Q13-40E - Organic Chemistry (Mcmurry)

Question

Identify the indicated sets of protons as unrelated, homotopic, enantiotopic, or diastereotopic:

a. 

b.

c. 

Step-by-Step Solution

Answer

1. Enantiotopic

2. Diastereotopic

3. Diastereotopic

Step-by-Step Solution Step 1 : Topicity

It is defined as the relation between the substituent and the structure with which they are stereochemically attached like homotopic, enantiotopic, and diastereotopic.

Step 2: Homotopic

It is defined as the group in which 1 atom like hydrogen is replaced by the other atom when the rest are fixed and the molecule remains the same stereochemically and produces the same chemical shift.

Step 3: Enantiotopic

It is defined as the group in which 1 atom like hydrogen is replaced by another  atom when the rest are fixed and the molecule changes its stereo and from mirror images and produces the same  chemical shift majority by if have chiral carbon produce different chemical shift like compound an as shown:

Compound a

Step 4: Diastereotopic

It is defined as the group in which 1 atom like hydrogen is replaced by another atom when the rest are fixed and the molecule changes its stereo but is not a mirror image and produces the different chemical shift for every atom-like compound b and c as shown:

                                             Compound b    

    

                                                

Compound c