Project #62062 - Organic chemistry pre-lab

Example attatched (doesn't include the needed HNMR table). Lab procedure at the bottom.

You need the following, in this order:

  1. Title of experiment
  2. The reaction scheme for the specific reaction you are performing. No mechanism is included in the scheme. Underneath the structure of reactants write how much you are using, g or mg for solids, mL and density for liquids, also how many mmol of each you are using. Get this information from the procedure or online resources. Indicate in your scheme which reactant is limiting. Indicate in your scheme which product is the desired product and the theoretical yield in mmol and either g or mg.  Add above or below the arrow any solvents and conditions for the reaction. All the reactants should be to the left of the reaction arrow.
  3. Prepare a table of reactants and products and their pertinent information. Column headings are name, structure, MF, MW (g/mol), density (if a solid the say NA), amount used for reactants (g or mg for solids, mL for liquids), mmol used, mmol expected for products, theoretical yield for products g or mg and hazards. Each reactant and organic product is a row in the table.
  4. Prepare a table of reaction solvents and workup solutions. The columns for this table should be name, structure, bp, density, purpose (be specific i.e. “removes H2O”, “removes ions”, “neutralizes” etc.) and hazards. All of the information for 3 and 4 can be found in the procedure or online. Sigma-Aldrich Catalog is a good source. Chemfinder is another option.
  5. Obtain reference IR spectra for starting material and expected product. SDBS is a good source. You can also search online using the name along with the type of spectrum you are looking for. Organize IR data of the product(s) into table(s). For the IR table, the two column headings are structure and IR Diagnostic Bands (cm-1). The correct format for listing data in the second column is stretch, frequency range, descriptors. For example a broad,  medium sp3C-H stretch from 2800 -3000 cm-1would be: sp3C-H, 2800-3000, b, m.  You will be doing a full analysis of all non-fingerprint region bands of any acquired spectra.
  6. Obtain proton NMR spectra for the starting material and expected product. Organize the NMR information for the expected product into a table. You will need the structure of the product with the non equivalent H's labelled alphabetically. For each H set you will need chemical shift, multiplicity, J values if applicable and how many H are generating the signal. Each
  7. Draw out a formal curved arrow electron pushing mechanism for the reaction you are performing in the laboratory. You will need to show intermediates but not transition states.
  8. You can use chemical drawing software or copy and paste from a reference. If you have a reference be sure and cite it.  Save the entire pre lab as one document. Also save as a pdf file and upload the pdf file.


 Lab 8 Iodination of Anisole

Formation of the Electrophile.

The electrophile is formed when potassium iodide (KI) and potassium iodate (KIO3) is treated with a mineral acid (H+). This starts a cascade of reactions that we will not go into detail about. The net result is the formation of I+ which functions as the electrophile. Notice the iodine containing reagents are less moles than anisole. We are not showing the balanced reactions that produce I+. 3 moles of IO3 and 2 moles of KI are required per mole of anisole. The elctrophile has to be produced in excess.

Reaction Procedure

1. In a 250 mL round bottom flask equipped with a stir bar, Claisen head with reflux condenser and addition funnel combine 1.0 g (9.26 mmol) of anisole, 1.03 g (6.22 mmol) of potassium iodide, 0.66 g (3.08 mmol) of potassium iodate, 5 mL of methanol, and 30 mL of water. 

2. Add 9.5 mL (9.5 mmol) of 1 M HCl to the addition funnel Add acid to the reaction mixture over 40-45 minutes (a rate of about one drop per 13 seconds). 

3. Ideally, the solution should stir at room temperature for an additional 2-3 hours. Allow the solution to continue stirring until 45 minutes of lab time remains then proceed to the workup phase. 


1. Add 50 mL of water to the mixture and transfer it to a clean separatory funnel. 

2. Extract the organic layer with 25 mL dichloromethane three times. 

3. Combine the organic layers, wash the organic layer with with 25 mL of 5 % aqueous sodium thiosulfate. This removes any iodine formed during the reaction. This is a reaction so be to sure to shake well. If the organic solution remains colored repeat.

4. Wash the organic layer with 25 mL of water, and then with 25 mL of brine.

4. Dry the organic layer with MgSO4, filter to remove drying agent into a tared round bottom flask.

5. Remove the solvent via rotary evaporation.

6. The resultant crude product is an oil. Determine the % yield. Obtain an IR spectrum and prepare a proton NMR sample.

Subject Science
Due By (Pacific Time) 03/14/2015 05:00 pm
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