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 # 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 # 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.