4) Consider the following reactions that are either Diels-Alder or rely on a Diels-Alder step: a) Cyclopentadienone is a relatively unstable molecule that dimerizes rapidly at room temperature to give a molecule with the molecular formula of C10H8O2. Draw this molecule. b) Propose a synthesis of the following molecule starting with cyclopentadiene and any other necessary reagents CHO OHC CO₂Et
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- Compounds P and Q can undergo a Diels-Alder reaction to form two regioisomeric products R and S as shown in Figure 5. OMe O C8H12O2 R C8H12O2 S Figure 5 Draw the chemical structures of regioisomeric compounds R and S. Using possible resonance contributors of P and Q predict which of the two regioisomers will be favoured in the reaction. Using curly arrows, draw the mechanism for the reaction of P and Q to form the dominant regioisomer you have predicted in your answer to part (ii) above.8) Predict the two products that form in following Diels-Alder reaction Circle the major product. CH₂O CH₂OCH, H O₂N6) The Diels-Alder reaction of anthracene (which is achiral) and maleic anhydride (also achiral) results in the formation of an achiral product. This is not always the case (where two achiral reactants form an achiral product). a) Propose a Diels-Alder reaction where two achiral starting materials result in the formation of a chiral product. b) Would this chiral product be a single enantiomer or a racemic mixture?
- 10. The following compound was produced in a Diels-Alder reaction. COOH a) How many sp³ hybridized carbons are in this molecule? b) Is this molecule chiral? c) Are the carboxylic acid substituents electron donating group or electron withdrawing group? d) Draw the diene and dienophile which would react together to give this product.Mechanism The Diels-Alder reaction is part of a class of reactions known as a cycloaddition reaction. This reaction is specifically a [4+2] cycloaddition which is a concerted (one-step) process in which two new carbon - carbon sigma bonds are formed from two pi bonds. For the first Diels - Alder step of the mechanism fill in the arrows needed for the transformation. The rest of the mechanism is drawn for you. OH Show mechanism arrows for this step! 4 + 2 cycloaddition OH H D- & H+ transfer OH Nuc acyl substitution H L.G.7. At room temperature cyclopentadiene reacts with itself to form dicyclopentadiene in a Diels-Alder reaction. a) draw the self reaction of cyclopentadiene 20°C. b) When dicyclopentadiene is heated to boiling (170°C), the retor-Diels-Alder reaction occurs producing 2 moles of cyclopentadiene. Explain this observation in terms of free energy, enthalpy and entropy. c) If the AHxn = -75 kJ/mol and the ASpxn = -226 J/mol K, What temperature would be required for the reaction to be at equilibrium (Keq = 1).
- A) Write the mechanism and predict the products for the following reaction. Label each product as the thermodynamic product or the kinetic product. Write a few sentences explaining which product would predominate at low temperature and which would predominate at high temperature and explain the reason for this result. HBr ABd B) Choose reagents that would give the following product in a Diels-Alder reaction: C) Predict the major and minor product for the following Diels-Alder reaction:True or False: Acetylene is a naturally occurring conjugated diene True or False: The Diels-Alder reaction has the stereochemistry of the dienophile is retained in the product. True or False: When looking at kinetic vs. thermodynamic products the kinetic product predominates at low temperature. True or False: the mechanism of the Diels-Alder reaction is three π bonds break; one σ bond and two π bonds form.The following are several isomers of C10H14 with two fused six-membered rings. A B D E G H (a) Identify which will react with ethene in a Diels-Alder reaction and which will not. (b) Draw one more isomer with two fused six-membered rings that will react with ethene in a Diels-Alder reaction.
- Furan and maleimide undergo a Diels–Alder reaction at 25 °C to give the endo isomer of the product. When the reactiontakes place at 90 °C, however, the major product is the exo isomer. Further study shows that the endo isomer of theproduct isomerizes to the exo isomer at 90 °C.furan: O maleimide:OON H(a) Draw and label the endo and exo isomers of the Diels–Alder adduct of furan and maleimide.(b) Which isomer of the product would you usually expect from this reaction? Explain why this isomer is usually favored.(c) Examine your answer to (b) and determine whether this answer applies to a reaction that is kinetically controlled orone that is thermodynamically controlled, or both.(d) Explain why the endo isomer predominates when the reaction takes place at 25 °C and why the exo isomer predominates at 90 °CCyclopentadiene is unusually acidic for a hydrocarbon. Which of the following explains why that is? The carbon atoms of cyclopentadiene are all sp hybridized. A В Cyclopentadiene is aromatic. Removal of a proton from cyclopentadiene yields an C aromatic anion. Removal of a hydrogen atom from cyclopentadiene yields a highly stable free radical. D Removal of a hydride ion from cyclopentadiene produces an E aromatic cation. H H. cyclopentadieneThe following triene undergoes an intramolecular Diels-Alder reaction to give a bicyclic product. Propose a structural formula for the product. Account for the observation that the Diels-Alder reaction given in this problem takes place under milder conditions (at lower temperature) than the analogous Diels-Alder reaction shown in Problem 20.34.