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Chapter 16: PROBLEM 16.49 (page 636)

Question: Draw the products of the following Diels鈥揂lder reactions. Indicate stereochemistry where appropriate.

a.

b.

c.

d.

Short Answer

Expert verified

a.

Products of a.

b.

Products of b.

c.

Product of c.

d.

Product of d.

Step by step solution

01

Detect the diene and dienophile

Find the 1,3-diene and the dienophile in the given reactions. Place the diene on the left and the dienophile on the right side.

02

Cleavage of bonds

The three double bonds of the 1,3-conjugated diene and the dienophile cleave to form new bonds such that a ring is formed.

03

Products of the given reactions

a. The dienophile is re-drawn such that the double bond is right in front of the conjugated diene. The double bonds are broken to form a ring.


Products of a

b. The structures are re-drawn, and the bonds are cleaved to form a ring.

Products of b

c. The structures are re-drawn, and the bonds are cleaved to form a ring.

Product of c

d. The structures are re-drawn, and the bonds are cleaved to form a ring.

Product of d

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Most popular questions from this chapter

Question: Which of the following systems are conjugated?

a.

b.

c.

d.

e.

f.

Question: Classify each diene as isolated or conjugated.

a.

b.

c.

d.

Question: What diene and dienophile are needed to prepare each Diels鈥揂lder product?

a.

b.

c.

d.

Question: Explain why the cyclopentadienide anion A gives only one signal in its 13C NMR spectrum.

Question: Explain, with reference to the mechanism, why addition of one equivalent of HCl to diene A forms only two products of electrophilic addition, even though four constitutional isomers are possible.
See all solutions

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