PRE_LAB_8

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University of Houston *

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Chemistry

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Feb 20, 2024

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I. Brominating Alkenes October 21, 2023 II. Answers to Pre-Laboratory Questions: 1. What safety precautions must be observed when using: a. Pyridinium Tribromide? When using pyridinium tribromide you must avoid inhaling, eye contact, skin contact, and ingesting this reagent, use a fume hood to dispense this reagent. b. Acetic acid? When using acetic acid you must avoid inhaling, eye contact, skin contact, and ingesting this reagent, use a fume hood to dispense this reagent. 2. Calculate the theoretical yield for the bromination of both stilbenes, assuming the presence of excess pyridinium tribromide. Note the theoretical yields here and in your laboratory notebook. For the theoretical yield of both stilbenes the molecular weight of 1,2-dibromo-1,2- diphenolethane must be used, as well as the moles of both stilbenes. Molesof cis stilbene = 0.1 mL× 1.01 g mol 180.25 g mol = 0.00056 moles Molesof trans stilbene = 0.1 g 180.25 g mol = 0.00055 moles The theoretical yield can now be calculated: Theoretical yield of cis stilbene :0.00056 mol× 340.05 g mol = 0.1907 g Theoretical yield of trans stilbene = 0.00055 mol× 340.05 g mol = 0.1887 g 3. Draw the mechanism, including the intermediate bromonium ion, generated in the bromination of trans-2-butene.
4. a. Look up and draw structures for cis-stilbene and trans-stilbene. b. Predict the relative stereochemistry of each product and draw the predicted structures. III. Purpose: The purpose of this experiment is to create vicinal dihalides by brominating alkenes. By doing this experiment I hope to learn how to identify and test the stereo of these vicinal dihalides.
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