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Magazine Chapter 7: Q51 (page 218)
Q 51 Normally, a trans alkene is more stable than its cis isomer trans-Cyclooctene, however, is less stable than cis-cyclooctene by 38.5 kJ/mol. Explain.
Short Answer
Answer
Trans alkene is more stable than cis alkene due to the less steric strain present in the trans-isomers.
Step by step solution
Stability of alkene
Trans alkene is more stable than cis alkene due to the less steric strain present in the trans-isomers. But this concept is not valid only above eight-membered ring systems. Above an eight-membered ring, cis form is more stable than trans-form due to more flexibility in the ring.
Explanation for trans-cyclooctene is less stable than cis-cyclooctene
After the eight-membered ring, the flexibility of the ring increases, so both the isomers of cyclooctene exist. But trans cyclooctene is less stable due to a large amount of strain when the present in the trans-form as compared to cis form
Isomers of cyclooctene have large energy differences due to a large amount of steric strain present in the isomers
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