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Chapter 16: PROBLEM 16.19 (page 623)

Question: Draw the product formed when each diene and dienophile react in a Diels–Alder reaction.

a.

b.

c.

Short Answer

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Answer

a.

b.

c.

Step by step solution

01

Diels-Alder reaction

Diels-Alder reaction is an addition reaction where the participants are a 1,3-diene and a dienophile. A cyclic six-membered ring is formed as a product of this reaction.

The reaction occurs in the presence of heat.

The general reaction scheme is shown below.

Diels-Alder reaction

02

Determination of products

a. The diene and dienophile are redrawn and arranged, and the reaction is shown below.

Diels-Alder reaction a

b.The s-trans conformation of the diene is converted to s-cis, and both diene and dienophile are redrawn and arranged accordingly. The reaction is given below.

Diels-Alder reaction b

c. The diene is in s-trans conformation. It is rotated and brought into s-cis in order to perform the reaction, as shown below.

Diels-Alder reaction c

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Most popular questions from this chapter

Question: Treatment of alkenes A and B with HBr gives the same alkyl halide C. Draw a mechanism for each reaction, including all reasonable resonance structures for any intermediate.

Question: Explain why ferulic acid, a natural product found in rice, oats, and other plants, is both an antioxidant and a sunscreen.

Question: Explain why methyl vinyl ether CH2=CHOCH3 is not a reactive dienophile in the Diels-Alder reaction.

Question: Draw the products of each reaction. Indicate the stereochemistry of Diels–Alder products.

a.

b.

c.

d.

Question: Use resonance theory and the Hammond postulate to explain why 3-chloroprop-1-eneCH2=CHCH2Cl is more reactive than 1-chloropropaneCH3CH2CH2Cl in SN1 reactions.
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