Shifts and Signals

Chemistry Level pending

An extension to Teleanu Florin's problem (for context you might want to go through his problem)

This is the compound that was investigated in the problem, we call it compound X:

Let all the hydrogen atoms bonded to the carbon atoms in the cyclopentane ring be denoted as Ring Hydrogens or \(H_{r}\) and the remaining hydrogen on the top of the cyclopropane ring be called the Axial Hydrogen or \(H_{a}\). The hydrogen atoms present in the axial methyl group are denoted as \(H_{m}\).

Let's say we have some kind of reaction that allows us to remove a \(H_{r}\) atom and replace it with a deuterium (\(D_{r}\)) without changing the rest of the molecule.

We now turn to H-NMR spectra of 3 compounds:

  • Compound X
  • Compound Y (one \(H_{r}\) is replaced)
  • Compound Z (two \(H_{r}\) are replaced)

(All compounds are placed in solutions that are above 390K)

We now define 2 quantities \(\alpha\) and \(\beta\). \(\alpha\) is the number of H-NMR signals obtained from compound Y and \(\beta\) is the number of H-NMR signals obtained from compound Z

What is the value \(\alpha\) - \(\beta\) ?

Bonus:

Devise a reaction that can replace \(H_{r}\) with \(D_{r}\)

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