When can the molecule 2-butene, #C_4H_8#, undergo a geometric change called cis-trans isomerization?
1 Answer
But-2-ene can undergo cis-trans isomerization
- Thermally
- Photochemically
- By acid catalysis
- By free radical catalysis
Explanation:
The cis-trans isomerization of but-2-ene requires breaking of the π bond.
The minimum energy required for isomerization is 267 kJ/mol.
Thermal Isomerization
At temperatures of about 500 °C the molecules have enough kinetic, vibrational, and rotational energy that the π bond breaks and isomerization can take place.
Photochemical Isomerization
A quantum of light can excite a π electron to a π* orbital and allow free rotation about the central C-C bond.
(from www.tutorvista.com)
In the excited π* state, the double bond is effectively reduced to a single bond, and one methyl group can rotate relative to the other.
The isomerization can be accomplished by providing another pathway with a lower activation energy (catalysis).
Acid-Catalyzed Isomerization
In the presence of strong acids, which act as catalysts, the isomerization can take place at room temperature.
The proton adds reversibly to the π bond forming a singly-bonded carbocation.
There is a temporary free rotation about the single bond before the proton leaves to regenerate the π bond.
Free-Radical Catalyzed Isomerization
If we add iodine, the temperature required for the isomerization drops drastically.
Iodine sets up an equilibrium with iodine atoms.
Then the mechanism proceeds as below.
(from faculty.chem.queensu.ca)