The halide shown is heated with sodium ethoxide in ethanol. Which structure is the major product?

AStructure A
BStructure B
CStructure C
DStructure D

Answer: D

The compound is 3-bromo-2-methylpentane. Ethoxide removes the tertiary beta-hydrogen on C-2 to give the trisubstituted 2-methylpent-2-ene (Saytzeff). The disubstituted 4-methylpent-2-enes are minor and the ether comes from SN2.

Practice Organic Reaction Mechanisms IV: Elimination More on Saytzeff vs Hofmann product from drawn halides

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