City University of New York

Fall 2009

CHEM 37400/2NS: Organic Chemistry Laboratory

 

Prerequisites: Chemistry 26300 and either 26200 or 27200.

 

Meeting Place and Time: Lecture: 1109, Tue.12:30-13:20; Lab: 1109, Tue. 14:00-18:50

Instructor:          Dr. Sean S. Boson

                  Office: Marshak 1018 Phone: (212) 650-8386 E-mail: sboson@ccny.cuny.edu

 

Teaching Assistant:      Manish

                  Lab: 1205, (212) 650-6050, E-mail: msing@gc.ccny.cuny.edu

 

Laboratory Technician: Yi Pan

                  Office: Marshak 1117, (212) 650-5717, E-mail: ypan@sci.ccny.cuny.edu

 

Office hour: Mon 12:00 – 1:00 PM, 4:00 – 5:00 PM

Tue 4:30 – 5:00 PM

Thu 12:00 – 1:00 PM, 4:00 – 5:00 PM

 

Hours: 6 hr./wk; 3 cr.

 

Text:  C.F. Wilcox, M.F. Wilcox, "Experimental Organic Chemistry, A Small-Scale Approach", (2nd edition, 1995).

 

The laboratory techniques described in Chapters 1 to 15 are widely used in an organic chemistry laboratory. The physical theory of these techniques is also described in these chapters. Sections of the chapters 1 to 15, especially chapters 1 to 10, must be read carefully and frequently. Chapters 16-56 describe reactions used in preparative organic chemistry and exercises found in these chapters will be performed.

 

Course Objectives:

Organic Chemistry Laboratory II will build on the basic skills and operations of a synthetic organic chemistry laboratory and introduce advanced techniques. Stress will be placed on the identification and isolation of the products of common reaction types. To this end, we will develop the basic skill set introduced to you in Chem 262/272 and extend the set to include advanced methods for the execution of reactions, isolation and purification of crude product, identification of pure product, and purification and identification of unknown materials. You will be introduced to advanced equipment used in the Organic Laboratory to safely carrying out reactions, isolation and purification of crude product, identification of pure product, and purification and identification of unknown materials. In addition, you will perform exercises in reaction evaluation and product purification using chromatographic methods as well as spectroscopic and chemical identification methods on purified products.

 

After completing this course students should be able to:

1. Understand the fundamental principles and theory behind organic laboratory techniques commonly used for purification of compounds and separation of reaction mixtures, monitoring the course of the reactions, and analyzing reaction mixtures and products.

2. Use advanced techniques and equipment such as, flash chromatography, solid phase extraction, preparative TLC, HPLC, and GC to isolate and purify crude product and unknown materials.

3. Identify purified chemicals using spectroscopic methods (e.g. FTIR, FTNMR, GCMS, Optical Rotation, X-ray diffraction).

4. Identify purified chemicals using chemical methods (e.g. reactive indicator tests such as Tollen's silver mirror, and derivative formation).

5. Perform organic reactions in different environments (e.g. air sensitive reagents, multi-step synthesis, solid-phase synthesis, “green chemistry,” combinatorial and parallel synthesis).

6. Demonstrate proficiency in recording and evaluating experimental data including maintaining a proper laboratory notebook.

7. Write a proper laboratory report including abstract, introduction, experimental methods, results, discussion, and references.

8. Follow the safety requirements for an organic chemistry laboratory.

9. Access and utilize chemical information technology for proper experimental design and interpretation.

10. Apply ethical responsibilities and professional conduct in laboratory.

 

 

Laboratory Exercises: 4 preparative exercises and 3 technique exercises will be performed in this lab course. An exercise consists of one to many steps. It is expected that for every step a separate laboratory report is written.

 

The Laboratory Report:         You must prepare your laboratory reports in accordance with the following outline. Failure to do so will result in lost points and lower grades for the report.

 

The laboratory report is subdivided into 4 sections, labeled as shown below.

 

 

 

 

 

1.    Cover Sheet – Name, Section, Exercise Number

10

 

1

2.    Main Reaction and Mechanisms Physical Properties, all materials; Limiting Reagent; Theoretical Yield; Side Reactions and Mechanisms.

25

 

2

3.    Separation Scheme, flow chart

45

 

3

Procedure and lab. skills

 

 

4

4.    Actual and Percentage Yields

_ 20

 

 

 

100

 

                                                                            

 

Sections 1, 2 and an outline of 3 must be prepared at home, during the week preceding the first laboratory session for the new experiment. This preliminary laboratory report must be ready at the beginning of the lecture of the laboratory session for that experiment. The outline of section 3 should be transcribed into your laboratory notebook.

 

Section 3 and 4 must be completed in the laboratory. The completed laboratory report must be handed in on the last day assigned for the particular experiment. Failure to do so will result in a 10 point penalty for the report grade.

 

The sections of the report are discussed in the textbook on pages 10 to 18, and pages 531 to 534 (Appendix D). Note that we require a slightly different sequence for the presentation of the sections than is described in the textbook; however, the textbook will provide valuable information and samples for you to follow in the proper preparation of the laboratory report.

 

The preliminary laboratory reports (sections 1 and 2 can be hand written or prepared on a word processor). The final sections 3 and 4 will be hand written since they will be prepared in the laboratory.                                 

