231L Intro to Nuc Sub Reactions TEMPLATE

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Feb 20, 2024

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NEW TEMPLATE: 231L Intro to Nucleophilic Substitution Pre-lab Questions Procedure and Safety 1. (10 pts) Write a bullet list outline for the procedure. 2. (5 pts) Write a brief summary of the key safety concerns specific for this experiment.  Choosing a Mechanism 3. This is the reaction scheme for this experiment. a. (5 pts) Label the substrate (electrophile) in the scheme above. b. (5 pts) What is the leaving group? c. (5 pts) What is the nucleophile? 4. Carbocation stability is important to examine when determining whether a nucleophilic substitution is S N 2 or S N 1. Look at the reaction scheme above. a. (4 pts) Is the substrate a 1 o , 2 o , or 3 o carbon? b. (4 pts) Does this type of carbon form a stable carbocation? 5. (10 pts) Based on what you learned from the tutorials on Canvas for today’s experiment, which substitution mechanism do you predict for the substitution reaction involving 2,5-dimethyl-2,5- hexanediol and HCl? Explain briefly why you chose this mechanism. Drawing the Mechanism Since you have chosen the type of nucleophilic substitution reaction, a mechanism for the experiment reaction can be drawn. We’ll do this step by step. 6. (25 pts) -OH is not a good leaving group. Draw the first step of the reaction between 2,5-dimethyl- 2,5-hexanediol and HCl which converts -OH into a really good leaving group. (Draw this step for one of the -OH groups.)
7. (15 pts) Now that you have a good leaving group, draw the next step for this leaving group. 8. (20 pts) Now, draw the attack of the nucleophile on the substrate (electrophile). These steps would be repeated for the remaining -OH group on the substrate to give the final product. Amounts to Use 9. (10 pts, 5 pts ea) Calculate how much substrate and reagent to use based on moles. The following table guides you in this. Substrate Reagent 2,5-dimethyl-2,5- hexanediol Conc HCl (aq) Moles 7 mmol 15x excess = 15 * 7 mmol = 105 mmol MW 146.23 g/mol NA 36.47 Concentration NA 11.65 M (or mmol/mL) Amount 1.023 9ml Data and Observations 1. (5 pts) Mass of 50 mL Erlenmeyer flask 42.224g 2. (5 pts) Mass of 50 mL Erlenmeyer flask and 2,5-dimethyl-2,5-hexanediol ___________ 3. (5 pts) Mass of 2,5-dimethyl-2,5-hexanediol 1.02g 4. (5 pts) Mass of rotovap flask 57.25___________ 5. (5 pts) Mass of product in rotovap flask ____________ 6. (5 pts) Mass of product _____________ 7. (15 pts) Insert a photo of the TLC plate showing substrate and product. The solvent front should be marked and circles drawn around any spots visualized using PMA stain. Plates should be clearly labeled with developing solvent used and what was spotted. Photo should include a ruler for calculating R f values.
8. (5 pts) Product melting point 50 c_____________ 9. (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. 10. (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. (5 pts) Calculate the R f values for the spots on the TLC plates for product. Show your work. 2. (15 pts) Calculate the percent yield. Show your work. Substrate Product 2,5-dimethyl-2,5- hexanediol 2,5-dichloro-2,5- dimethylhexane
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Mass Fill in Fill in MW 146.23 g/mol 183.12 g/mol Moles Fill in Fill in Since one mole of substrate yields one mole of product: Percent Yield = (mole product /mole reactant) x 100 3. (30 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 TLC, 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 4. Pyrazole rings are a part of the structure of a vast array of pharmaceuticals and agrochemicals. As such, reactions resulting in substituted pyrazoles are widely used in industry. The following is an example of a substitution reaction which adds complexity to the pyrazole ring.
a. (18 pts, 6 pts ea) Label the substrate, leaving group and nucleophile in the reaction scheme above. b. (10 pts) Can the substituent form a stable cation? Explain briefly. c. (14 pts) Is this reaction more likely to an S N 2 or S N 1 mechanism? Explain briefly.