Synthesis and Characterization Laboratory 448

Spring 2009
 
 Tuesday January 20th CHECK IN (all students) and instrumentation instruction.

General Information
 

Instructors

Organic Section - H. Thompson, Olson 320, Ext. 5520. Inorganic Section - F. Jaekle, Olson 336, Ext. 5064

 

 

Teaching Assistants

Organic Section – Puilam Chiu, Olson 229. Inorganic Section – Cheng Fei, LSC 3rd floor

 

 

Lecture

Wed., 1:00 - 2:20 PM, Smith Hall-240

Laboratory

Tues.  1:00 - 5:15 PM, Fri. 1:00 - 5:15 PM LSC

 

 

 

You will work in groups of two for each of 7 experiments; 3 Organic and 4 Inorganic/Materials.
Following the guidelines given below, you will independently submit a report for each experiment.

Text

Individual handouts for each experiment

Exam and Grading

There will be a final exam covering material from the laboratory experiments and lectures.
Overall course grade will be determined according to the following scheme.

 

Laboratory Reports A-F; 6 x 11% = 66%
Laboratory Report G; 7%
Final Exam: 27 %

 

 


 

Each student does the following 7 multi-part experiments on a staggered and rotating schedule so that no experiment is simultaneously done by more than 3 students. (See schedule)
NO STUDENT WILL BE ALLOWED TO START THE LABORATORY
UNTIL THEY HAVE PAID FOR THE FEE CARD IN THE STOCKROOM.
NO EXCEPTIONS!

 

Organic

A. Epoxidation of an a,b-unsaturated ketone. Tosylhydrazone cleavage of an a,b-epoxy ketone. Oxidative KMnO4 cleavage of an alkyne.

B. Catalytic hydrogenation of an unsaturated acid anhydride. Friedel-Crafts acylation of benzene with an acid anhydride. Stereochemical equilibration of a cyclohexyl ketone. Catalytic hydrogenolysis of a benzoyl group. Acid-catalyzed cyclization of a g-phenyl carboxylic acid.

C. Enamine alkylation of cyclohexanone. Alkylation of a dienamine. Saponification of a keto ester

 

Inorganic/Materials

D. Transition-metal-catalyzed polymerization reactions. Ring-opening metathesis polymerization and atom tramsfer free radical polymerization.

E. Organometallic chemistry. Reactions of bis(cyclopentadienyl)iron(II), ferrocene.

F. Organometallic polymer chemistry. Synthesis of a ferrocene-based polymer via ring-opening polymerization.

G. Siloxane chemistry. Preparation of "bouncing putty", a silicone polymer with unusual properties / or X-ray Crystallography

 

 


 

General Guidelines for Performing Experiments

Be prepared! Before each session you must read the experimental procedure in advance. This will allow you to manage your time better and have everything prepared in advance for each step of the procedure. Delays caused by having to go to the stockroom frequently, or to clean glassware may prevent you from finishing the lab. Also, if the material is sensitive, delays can cause the experiment to fail due to decomposition.

DO NOT RUSH! A good synthetic chemist gets the experiment done in time, in good yield and with a minimum of impurities. However, having to rush may cause the experiment to fail or produce impure products. For example, if a sample is not fully dried this will show up in the spectral data. If you manage your time well, there is ample time to finish without rushing.

Wash glassware carefully and dry it (in an oven for the inorganic experiments) before use and when you have finished. Do not leave dirty apparatus for the next group!!

Dispose of all wastes in the appropriate containers. Do not flush anything down the sink that is toxic!!

Protective eye-wear must be worn at all times in the lab. Latex or vinyl gloves should be worn when transferring or weighing chemicals or solvents, then disposed of.

AT THE END OF EACH 2 WEEK SESSION, RETURN THE GLASSWARE FOR EACH LAB BACK TO THE STOCKROOM OR TO THE STOCK CABINETS IN 001 AND 007 AS APPROPRIATE. THERE IS A LIMITED NUMBER OF SOME EQUIPMENT ITEMS, DO NOT SEQUESTER IT.

 


 

Guidelines for Submitting Laboratory Reports to Dr. Jaekle. (D-G) 
(Note: Reports submitted to Dr. Thompson should follow the guidelines given at the beginning of the lab procedures for Expts A-C.)

The outline of your report should follow the headings on the next page. Please assemble all vertical-format pages right side up and all horizontal-format pages with top at left. Staple or clip the report at the top left.

You are responsible for recording your own data and for writing and submitting your own laboratory report.

Spectra (NMR, IR, GCMS) should be obtained and interpreted. Make all spectral assignments and annotations that point out important aspects of the data directly on the spectra and DO NOT write separate text for this except in extraordinary cases. 


