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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 蟽 bonds are now on the other side of these double bonds. Deleting these 蟽 bonds and putting a 蟺 bond between the two carbons whose 蟽 bonds were deleted gives the needed reactants鈥攖hat is, the diene and the dienophile.

03

Reaction mechanism of the given products

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Most popular questions from this chapter

a. Why does deuterium add to C-1 rather than to C-4 in the preceding reaction?

b. Why was DCl rather than HCl used in the reaction?

a. How many linear dienes have molecular formula C6H10? (Disregard cis-trans isomers.)

b.How many of the linear dienes in part a are conjugated dienes?

c.How many are isolated dienes?

d. How many are cumulated dienes?

Refer to the electrostatic potential maps on p. 368 to answer the following questions:

a. Why is the bottom part of the electrostatic potential map of pyrrole blue?

b. Why is the bottom part of the electrostatic potential map of pyridine red?

c. Why is the center of the electrostatic potential map of benzene more red than the center of the electrostatic

potential map of pyridine?

Protonated cyclohexylamine has aKa=1脳10鈭�11. Using the same sequence of steps as in Problem 94 , determine which is a stronger base, cyclohexylamine or aniline.

Draw the resonance contributors for the following carbocation
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