Question

Identify the nucleophilicity order in the following $H{O^ - }C{H_3}CO{O^ - }$ in protic solvent:

Answer 1

Hint: Here in this question we will first define the term nucleophilic strength and also the protic solution. Then we will come to the comparison of these two given organic compounds. As we know, the order of nucleophiles in which the nucleophilic atoms are the same is the same as their basicity order. The addition of alkyl groups increases the basicity of the compound.

Complete answer:
Nucleophilicity- It is defined as the ability of a nucleophile to react with an electron deficient compound or electron deficient center.
Protic solvent- It is defined as a solvent which contains ${H^ + }$ ions; in a protic solvent the hydrogen atom is bound to the oxygen atom and a nitrogen atom. The compound in which hydrogen is found in the protic solvent is hydroxyl group, amine group and hydrogen fluoride. The nucleophilicity order of $C{H_3}O{O^ - }$ is more than the nucleophile $O{H^ - }$
The $O{H^ - }$ ion is surrounded by tight shell solvent molecules which hinder its ability to attack the substrate therefore its nucleophilicity decreases.

Note: A very electronegative atom is a poor nucleophile, as it is not willing to share its electrons. The charge density on each atom of the oxygen is decreased, therefore acetate ion is not a strong nucleophile. As we know the nucleophilicity and basicity are related but they are not measured in the same way. For example , $O{H^ - }$ is a strong base than $C{N^ - }$ but when we see their nucleophilicity $C{N^ - }$ is a strong nucleophile than $O{H^ - }$ . The order of nucleophilicity increases as we go down in the periodic table in case of polar protic solvents.