Write a mechanism for the Diels-Alder reaction of anthracene and maleic anhydride

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Write a mechanism for the Diels-Alder reaction of anthracene and maleic anhydride. Be ascomplete as possible and show electron flow for all steps.CHEM 2204 SP 2016Lab Report Instructions for Expt 15: Diels-Alder Reaction: 9,10Dihydroanthracene-9,10-α,β-succinic Acid AnhydrideGeneral Information• Your report MUST be typed and should NOT be submitted on laboratory notebook pages.Much of the information and data from your lab notebook will be transferred to your report, butyou will not submit any lab notebook pages with or as part of your report. Copies of your labnotebook pages should have been submitted when you left lab on the day of the experiment.• The lab report is due at the beginning of the lab period on the week following the completionof the experiment. For this experiment, the due dates will be during the week of January 26.Specific Information for Experiment 15Your report will consist of the following sections. Use the headers listed below to designate eachsection, except for the Title.Title: The title of the experiment, the experiment number, and the date that the experiment wasperformed in lab. This information is identical to that required in your pre-lab write-up. The titleshould be complete and accurate. The following example is given to help set expectations andmay be used directly in your report:Experiment 15: The Diels-Alder Reaction: 9,10-Dihydroanthracene-9,10-α,β-succinic AcidAnhydrideObjective: List the goals, or the purpose, of the experiment. This information is identical to thatrequired in your pre-lab write-up.Experimental Procedure: You do NOT need to copy the experimental details that wereincluded in your pre-lab write-up. It is sufficient to include a reference to the source of theprocedure, as well as any modifications that were posted on Blackboard. If necessary, thesestatements should be followed by a list of any additional modifications to theexperimental procedure (list in bulleted, complete sentences). It is very important that youdocument any changes to the procedure in your lab notebook at the time of the experiment, andinclude them in your report. This section may help to explain unexpected results, for instance.The following example is given to help set expectations and may be used directly in your report:The procedure was followed as described in Mayo, pages 271-272, with the modifications listedin the Blackboard document. Additional modifications to the procedure included the following:(list in bulleted, complete sentences)• (if necessary)Reaction Scheme: A balanced chemical reaction consistent with the experiment beingconducted, including reactants, products, solvent(s), and reaction temperature. This scheme isidentical to that required in your pre-lab write-up and should immediately precede the Data andResults Table (see below). The reaction scheme may be hand-written, but please be as neatand clear as possible.Lab Report: Diels-Alder Reactionpage 2Using any form of electronic copy and paste to reproduce directly a reaction schemefrom any source, including the printed or electronic lab textbook, is a violation of theAcademic Integrity policies of this course. All parts of your lab report – text, schemes,tables, etc. – must be in your own words. You may draw the reaction scheme by hand(preferred), or use some type of drawing program, but it must be your own work.The following example is given to help set expectations and may be used directly in your report):OO+Oxylenesre?uxHHOOOData and Results: Organized in three parts as shown below.Data and Results TableGive original data and calculated values in an organized tabular format, essentially, an updatedversion of the Reaction Table from your pre-lab.• Include appropriate units and pay attention to significant figures.• Data may differ slightly from that reported in your pre-lab write-up. You must report and usethe actual values in your calculations. In this way, your final results and conclusions matchwhat you actually did in the experiment, not what you intended to do in your pre-lab.