Which diene does NOT undergo the Diels-Alder reaction readily?

Acyclopenta-1,3-diene
B(2E,4E)-hexa-2,4-diene
C2,3-dimethylbuta-1,3-diene
D(2Z,4Z)-hexa-2,4-diene

Answer: D

The diene must be able to adopt the s-cis conformation. In (2Z,4Z)-hexa-2,4-diene the two inward-pointing methyl groups clash strongly in the s-cis form, so it hardly reacts. Cyclopentadiene is locked s-cis, and the E,E-diene and 2,3-dimethylbutadiene can reach it easily.

Practice Hydrocarbons More on Conjugated dienes and Diels-Alder reaction

Previous questionNext question

More questions on Conjugated dienes and Diels-Alder reaction

Penta-1,3-diene is more stable than penta-1,4-diene mainly because of NEET level
Buta-1,3-diene reacts with dimethyl fumarate (dimethyl (E)-but-2-enedioate). The Diels-Alder adduct is JEE Main level
Buta-1,3-diene reacts with 1 mol of HBr at 40 degC under thermodynamic control. The major product is JEE Main level
Cyclohexa-1,3-diene is treated with O3 followed by Zn/H2O. The organic products are JEE Main level
Which of the following dienophiles reacts fastest with buta-1,3-diene in a normal-electron-demand Diels-Alder reaction? JEE Main level
2,3-Dimethylbuta-1,3-diene reacts with propenal (CH2=CH-CHO) in a Diels-Alder reaction. The product is JEE Advanced level