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Logic Puzzle #20: Which CH2 will split?

September 2, 2011

Diastereotopic protons that are also anisochronous exhibit different chemical shifts. The purpose of this puzzle is to understand a general trend for CH2 groups.

If the following structure, shown below, were dissolved in CDCl3 and a 1H NMR spectrum were acquired on a 500 MHz instrument, which of the following three CH2’s would most likely be anisochronous?

IUPAC: methyl 7-hydroxy-3,5-dioxo-7-phenylheptanoate


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