• The product amounts in the table (g or mg and mmol) must include the calculatedtheoretical yield (TY) based on the reaction stoichiometry. The experimental yield (EY) mayalso be listed in the Table and must be reported in the Calculations section of the report (seebelow).As with the Reaction Scheme, using any form of electronic copy and paste to reproducedirectly a data table from any source, including the printed or electronic lab textbook, isa violation of the Academic Integrity policies of this course. You are responsible forcreating your own table (either written by hand, or using Word or Excel).Below is a sample Data and Results Table for this lab, and in this case, you may use it as atemplate in your report. YOUR experimental amounts should be reported, which are notlikely to be the same as the sample amounts below:anthracenemol. formulaamount (mg)amount (mL)mmolesmolar massdensitylit. bp (°C)lit. mp (ºC)maleic anhydrideC14H1080xylenesC 4H 2O 3409,10-dihydroanthracene-9,10α,β-succinic acid anhydrideC18H12O3110 (TY)77 (EY)1.00.45178.230.4198.060.41 (TY)0.28 (EY)276.300.86137-140261-262Lab Report: Diels-Alder Reactionpage 3ObservationsData includes all relevant observations, such as heat evolved, initial color and color changes,precipitate formation, state of product, product melting point range, etc. Observations shouldbe listed in bulleted, complete sentences.CalculationsFor all calculated values in Chem 2204, show ALL work. This part does not have to betyped, and you may prefer to leave space in your document and enter the calculations by hand.Please be as neat as possible.Note the distinction between yield and % yield. A yield is simply an amount of product (howmuch was formed?) and is also referred to as an actual or experimental yield. For example, theyield of the reaction was 152 mg of product. A % yield relates how much of a product isproduced (actual or experimental yield) compared to the theoretical maximum that could havebeen formed (theoretical yield). See pages 42-43 in the lab textbook.The theoretical yield calculation in the lab report should always begin with the amountmeasured or weighed in lab of the limiting reactant. Be sure to use the actual amounts ofeach reactant that you used, and not the intended amount. For solid reactants, the amountactually measured at the balance may differ by a few mg from the target amount. This actualamount must appear in your lab notebook and lab report data table (above) and must be used inthe theoretical yield calculation, if appropriate (for instance, if the solid reactant in question is thelimiting reactant).Show ALL work! Write or type all three calculations and include all units:1) Theoretical yield of 9,10-dihydroanthracene-9,10-α,β-succinic acid anhydride.2) Yield of 9,10-dihydroanthracene-9,10-α,β-succinic acid anhydride3) % Yield of 9,10-dihydroanthracene-9,10-α,β-succinic acid anhydrideQuestions: Answer the following questions. Be as complete as possible, and always explainyour reasoning.1. Write a mechanism for the Diels-Alder reaction of anthracene and maleic anhydride. Be ascomplete as possible and show electron flow for all steps.*Note: Do NOT simply write out the book mechanism without any critical review. It may not becomplete in terms of showing ALL electron flow (proton transfers, in particular, are oftenassumed and not drawn out fully). You are responsible for writing complete reactionmechanisms that are inspired by the rules and guidelines set forth in both the lab AND lecturecourses.2. The internal reaction temperature (in other words, the temperature of the reaction mixtureinside the reaction flask) of this Diels-Alder experiment may be specified by the term reflux.a) What was the internal reaction temperature, in °C?b) How was the internal reaction temperature achieved and maintained?Lab Report: Diels-Alder Reactionpage 42. Diels-Alder reaction rates…a) Which of the following dienes will react faster in a Diels-Alder reaction, cyclopentadiene or1,3-butadiene?cyclopentadiene1,3-butadieneb) Explain your answer. Be as complete as possible and include any necessary chemicalstructure(s).3. Predict the structure of the product formed in the following reaction.O?O+OO4. For each of the following products, draw the structures of the diene and dienophile necessaryto synthesize the compound in a Diels-Alder reaction.OOa)b)OOc)OOOWorks Cited: Full references for the experimental procedure(s) in the appropriate format.Include references for any relevant physical properties that were not included in the labtextbook.1. Mayo, D. W.; Pike, R. M.; Forbes, D. C. Microscale Organic Laboratory with Multistep andMultiscale Syntheses, 5th ed.; John Wiley & Sons, Inc., 2011; pp 269-273.2. Modifications for Expt 15: Diels-Alder Reaction: 9,10-Dihydroanthracene-9,10-α,β-succinicAcid Anhydride, Blackboard document.