231L Alkene Addition TEMPLATE

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Iowa State University *

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Chemistry

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Feb 20, 2024

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NEW TEMPLATE: 231L Alkene Addition Pre-lab Questions Procedure 1. (10 pts) Write a bullet list outline for the procedure. Setup reflux 2. (5 pts) Write a brief summary of the key safety concerns specific for this experiment. Mechanism 3. (25 pts) The first step in the bromination of an alkene is the nucleophilic attack of the alkene on the bromine. This attack causes the loss of the bromide ion leaving group. A bridged bromonium ion is formed. This is shown below with cyclpentene. Draw the first step in the mechanism for today’s reaction between trans -cinnamic acid and bromine. 4. The next step for bromination of an alkene is nucleophilic attack of bromide on the bromonium ion. The bromide attacks one corner of the bridge as shown below. a. (4 pts) Given that syn addition would give both bromines on the same side and anti addition would give bromines on opposite sides, what type of addition is halogenation of alkenes? b. (20 pts) Draw this step for the bromination of cinnamic acid. 5. (8 pts) Another aspect of bromination that must be considered is stereochemistry. For the bromination of trans-2- butenoic acid, two chiral centers are formed in the product (indicated by stars).
Due to the presence of chiral centers, four different stereoisomers are possible: (Solid wedge mean bond is coming out of paper towards you. Dashed wedge means bond is going out the back of the paper.) However, only two products are observed. Which two of the above products would be consistent with the addition mechanism of bromination of alkenes? Circle these products above. 6. (13 pts) Draw the product for the bromination of trans -cinnamic acid (do not use wedges and dashes, yet) and put a star by each chiral carbon. 7. (32 pts) Draw the four possible stereoisomers for the bromination of trans -cinnamic acid using wedges and dashes. 8. (8 pts) Which two of the stereoisomers you drew would be consistent with the addition mechanism of bromination of alkenes? Circle the products you would expect in the bond line structures you drew above.
9. (25 pts) Draw a reaction scheme today’s reaction. Include stereochemistry and all possible products consistent with mechanism. Amount to Use 10. (5 pts) Calculate how much cinnamic acid to use based on moles. The following table guides you in this. Reactant trans- cinnamic acid Moles 0.01 mol MW 148.16 g/mol Amount Fill in Data and Observations 1. (5 pts) Mass of roundbottom flask. 22.337g 2. (5 pts) Mass of cinnamic acid and flask________ 3. (5 pts) Mass of cinnamic acid. 1.484g 4. (5 pts) Mass of watch glass 27.31g 5. (5 pts) Mass of product on watch glass 29.49 g 6. (5 pts) Mass of product _____________ 7. (5 pts) Product melting point 268C – 275C 8. (20 pts) Insert a photo of your FTIR spectrum for your product. Draw the structure of your product on or near the spectrum. Label the peaks in the spectrum which correspond to functional groups in your product. The FTIR spectrum of cinnamic acid is provided below for comparison.
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9. (20 pts) As you are performing the synthesis, record any issues you had or what you could have done differently in order to get better results. Analysis and Application Questions Analysis 1. (15 pts) Calculate the percent yield. Show your work. Reactant Product Cinnamic acid 2,3-dibromo-3- phenylpropanoic acid Mass Fill in Fill in MW 148.16 g/mol 307.97 g/mol Moles Fill in Fill in FTIR Cinnamic Acid
Since one mole of substrate yields one mole of product: Percent Yield = (mole product /mole reactant) x 100 2. (20 pts, 10 pts for specifically explaining how each type of data supports claim) Was your synthesis of 2,5-dichloro-2,5-dimethylhexane successful? Explain. Use your FTIR, and melting point data as evidence in your explanation. Remember that you need to be specific when using data as evidence of your claim of success or lack of success. If you were unsuccessful, use the issues you recorded while doing the experiment to make a specific suggestion for what you would do differently to get better results. Application 3. (25 pts) Complete each reaction. Show the stereochemistry of each product. 4. A variety of different species can be added across an alkene double bond which makes alkenes incredible useful in industry. For example, ethene derived from petroleum is used to produce PVC. One industrially important synthesis is the addition of hydrogen, H 2 , across alkene double bonds. This is accomplished using hydrogen gas and a catalyst such as nickle. Let’s look at this reaction using the starting material used in this experiment, cinnamic acid:
a. (5 pts) Unlike Bromine, hydrogen is added across the double bond in a syn fashion. The above product is drawn without showing stereochemistry. Redraw the product showing a syn addition of hydrogens by using wedges and dashes. b. (5 pts) Considering stereochemistry, how many products will result from this reaction? Hint: Does the product have the same chiral carbons as the bromination product?
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