MS 911 - Diels-Alder Practice

Submitted by Matt on August 6, 2011.

Textbook and Chapter: Carey and Giuliano 8th Ed. (2010), Chapter 10

Keyword: Diels-Alder

Description: Diels Alder stuff- predict the products, retrosynthesis, and dienophile reactivity.

Total Problems: 5

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Problem # 570

Rank the following dienes in order of decreasing reactivity with a dienophile in a Diels-Alder reaction. (1 = most reactive).
Solution
To undergo a Diels-Alder reaction, a dienophile must be in s-cis conformation.

The bicylic compound below is locked into s-trans conformation; it can never rotate into s-cis conformation and so can't undergo a Diels-Alder reaction.

Of the other two compounds, the middle compound most easily rotates into s-cis conformation, and so will undergo a Diels-Alder reaction the fastest. The compound on the right has steric strain when in s-cis conformation, and so won't do Diels-Alder as easily.

Problem Details
MendelSet practice problem # 570 submitted by Matt on July 8, 2011.
Subject: Organic Chemistry
Subject Topic(s): Diels-Alder
Question Type: Concept (explain why this is so..)
Keyword(s): Diels-Alder
Problem # 574

Predict the product for each Diels-Alder reaction. Indicate stereochemistry where appropriate.
Solution
When approaching Diels-Alder problems, it's always good to user numbering: the product is always a cyclohexene compound.

In b), the trans dienophile leads to a trans product.

In c), the dienophile is an alkyne, and so becomes an alkene in the product.

Problem Details
MendelSet practice problem # 574 submitted by Matt on July 8, 2011.
Subject: Organic Chemistry
Subject Topic(s): Diels-Alder
Question Type: Reactions (predict the product, show the starting material..)
Keyword(s): Diels-Alder
Problem # 575

Predict the product for each Diels-Alder reaction. Indicate stereochemistry where appropriate.
Solution
Chair forms can be difficult to draw, so it's a good diea to draw the "overhead view" first.

Problem Details
MendelSet practice problem # 575 submitted by Matt on July 8, 2011.
Subject: Organic Chemistry
Subject Topic(s): Diels-Alder
Question Type: Reactions (predict the product, show the starting material..)
Keyword(s): Diels-Alder
Problem # 576

Retro Diels-Alder: show a combination of diene and dienophile that would result in each Diels-Alder adduct.
Solution
When in doubt, use numbering.

Problem Details
MendelSet practice problem # 576 submitted by Matt on July 8, 2011.
Subject: Organic Chemistry
Subject Topic(s): Diels-Alder
Question Type: Reactions (predict the product, show the starting material..)
Keyword(s): Diels-Alder
Problem # 577

Retro Diels-Alder: show a combination of diene and dienophile that would result in each Diels-Alder adduct.
Solution
Since chair forms can be cumbersome to deal with, always convert them to plain "overhead view" structures before doing the problem.

Problem Details
MendelSet practice problem # 577 submitted by Matt on July 8, 2011.
Subject: Organic Chemistry
Subject Topic(s): Diels-Alder
Question Type: Reactions (predict the product, show the starting material..)
Keyword(s): Diels-Alder

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MS 911 - Diels-Alder Practice

MS 911 - Diels-Alder Practice

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