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Diels-Alder Post-lab questions F17. 1) Why do the methylene protons (Ha & Hb) exhibit
different chemical shifts? Hb Ha Hd 2) Why do Diels-Alder reactinns hninoll
Solution
Methylene protons adjacent to a chiral center will be non equivalent, despite the fact that there is
free rotation about the cabon-carbon bond. Such protons are described as diastereotopic, since
replacement of either of the two hydrogen in turn by a group X produces a pair of diastereomers.

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