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Chapter 8: Q47P (page 362)

What diene and what dienophile should be used to synthesize the following?

Short Answer

Expert verified

The diene and dienophile for all of the reactions are,

Step by step solution

01

Definition of Diels-Alder reaction

Diels Alder reaction is a pericyclic reaction where a diene and dienophile reacts to form a cyclic entity. This reaction is a reversible reaction. At high temperature, the cyclic compound breaks to get back the reactants,

02

Retro synthetic approach to Diels-Alder reaction

1. The double bond should be located in the product. The diene that was used to form the cyclic product had double bonds on either side of the existing double bond, so, that double bonds should be drawn removing the original double bond.

2. The new σ bonds are now on the other side of these double bonds. Deleting these σ bonds and putting a π bond between the two carbons whose σ bonds were deleted gives the needed reactants—that is, the diene and the dienophile.

03

Reaction mechanism of the given products

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Most popular questions from this chapter

What are the products of the following reactions?

The experiment shown next and discussed in Section 8.13 shows that the proximity of the chloride ion to C−2 in the transition state causes the 1,2−addition product to be formed faster than the 1,4−addition product.

a. Why was it important for the investigators to know that the preceding reaction was being carried out under kinetic control?

b. How could the investigators know that the reaction was being carried out under kinetic control?

Rank the indicated hydrogen in the following compounds from most acidic to least acidic:

What are the major 1,2- and 1,4-addition products of the following reactions? For each reaction, indicate the kinetic and the thermodynamic product.

Identify the product of the following reaction. (Hint:It has a fused bicyclic ring.)
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