5 and 6 (Distillation)

4 Week of Oct 1st: Chemical Database Searching (Databases). You should work on this from the beginning of the semester.

5 Week of Oct. 8th:Steam Distillation of Essential Oils (Essential Oils)

6 Week of Oct. 15th: Complete Week 5; HPLC and TLC of analgesics Chapters 8 and 9 (Analgesics)

7 Week of October 22nd: Cholesterol from egg yolk. Start with two hardboiled egg yolks, which you must bring to lab (Cholesterol)

8 Week of October 29th: Complete cholesterol. Start oxidation of 4-nitrobenzyl alcohol Chp 21C, F except use oxidation method of Tetrahedron Lett. 48:8839 (2007), starting with 300 mg of alcohol. After the oxidation is worked up, divide the extract into two equal parts. One of the halves should be concentrated and carried on to the Horner-Emmons reaction with DBU, following the procedure of Tetrahedron Lett. 51: 3297 (2010), except that the reaction should be heated for 20 min at 80o. The worked up product should be concentrated and purified by a silica gel chromotography column. Record the weight and melting point of the product ester. The other half of the worked up oxidation should be concentrated and purified by a silica gel chromotography column. Record the weight and melting point of the product aldehyde. Use a little of the product aldehyde to carry out 21F, just to observe the change by TLC.

9 Week of Nov. 7th: Complete oxidation. Note that this week begins with the Wednesday labs, and continues through Tues Nov 13th. Labs will not meet on Mon Nov 5th, nor on Tues Nov 6th, which is Election Day.

<10 Week of Nov. 14th: Grignard reaction Chapter 19 (Grignard) Note that this week begins on Nov. 14th and runs through Nov 20th

<10 Week of Nov. 26th: Finish Grignard reaction, clean up, check out