multistep synthesis - CHM 2230 Organic Chemistry II...

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CHM 2230 Experiment 8 Winter 2008 Organic Chemistry II Laboratory 3028 or 3040 Science Hall A Synthetic Competition – Multi-step Synthesis Purpose: In reality, there may be more than one way to prepare a product. The question is, which method is best? Two methods are given here to prepare methyl m -nitrobenzoate starting with acetophenone. Your purpose is to determine which is the most cost efficient path for this synthesis. Time is a valuable commodity and should be considered when making your conclusions. References : 1) Review the sections of the Carey textbook related to the three reactions performed in this multi-step synthesis. Be sure to understand the mechanistic details of the reactions. 2) This experiment is taken from Stradling, S.S.; Gage, C.L. J. Chem. Ed. 1985 , 62 , 1117-7. Please get a copy of the article (this journal must be accessed through the Science and Engineering library) and record the expected melting point of the products. This information should be included as “Product Data” in your Lab Report. Pre-lab Preparation: 1) Review the relevant sections in Carey, being sure to understand the mechanism of all reactions. 2) Your TA will assign either Path A or B to you. Read and understand the experimental procedure for your path below. 3) Calculate the molar amounts of the starting materials, intermediates, and products. You will also need to research the best purification method for each product formed if you wish to purify your product. 4) Answer the pre-lab question on blackboard prior to the start of lab. 5) Write the pre-lab section of your notebook- Date, Title, Reaction Scheme, and Table of Reagents. In the table of reagents include reagent name, MW, grams or mL amount used in experiment, molar equivalents of each reactant, and source. NOTE: All students will start with 8.0 mL of acetophenone. The experimental procedure for each reaction is similar regardless of the particular step you are on. You will need to decide if you want to purify your material at each step or wait until later in the sequence. Timeframe: Each path requires three independent reactions. You will be performing one reaction in each week of this three-week lab to complete the multi-step synthesis. Lab Report: 1) Compare the melting point of your synthesized product to melting point reported in the literature. You will need to find the expected mp by looking at the reference citing this experiment ( J. Chem. Ed. 1985 , 62 , 1117-7). What does the mp indicate to you about your product? Include the analysis of melting point in the discussion section of your lab report. 2) Calculate of the % yield of product after each of the three reactions. In addition, calculate
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multistep synthesis - CHM 2230 Organic Chemistry II...

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