Draw the reactants that would be used to form this cyclohexene derivative in a Diels-Alder reaction. Include any relevant stereochemical configurations. Draw Diene + Draw Dienophile Q I I I I

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A2 What is the inverse electron demand Diels–Alder reaction? Please pick a pair of a diene and a dienophile from the following dienes and dienophile that will undergo this type of reaction. Please show how this reaction works using Frontier Molecular Orbitals. What is the reaction product?

Of the three 1,4-diphenyl-1,3-butadiene isomers (E,E or E,Z or Z,Z) indicate the most suitable diene that can be used as a reactant in a Diels-Alder reaction. Explain your choice.

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This is a Diels-Alder reaction between furan + maleic anhydride (endo and exo products). For each cycloaddition product, draw in all hydrogen atoms, and write the molecular formula below.

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.

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).

Draw the starting diene and dieneophile

6. Predict the major product for the following Diels-Alder reaction. 7. Which diene and dienophile would react to give the following Diels-Alder product? Сон 8. Which diene and dienophile would react to give the following Diels-Alder product? Ill