When 3-iodo-3-ethylpentane is treated with sodium methoxide in methanol, the major organic product is an ______ that is generated through an ______ mechanism.
A) ether, SN1
B) ether, SN2
C) ether, E1
D) alkene, E2
E) alkene, E1
The alkyl halide is a tertiary alkyl halide and the methoxide base is a strong base. Owing to steric effects, tertiary alkyl halides often undergo elimination instead of substitution reaction with strong bases. The elimination occurs via an E1 mechanism because the tertiary carbocation formed is stable.
