Question
Identify the product obtained when 2- Chloro - 2 - methylbutane is reacted with sodium metal in presence of dry ether?
Identify the product obtained when 2- Chloro - 2 - methylbutane is reacted with sodium metal in presence of dry ether?
D. 3, 3, 4, 4 - tetramethylhexane
The given reactant is 2-chloro-2-methylbutane, which has the structure CH_3-C(Cl)(CH_3)-CH_2-CH_3. When reacted with sodium metal in the presence of dry ether, it undergoes the Wurtz reaction. The reaction proceeds via the formation of an alkyl free radical. The cleavage of the C-Cl bond yields the radical CH_3-C^ (CH_3)-CH_2-CH_3. Two such radicals dimerize to form the final alkane product: 2 CH_3-C(Cl)(CH_3)-CH_2-CH_3 + 2 Na CH_3-CH_2-C(CH_3)_2-C(CH_3)_2-CH_2-CH_3 + 2 NaCl The longest continuous carbon chain in the product contains 6 carbon atoms, making the parent chain a hexane. Numbering the chain from either end gives substituents at the 3rd and 4th positions. There are four methyl groups attached to the main chain, two at C-3 and two at C-4. Thus, the IUPAC name of the product is 3,3,4,4-tetramethylhexane.
Related: Chemistry — Haloalkanes and Haloarenes · All PYQ Banks