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EEJ MAIN Chemistry QUESTION #7124
Question 1
The reaction of $2$-chloro-$2$-methylpentane with sodium methoxide ($NaOCH_3$) in a methanol solvent results in the formation of:
  • Only substitution products
  • Only elimination products
  • A mixture of substitution and elimination products✔️
  • No reaction occurs
Correct Answer Explanation
The substrate is a 3° (tertiary) alkyl halide. When treated with a strong base/nucleophile like $CH_3O^-$, it undergoes both $S_N1$ (substitution) to form an ether and $E2$ (elimination) to form alkenes. Therefore, the result is a mixture of products like $2$-methoxy-$2$-methylpentane and $2$-methylpent-$2$-ene.