Organic Chemistry Lab 7

Organic Chemistry Lab 7 - November 7th, 2007 Craig Nutter...

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November 7 th , 2007 Craig Nutter Section #9, Wed. 2:30 Experiment 7 Title: Stereochemistry of Bromine Addition to Cinnamic Acid Objective: To understand the stereochemistry of Bromine addition to Cinnamic acid, and identify the stereo-chemical structure of the unknown dibromide product using the product’s melting point and mass. Reaction: Reagent Table: Substance Amount Added Transcinnamic Acid 83 mg Pyridinium Tribromide 200 mg Glacial Acetic Acid 1 mL
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Question from handout: If there is a broad range, then both diastereomers are present. If there is a mixture of enantiomers, then there will be no chance in the melting point because enantiomers have the same physical properties. This would result in a narrow melting point range. Procedure and Observations: Procedure 1. 83 mg of trans-cinnamic acid and 200 mg of pyridinium tribromide were added to a 5 mL conical vial. 2. 1 mL of glacial acetic acid was then added to the vial. 3. An air condenser was then attached to a vial, and a magnet spin vane was inserted into the vial. 4. The vial was then clamped to a red pie block. 5. The hot plate was set to 5, allowing the device to heat at 105°C. 6. The solution was heated for 25 minutes. 7. The vial was then removed from the pie block after being heated for 25 minutes. 8. The air condenser and spin vane were then removed from the vial. 9. 1 mL of water was added to the reaction vial and stirred with a spatula. Observations Magnet vane began to spin. The solution became yellow-orange in color. Solution began to crystallize.
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10. After being cooled to room temperature, the reaction vial was placed into an ice bath for 10 minutes. 11. During this time period, a
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This note was uploaded on 04/07/2008 for the course MCMP 204 taught by Professor Berkstrom during the Spring '08 term at Purdue University.

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Organic Chemistry Lab 7 - November 7th, 2007 Craig Nutter...

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