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- The 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 20.34.9. Determine the product of the following Diels-Alder reaction. CO₂Et 206°CMechanism 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.
- Which combination of reactants would undergo a Diels-Alder reaction the most quickly?5. The Diels-Alder reaction can also occur in an intramolecular fashion. Draw the two transition states leading to products in the following reaction: COOCH3 ÇOOCH3 COOCH3 H 180°C, 5h 75% H 65% 35%Draw the structure of the product of the Diels-Alder reaction below. H3C CH3 O || O || + CH3OC-CEC-COCH3
- Is the following true or false? To catalyse a Diels-Alder reaction a common approach involves the use of a Lewis acid capable of lowering the LUMO of the dienophile.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.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.
- Which of the following Diels-Alder reactions would be fastest? Diels-Alder CH=O OCH3 Diels-Alder Diels-Alder + || OCH3 CH=O + Diels-Alder70 ins210 V16225050 panx qalborgo 3) In a recently-published synthesis of yohimbine (used in folk medicine as an aphrodisiac), the Diels-Alder reaction was used to form a new ring during a key step. R OtBu Diels-Alder a. Draw a circle around the four atoms of the diene group in this molecule. b. Draw a square around the two atoms of the best dienophile group in this molecule. c. Draw the product of this reaction, ignoring stereochemistry.Which of the following is the most reactive diene in a Diels-Alder reaction? A) I B) II CI D) IV IV