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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
Retro Diels-Alder: show a combination of diene and dienophile that would result in each Diels-Alder adduct.
Since chair forms can be cumbersome to deal with, always convert them to plain "overhead view" structures before doing the problem.
When in doubt, use numbering.
Predict the product for each Diels-Alder reaction. Indicate stereochemistry where appropriate.
Chair forms can be difficult to draw, so it's a good diea to draw the "overhead view" first.
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.
Rank the following dienes in order of decreasing reactivity with a dienophile in a Diels-Alder reaction. (1 = most reactive).
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.