Typewritten reports are required.

For your lab reports drawings of the relevant reactions schemes are required. For this purpose you may use either  Chemdraw or Chemsketch. Rutgers currently has a site license for ChemDraw. Anyone with a Rutgers email address can download the software.
First login at the Rutgers software portal, search for ChemDraw, and click on the "Cambridgesoft" link. Students must then register with ChemDraw to obtain the software. Note that the site does not recognize email addresses with the newark.rutgers.edu alias -- use yourname@pegasus.rutgers.edu, or just yourname@rutgers.edu. Chemsketch is a free software package, which can be downloaded at http://www.acdlabs.com/download/

Neat and well-organized write-ups are more likely to receive high grades.

Pay careful attention to formulas. Write them properly; for example, [Bu4N][PF6] is the salt called tetrabutylammonium hexafluorophosphate; the [ ] denote complex ions. Also, if you name a compound, use the IUPAC nomenclature from your Organic or Inorganic Textbooks

Reports must be handed in 2 weeks after completion of the experiment (see schedule). For every 2 days late you will receive 90% of the grade you would have gotten if it were handed in on time. For example, an A turns into a B after two days and into a C the fourth day, and into a D six days after its due date, etc.


 


 

Report Outline

1. Introduction

A very brief summary of the experiment including a reaction scheme (use a drawing program!).

2. Experimental Section - Lab Notebook pages (submit copies of the original lab notebook pages, do not rewrite them)

An extremely important aspect of any lab is to make careful observations. Weights, melting points, color changes, evolution of gases and changes in temperature are examples of observations that may indicate something important is occurring. Make detailed notes in your lab notebook as you perform the experiments. Copies of these notes must be submitted in this section of your write-up and should include weights, observations, details of the procedure followed, etc.

Do not write out the procedures in detail; we know them well and do not want to read through them again.

3. Results 

Record all mass yields, calculate percent yields of the products, and show your calculations, based on the correct molecular weights of reactants and products and accounting for counterions and solvents molecules of crystallization if necessary. Also show the molecular weight calculations for the polymers using all data available.

4. Discussion 

Explain the spectral data of your products with notations on the spectra and use this to prove that you have the correct compounds. If the spectra are poor and contain impurities explain what the impurities are and why they are present. For example, NMR and IR spectra will indicate the purity of your product and whether it is wet, and a mass spectrum may have many peaks due to different isotopes of some of the elements in the compounds. The MS may also show some impurities that have to be pointed out. Similarly, GPC data may show low molecular weight impurities in your polymers. Also compare your experimental MW data (GPC, NMR) with theoretical molecular weights as appropriate.

 

You must account for all these observations in this section of your report. In addition, you should discuss important experimental observations in the context of the chemistry involved. Relevant information is given in the lectures and by the Professor and TA's during the lab sessions, listen carefully during the labs. Additional information should be obtained from relevant texts and compilations in the library and through the internet.

The goal of your report is to explain YOUR observed experimental data in the context of the expected results. Reports that merely explain what the data should be and not the observed results will receive low grades.

5. Spectra

Attach all of your spectral data with your notations to the end of your report. Put your spectra in experimental order and within that: GC/MS, then IR, then 1H NMR, followed by 13C NMR. For the organic experiments, pay attention to the authentic spectra in the handouts, which are of materials of high purity.  Learn how to recognize common impurities that may show up in your spectra, particularly solvents (including spectral solvents).

 

Synthesis and Characterization Spring 2006

Schedule for conducting experiments and submitting reports.*
 

Session

1

2

3

4

5

6

7

 

Date Lab Performed

1/23-2/3

2/6-2/17

2/20-3/3

3/6-3/24

3/27-4/7

4/10-4/21

 4/24-4/28

5/1

Due Date

2/18

3/4

3/25

4/9

4/22

5/1

 5/8

M

Exp. A

1&11,2,12

3

4,5

9

7,10

8,6

 

A

Exp. B

3,4

5&11,8

12

1,6

2,9

7,10

 

K

Exp. C

5,6

2,4

1,10&11

7,12

8

3,9

 

E

Exp. D

7,8&11

1,12

3,9

4,10

6 

2,5

 

U

Exp. E

9,10

6&11,7

2,8

3,5

1,4&12

 

 

P

Exp. F

 

9,10

6,7&11

2,8

3,5

1,4&12

 

 

Exp. G

 

 

 

 

 

 

To be determined

 

* NOTE: Experiment F (5 lab sessions) must be started during the last session of Expt E (3 lab sessions).

 

updated 01/13/2009  FJ