(Please consult http://photon.chem.temple.edu for revisions from any campus computer.)

CHEMISTRY 2214 (Majors) and 2924 (Honors)
Spring Semester 2013
Monday, 1:00-3:50 PM and Thursday, 12:30-3:20 BE401

Instructor: Mr. H. Gottlieb, BE126B, Telephone 215-204-1637; Facsimile 215-204-1532

e-mail: harry.gottlieb@temple.edu; Office Hours: Posted in Blackboard.


This course is a continuation of the first semester MAJORS (Chem 2213) and HONORS (Chem 2923) microscale laboratories. Either of those laboratories serve as prerequisite. Additional microscale laboratory techniques in Organic Chemistry are to be learned. As before, this course places emphasis on independent learning. Students are required to plan their experiments, manipulate equipment in order to separate, purify and characterize organic compounds and write reports after each project detailing their laboratory experience. Hands on use of spectroscopic (IR and NMR) and computational (Spartan and WebMO) tools are involved. Laptop computers are available for use in the laboratory.

The class meets for one session of two hours and fifty minutes each week.

Co-requisite: Chemistry 2292 - Honors Organic Chemistry Lecture OR Chemistry 2212 - Organic Chemistry Lecture for Majors It is presumed that most students will have completed the first semester of Honors Organic Chemistry, or the corresponding Organic Chemistry for Majors with the grade of C- or better. Regardless, however, some knowledge of stoichiometry including determination of limiting reagents, the preparation of solutions [molarity], and the use of balances for weighing purposes is assumed. Further, the use of the Spartan software, WebMO, and the IR and NMR equipment learned in the first term will be continued. The work this term places an emphasis on independent skills each student gains in carrying out synthesis and characterization of organic compounds.
Required textbook and supplementary materials: Additional material and reading matter will be placed on the server to be found at http://photon.chem.temple.edu and which can be accessed from any computer ON CAMPUS.


The FIRST LABORATORY DAY IS Thursday, 24 January 2013 .

Your Organic Chemistry laboratory is scheduled (in BE 401) for only one meeting per week. Students are expected to arrive on time. During the "wet-lab" portion of the course (vide infra), every student will bring with them a hard copy of the completed prelab write-up that can be downloaded from the Honors/Majors Section appearing on http:// photon.chem.temple.edu.

The completed laboratory report is due (by email) on or before noon of the third calendar day following the laboratory. You should also be prepared for the quiz that begins every lab.

Although there will a "catch-up-make-up" session scheduled for the "wet lab" portion of the course at the end of the term, there is no provision for a "make-up" of a missed quiz. As a result of an absence you will have lost the opportunity to accumulate points towards your final total and grade. So, when you return from an absence, come prepared to undertake the laboratory work as scheduled on the syllabus...not for what you missed!

You should plan now on having your "Safety Guidelines for CST Labs" and eye protection.


Thus, in addition to safety glasses (contact lenses are not to be worn as organic solvents getting between your iris and the lens can damage your eyes) you are also expected to wear sufficient clothing and foot protection so that dropped objects (flasks, pipettes,etc.) will not injure you and you will not be unprotected in the event of accidental spills.

As a general rule, laboratory coats must be worn. Temple University provides laboratory coats for student use.

Our earlier experiences with microscale courses have taught us that we must tell you that it is critical that you read, outline, and understand the manipulations you are to perform before you come to class. Processes on a small scale occur with rapidity. There is no time to study the book while reactions are taking place. You will note that every laboratory period begins with a quiz that asks questions about what you anticipate doing that day in the lab. Having read and understood the material in advance, you will find the quiz straightforward.

Chemistries 2214 and 2924 (January - April 2013)

Week beginning:



21 January

Check-in and discussion of policies, grading, safety. Begin the Diels-Alder reaction.

Begin the Diels-Alder reaction between furan and maleic anhydride. Discussion of the spectroscopy and computational tools available and their use in the laboratory and in BE220. A discussion of the use of the material on http://photon.chem.temple.edu regarding the course and the laboratory notebook.

28 January

Experiment: Check Diels-Alder reaction. Get IR and NMR spectra of maleic anhydride and furan (the starting materials).

Review Spectroscopy problems in Trinity software, use Essential Spartan on Laptops and in BE220 and WebMO to examine the Diels-Alder Reaction. Monday 4 February is the last day to drop courses without penalty.

4 February

Experiment 28: Electrophilic Aromatic Substitution (p. 368): Diels-Alder workup

Bromination of acetanilide (N-acetylaniline; N-acetylaminobenzene; N-phenylacetamide). Run IR and NMR spectra of starting materials and products. Also run IR and NMR spectra of the Diels-Alder adduct from furan and maleic anhydride.

