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When ethyl acetoacetate
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Organic Chemistry
- Ethylene oxide is the starting material for the synthesis of 1,4-dioxane. Propose a mechanism for each step in this synthesis.arrow_forwardOne frequently used method for preparing methyl esters is by reaction of carboxylic acids with diazomethane, CH2N2. The reaction occurs in two steps: (l) protonation of diazomethane by the carboxylic acid to yield methyldiazonium ion, CH3N2+, plus a carboxylate ion; and (2) reaction of the carboxylate ion with CH3N2+. (a) Draw two resonance structures of diazomethane, and account for step 1. (b) What kind of reaction occurs in step 2?arrow_forwardAccount for the fact that treating propenoic acid (acrylic acid) with HCl gives only 3-chloropropanoic acid.arrow_forward
- When 2-pentene is treated with Cl2 in methanol, three products are formed. Account for the formation of each product (you need not explain their relative percentages).arrow_forwardIdentify the best reagents to complete the following reaction.arrow_forwardH3C. H3C. CH3 nnc» XT :OH 2 CH₂OH HCI catalyst Aldehydes and ketones react reversibly with two equivalents of alcohol in the presence of an acid catalyst to give acetals. Alcohols are poor nucleophiles, and so protonation of the carbonyl oxygen is used to make the carbonyl carbon a stronger electrophile. Addition of the first equivalent of alcohol gives a hemiacetal, a hydroxyether. Addition of the second equivalent of alcohol is accompanied by loss of water to yield the product acetal. Draw curved arrows to show the movement of electrons in this step of the mechanism. Arrow-pushing Instructions CH3 H3C CH3OH H3CQ OCH3 CH3 H3C. H HO: :OCH 3 CH3 46arrow_forward
- Draw the products formed when CH3CH2C=C Na+ reacts with following compound. propene oxide followed by H2Oarrow_forwardWrite the reagents used to synthesise the following compound starting from the benzoic acidarrow_forwardProstaglandins are a class of eicosanoids, fatty acid derivatives with a variety of extremely potent actions on vertebrate tissues. They are responsible for producing fever and inflammation and its associated pain. Prostaglandins are derived from the 20- carbon fatty acid arachidonic acid in a reaction catalyzed by the enzyme prostaglandin endoperoxide synthase. This enzyme, a cyclooxygenase, uses oxygen to convert arachidonic acid to PGG2, the immediate precursor of many different prostaglandins. Rate of formation of PGG2 with 10 mg/ml ibuprofen (mM/min) Arachidonic acid (mM) Rate of formation of PGG2 (mM/min) 0.190 12.3 0.228 13.9 0.342 17.5 0.570 1.33 22.2 28.8 7.71 8.88 11.9 16.3 24.0 The kinetic data given in the table are for the reaction catalyzed by a mutant of prostaglandin endoperoxide synthase. Focusing here on the first two columns, determine the Vmax and Km of the enzyme. Vmax Km = mM/min mMarrow_forward
- NAC↔X™ Ph Ph OH Acid chlorides react with Grignard reagents to yield tertiary alcohols, two equivalents of Grignard reagent are required. The first equivalent reacts in a typical nucleophilic acyl substitution reaction to give a ketone. This ketone, however, is itself reactive in the Grignard reaction. Thus, the second equivalent adds to the ketone carbonyl carbon. Subsequent protonation yields the tertiary alcohol. Draw curved arrows to show the movement of electrons in this step of the mechanism. Arrow-pushing Instructions Ph :0: 1. 2 eq. CH3MgBr 2. H3O+ CH3 H3C CH3 H3C-MgBr Ph O: MgBr -CH3 CH3arrow_forwardDraw and name the major organic product for the reaction.arrow_forwardFill in the boxes with the appropriate reagents:arrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning