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Lab IX: Nucleophilic
Substitution Reactions: Designer Experiment Submit
your Designer Lab Plan Worksheet for approval by your Instructor.
The plan
is due on or before the date given by your Instructor.
Pre-lab Questions: 1. Using ChemDraw, show the expected mechanism for the synthesis of your major product in your Designer lab. (The mechanism should show whether you believe Sn1, Sn2, E1, and/or E2 are predicted for your reaction.) Question #2 below is not directly related to your Designer Lab…but, it’s a very common type of problem related to solving unknowns, such as the products in your Designer Lab. This type of problem is known as a roadmap problem or logic problem! 2. The following information was obtained for an unknown compound: Please explain what each piece of data means and what could be a possible structure for this compound? This lab is intended to be modeled on the Competing Nucleophiles lab done earlier this semester. Each student will be doing her own individual experiment to answer her question about nucleophilic substitution or elimination reactions. Experimental Work
Experimental
Procedure
Post-lab
Questions 2. Write a short paragraph summarizing the results of your lab. Determine if your hypothesis is substantiated and explain why or why not. 3. Discuss any unexpected results and state what you would do differently if you were to do this lab again. Designer
Lab Presentation Here are the
chemicals that are available for your Designer Experiment: Alkyl Halides: bromocyclopentane, chlorocyclopentane, bromocyclohexane, chlorocyclohexane, iodocyclohexane, 1-chloroheptane, 1-bromoheptane, 1-iodoheptane, 2-bromoheptane, bromomethylcyclohexane, 1-bromo-2-ethylhexane Acids and Bases: 18M sulfuric acid, 12M hydrochloric acid, 15M phosphoric acid, glacial (100%) acetic acid, 12M potassium hydroxide, saturated sodium bicarbonate Salts and Drying Agents: ammonium chloride, ammonium bromide, ammonium iodide (Do not mix this with sulfuric acid!), potassium acetate, sodium bromide, sodium chloride, sodium iodide (Don't mix with sulfuric acid!), anhydrous magnesium sulfate, silver nitrate in ethanol, sodium ethoxide in ethanol Solvents: dimethylformide [DMF] (a polar organic aprotic solvent), tetrahydrofuran [THF] (another polar organic aprotic solvent), water, acetone, hexanes, methylene chloride, diethyl ether, ethanol, methanol **NOTE: Do not mix ammonium iodide or sodium iodide with sulfuric acid!!!** **If you wish to order a chemical NOT on the list of chemicals above,
****************************************************************************** Please model your procedure after the Competing Nucleophiles Lab. This must be a synthetic reaction!! Do not do a test tube lab as was done in the Alkyl Halide lab!! Name:
Instruments to be
used to analyze my product:
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