Concept:Wurtz reaction couples alkyl halides using sodium metal in dry ether, but tertiary alkyl halides fail due to steric hindrance and elimination.
Explanation:In Wurtz reaction, two alkyl halide molecules react with sodium to form a higher alkane:
2R−X+2Na→R−R+2NaXThis reaction works best with primary alkyl halides.
For example:
2CH3Br+2Na→CH3−CH3+2NaBr2C2H5Cl+2Na→C2H5−C2H5+2NaClOption A,
(CH3)3CCl is tert-butyl chloride, a tertiary alkyl halide.
Due to high steric crowding, tertiary halides preferentially undergo elimination with sodium, giving an alkene instead of the coupled product.
Therefore, Wurtz reaction is not possible with
(CH3)3CCl.
Answer:Option A:
(CH3)3CCl