11 February

Experiment 16: Grignard Reaction

The reaction to produce triphenylmethanol is used (p. 279). THE EQUIPMENT MUST BE OVEN DRIED . Use spectroscopic tools to identify the product.

18 February

Experiment 34: The Haloform Reaction (p. 403)

The hypochlorite oxidation of a ketone. Write a balanced equation for the haloform reaction. The actual methylketone used will NOT be the same for everyone. You must (IR, NMR) make an effort to identify your starting material and product! Experiment 34A, 34B or other methylketone may be distributed.

25 February

Special Handout: The Williamson ether synthesis

See your laboratory text p 321. Special handout Synthesis of 3-(2-methoxyphenoxy)-1,2-propanediol (guaifenesin). Use IR and NMR to identify product and check against starting materials.See http://photon.chem.temple.edu for additional information.See Stabile, R. G.; Dicks, A. P., J. Chem. Ed., 2003 ,80, 313.

4 March

Experiment 5B: Reduction of a ketone.

A metal hydride reducing agent is used for reduction of 4-tert-butylcyclohexanone to produce cis and trans-4-tert-butylcyclohexanol (p 158). Characterize the product(s) and starting materials (IR and NMR). Did your reaction go to completion? How do you know (be specific)?

11 March

Spring Holiday

Spring Holiday

18 March

Experiment 32: Hypochlorite Oxidation of an Alcohol

See page 394 of your laboratory text. Preparation of cyclohexanone by oxidation of cyclohexanol. Characterize the product(s) and starting materials (IR and NMR). Did your reaction go to completion? How do you know (be specific)?

25 March

Special Experiment Handout

Conversion of piperonal (3,4-methylenedioxybenzaldehyde) into the corresponding nitrile. Adapted from the Journal of Chemical Education.

1 April

Experiments 24A and 24B

The synthesis of N-phenylmaleimide, page 348 in your laboratory text

8 April

The Aldol condensation. Special Handout.

The reaction between 2-acetylpyridine and 4-nitrobenzaldehyde. See http://photon.chem.temple.edu for additional information and Crouch, R. D.; Richardson, A.; Howard, J. L.; Harker, R. L.; Barker, K. H. J. Chem. Ed., 2007, 84, 475. Catch-up/Make-up sign-up. Hand out laboratory practical final information

15 April


This week there is no laboratory if all laboratory assignements have been completed.

22 April

Laboratory Practical Final Examination

29 April

Check-out and written lab final quiz.

Turn in all spectra and all reports not previously handed in.

The work in this laboratory is done on your own so that, in part, it will be possible for the laboratory instructor to determine your laboratory skills.

Performance on the last quiz above minimum standards is required to pass the course.

*Technique will include items such as being careful to avoid contamination of common reagents, remembering to keep your work area clean, taking care of the equipment including re-hanging automatic delivery pipets, finishing on time, recapping reagent bottles, returning equipment to the location found, keeping only originally inventoried drawer items, etc . The ability of a student to maintain the cleanliness around balances, sorting paper waste, sharps, and broken glass and then placing these items into the proper container, as well as returning stirrer/hot plates and sand baths, will provide a measure for that student's grade.

Withdrawal: Students may withdraw from the course without penalty (Grade of "W") any time up to and through Monday, 4 February 2013. After that grace period the "W" grade is only given in accordance with institutional procedure. The procedure to obtain a "W" grade on and after 4 February 2013 is governed by the Temple University Policy (#03.12.12) on Withdrawal. Please click here to view the policy.

Incomplete: Please note that an Incomplete ("I") Grade is only given in accord with institutional procedures. The "I" grade cannot be given until specific requirements have been met and forms filled out, signed and submitted. This course is governed by the Temple University Policy (#03.12.13) on Incompletes. Please click here to view the policy.

SAFETY REQUIREMENTS: Although the Department is sensitive to the need for demonstrating personal freedom, the laboratory can be a dangerous place for its expression. Therefore, in addition to denying you admission should you refuse to wear eye protection, the Department requires:
Attendance: Simply stated, you must attend class to perform the experiments.

You will be asked to leave the class if your pre-lab preparation is insufficient, if you do not dress appropriately, lack eye-protection, or arrive late (when there is insufficient time to perform the experiment). Missing more than one quiz and failing to write up a lab may effect your grade.

Course Goals: You will be learning experimental organic chemistry at the microscale level. This means you will be working with very small amounts of materials and may become able to observe and to learn more organic chemistry in a two semesters than many previous students learned in nearly two years. Hopefully you will find this laboratory an exciting, interesting and surprisingly pleasant adventure.

The course is structured to assist you develop skills in several areas considered in lecture and the lab.