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For the study of reaction mechanism in organic chemistry isotopic labeling, e. g. with 2 H or 17 O cOrganic Chemistry Chemistry Question

Atom Mobility (Dynamics ) in Organic Compounds

For the study of reaction mechanism in organic chemistry isotopic labeling, e. g. with 2 H or 17 O can give valuable information. Modern NMR techniques are able to “see“ deuterium 2 H and the oxygen isotope 17 O. As an example, the introduction of isotopic labels in 4-hydroxybutan-2-one is considered.

a, b, c, d are hydrogen atoms, x, y are oxygen atoms and m is a carbon atom.

4.1.

The substrate is treated with 2 H2O at pH = 10. Rank the order the exchange (introduction) of deuterium atoms ( 2 H) from first to last.
First     last.

Model Answer

a >> c, d > b

4.2.

Similarly the substrate is treated with H2 17 O at pH = 10. Rank the order of introduction of 17 O from the first to the last.
First   last.

Model Answer

y > x

4.3.

Do you consider the exchange method appropriate for the introduction of a 13 C at position m. Yes or No?

Model Answer

No

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