When 3-bromo-3-methylpentane is heated with sodium methoxide in methanol, an elimination reaction occurs. What is the IUPAC name of the major organic product formed?

Step-by-step solution

The reaction of a tertiary alkyl halide (3-bromo-3-methylpentane) with a strong, unhindered base (sodium methoxide) under heating conditions proceeds via an E2 elimination mechanism. According to Saytzeff's rule, the major product is the more highly substituted alkene. The substrate has two types of -hydrogens: those on the adjacent methylene carbons (C2 and C4) and those on the methyl group attached to C3. Elimination of a hydrogen from the methylene group yields 3-methylpent-2-ene, which is a trisubstituted alken