What dienes and dienophiles would react to give the following Diels-Alder products?

a)

b)

c)

d)

e)

f)

Short Answer

Expert verified

a)

b)

c)

d)

e)

f)

Step by step solution

01

Dienes and Dienophiles

Dienes are compounds that contain two C=C bonds, and dienophiles are those that contain one C=C bond.In the Diels-Alder reaction, these compounds joined together, forming a Diels-alder product.

02

Diene and Dienophile in (a)

In this compound, the diene contains two double bonds, and the dienophile has one functional group COCH3; when these are joined together, it results in the formation of the desired product.

Diene and Dienophile

03

Diene and Dienophile in (b)

In this compound, the diene contains two methoxy (-OCH3) groups, and the dienophile has one functional group COOCH2CH3; when these are joined together results in the formation of the desired product.

Diene and Dienophile

04

Diene and Dienophile in (c)

In this compound, the diene will be the furan ring, and the dienophile has one functional group CN; joining together results in the formation of the desired product.

Diene and Dienophile

05

Diene and Dienophile in (d)

In this compound, the diene will be the cyclohexene ring containing two double bonds, and the dienophile has two COOCH3 groups; when these are joined together results in the formation of the desired product.

Diene and Dienophile

06

Diene and Dienophile in (e)

In this compound, the diene contains one methoxy (-CH3) group, and the dienophile has four CN groups; when these are joined together, it forms the desired product.

Diene and Dienophile

07

Diene and Dienophile in (f)

In this compound, the diene will be a cyclopentadiene ring, and the dienophile has two ketone groups in the furan ring; when these are joined together results in the formation of the desired product.

Diene and Dienophile

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Most popular questions from this chapter

Question: When Br2 is added to buta-1,3- diene at -150C , the product mixture contains 60% of product A and 40% of product B. When the same reaction takes place at 600C , the product ratio is 10% A and 90% B.

a. Propose structures for products A and B (Hint: In many case, an allylic carbocation is more stable than a bromonium ion.)

b. Propose a mechanism to account for formation of both A and B.

c. Show why A predominates at -150C and B predominates at 600C .

d. If you had a solution of pure A, and its temperature were raised to600C , what would you expect to happen ? Propose a mechanism to support your prediction.

Show that the [4+2] Diels-Alder reaction is photochemically forbidden.

Question: When is added to buta-1,3- diene at -150C, the product mixture contains 60% of product A and 40% of product B. When the same reaction takes place at 600C, the product ratio is 10% A and 90% B.

a. Propose structures for products A and B (Hint: In many case, an allylic carbocation is more stable than a bromonium ion.)

b. Propose a mechanism to account for formation of both A and B.

c. Show why A predominates at -150C and B predominates at 600C .

d. If you had a solution of pure A, and its temperature were raised to 600C , what would you expect to happen ? Propose a mechanism to support your prediction.

Question: The central carbon atom of an allene is a member of two double bonds, and it has an interesting orbital arrangement that holds the two ends of the molecule at right angles to each other.

  1. Draw an orbital diagram of allene, showing why the two ends are perpendicular.
  2. Draw the two enantiomers of penta-2,3-diene. A model may be helpful.

In a strongly acidic solution, cyclohexa-1, 4-diene tautomerizes to cyclohexa-1, 3-diene. Propose a mechanism for this rearrangement, and explain why it is energetically favorable.

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