The symmetrical diol shown is treated with dilute H2SO4 and warmed. Which structure is the pinacol rearrangement product?

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The symmetrical diol shown is treated with dilute $H X_{2} SO X_{4}$ and warmed. Which structure is the pinacol rearrangement product?

AStructure A
BStructure B
CStructure C
DStructure D

Answer: D

The diol is 3,4-diethylhexane-3,4-diol. Loss of water gives a tertiary cation, an ethyl group migrates from the other carbinol carbon, and the oxygen becomes a ketone. The product is 4,4-diethylhexan-3-one; the epoxide and the alkene are not rearrangement products.

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Answer: D

More questions on Pinacol rearrangement products of drawn diols

The symmetrical diol shown is treated with dilute $H X_{2} SO X_{4}$ and warmed. Which structure is the pinacol rearrangement product?