The process of dehalogenation involves the removal of halogen atoms from an organic compound. When this process occurs in a vicinal dihalo alkane (a compound in which two halogen atoms are attached to adjacent carbon atoms), the product formed is... Read More
The process of dehalogenation involves the removal of halogen atoms from an organic compound. When this process occurs in a vicinal dihalo alkane (a compound in which two halogen atoms are attached to adjacent carbon atoms), the product formed is an alkene.
Reaction Example:
CH₂Br–CH₂Br → CH₂=CH₂ + 2HBr
This transformation takes place under the influence of a reducing agent such as zinc dust in the presence of alcohol (Zn/EtOH). The zinc reacts with halogen atoms to remove them from the molecule, leading to the formation of a carbon–carbon double bond.
Mechanism:
Zinc donates electrons to halogen atoms, forming ZnX₂ (where X is the halogen).
Both halogen atoms are removed from adjacent carbon atoms.
The carbon atoms, now electron-deficient, form a π-bond, resulting in an alkene.
Vicinal dihalo alkanes vs. Geminal dihalo alkanes:
Vicinal dihalo alkane: Halogen atoms on adjacent carbon atoms → form alkene after dehalogenation.
Geminal dihalo alkane: Both halogens on same carbon atom → may form carbene or other products, not a simple alkene.
Example Reaction:
1,2-Dibromoethane → Ethene + 2HBr
(CH₂Br–CH₂Br → CH₂=CH₂ + 2HBr)
Key Points:
Type of reaction: Dehalogenation (removal of halogens).
Reagent used: Zinc in alcohol.
Product formed: Alkene (due to formation of C=C bond).
Important condition: Halogens must be on adjacent carbons (vicinal).
Thus, alkenes are specifically produced from the dehalogenation of vicinal dihalo alkanes.
✅ Correct Option: C) Vicinal dihalo alkane
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