Question

Which of the following type of protons are chemically equivalent? A) homotopic B) enantiotopic C) diastereotopic A & B B & C

Answer 1

Answer:

A) homotopic and B) enantiotopic

Explanation:

Protons chemically equivalent are those that have the same chemical shift, also if they are interchangeable by some symmetry operation or by a rapid chemical process.

The existence of symmetry axes, Cn, that relate to the protons results in the protons being homotopic, that is chemically equivalent in both chiral and aquiral environments.

The existence of a plane of symmetry, σ, makes the protons related by it, are enantiotopic and these protons will only be equivalent in an aquiral medium; if the medium is chiral both protons will be chemically NOT equivalent. The existence of a center of symmetry, i, in the molecule makes the related protons through it enantiotopic and therefore chemically only in the aquiral medium.

Diastereotopic protons cannot be interconverted by any symmetry operation and they are different, with different chemical displacement.