 

The Laboratory Examinations: The laboratory examinations will test your knowledge of the theoretical basis of the exercises that are performed and will be conducted to evaluate your preparedness for the experiments. They will be drawn from all of the recommended reading, the theory of the experiments performed, and the techniques applied.

 

The chapters which describe techniques especially relevant to each exercise are listed on the schedule with the exercise numbers. You are strongly advised to read the chapters in the textbook. Some techniques will be used more than once in the laboratory course, the examination questions on techniques will be chosen based only on the relevance of the techniques to the particular laboratory exercise.

 

Make-up Sessions, Absences: No make-up exams, or laboratory sessions, will be arranged. It is your responsibility to ensure that you attend all the laboratory sessions, on time. An absence from a laboratory without a suitable strong excuse will result in a mark of zero being assigned.

 

Final Examination:       There will be no written final examination for Chem37400.

 

Grading: The laboratory reports (best 6 out of the 7 exercises) will account for 50% of the final grade, the examinations during the semester (best 6 of 7 exams) will provide 20%,and individual performance in the lab accounts for 30%.

 

 

Safety:  All of the safety regulations that are outlined in chapter 1 must be adhered to. (Safety goggles will be worn at all times. Neither contact lenses, nor open-toe shoes are allowed in the lab). Any willful violation of our safety rules will result in the student’s immediate expulsion from the laboratory and the award of a laboratory grade of F.

 

Breakages: You will be charged the replacement cost of any equipment which you break during the lab course. Some of our glassware is especially expensive and so you are urged to work carefully at all times.

 

 

 

 

Section 2NS: Lecture: 1109: Tue.12:30-13:20; Lab: 1109: Tue. 14:00-18:50

SCHEDULE OF EXPERIMENTS

 

Week 1 Sept. 1

Introduction, Check In, Chemical Literature Research

-

Week 2 Sept. 8

Recrystallization, TLC, Melting Points, Boiling Points Measurement, FT-IR/ATR Training

Handout

Week 3 Sept. 15

Natural Products—Separation of Cinnamaldehyde from Cinnamon via Steam Distillation and Soxhlet as well as Synthesis of Cinnamaldehyde [Steam Distillation, Soxhlet Extraction, IR, GC/GC-MS (if available), and TLC]

Part I: Steam distillation

Handout

Week 4 Sept. 22

Natural Products—Separation of Cinnamaldehyde from Cinnamon via Steam Distillation and Soxhlet and Synthesis of Cinnamaldehyde [Steam Distillation, Soxhlet Extraction, IR, GC/GC-MS (if available), and TLC]

Part II: Soxhlet Extraction

-

Week 5 Sept. 29

No Class (Monday Schedule)

-

Week 6 Oct. 6

Natural Products—Separation of Cinnamaldehyde from Cinnamon via Steam Distillation and Soxhlet and Synthesis of Cinnamaldehyde [Steam Distillation, Soxhlet Extraction, IR, GC/GC-MS (if available), and TLC]

Part III: Synthesis, IR, and GC-MS Analysis

-

Week 7 Oct. 13

Isolation of [R]-[-]- and [S]-[+]-Carvone from Spearmint Oil and Caraway Seed Oil (LC Chromatography, Vacuum Distillation, GC/GC-MS, TLC, and IR Spectroscopy)

Part I: Vacuum Distillation

 

Handout

Week 8 Oct. 20

Isolation of [R]-[-]- and [S]-[+]-Carvone from Spearmint Oil and Caraway Seed Oil (LC Chromatography, Vacuum Distillation, GC/GC-MS, TLC, and IR Spectroscopy)

Part II: Liquid Column Chromatography

-

Week 9 Oct. 27

Isolation of [R]-[-]- and [S]-[+]-Carvone from Spearmint Oil and Caraway Seed Oil (LC Chromatography, Vacuum Distillation, GC/GC-MS, TLC, and IR Spectroscopy)

Part III: GC/GC-MS, IR and TLC Analysis

-

Week 10 Nov. 3

Single Unknown Isolation and Identification I (Using Solubility Test, Functional Group Test, Elemental Analysis, TLC, IR, Melting Points and Boiling Points, and Derivatives Methods)

Handout

Week 11 Nov. 10

Single Unknown Isolation and Identification II (Using Solubility Test, Functional Group Test, Elemental Analysis, TLC, IR, Melting Points and Boiling Points, and Derivatives Methods)

-

Week 12 Nov. 17

Unknown Mixture Isolation and Identification I (Using Solubility Test, Functional Group Test, Elemental Analysis, TLC, IR, Melting Points and Boiling Points, GC-MS, and NMR Methods)

Handout

Week 13 Nov. 24

Unknown Mixture Isolation and Identification II (Using Solubility Test, Functional Group Test, Elemental Analysis, TLC, IR, Melting Points and Boiling Points, GC-MS, and NMR Methods)

-

Week 14 Dec. 1

Unknown Mixture Isolation and Identification III (Using Solubility Test, Functional Group Test, Elemental Analysis, TLC, IR, Melting Points and Boiling Points, GC-MS, and NMR Methods)

-

Week 15 Dec. 8

Check Out