Q 11-11-42 E-a - Organic Chemistry (Mcmurry)

Question

Which reactant in each of the following pairs is more nucleophilic? Explain.  

a) NH₂^- or NH₃

Step-by-Step Solution

Answer

NH₂^- 

Nucleophile

In chemistry, nucleophiles are negatively charged ions or neutral species with only one electron available for bonding.

Rules to identify more nucleophilic species

1. Nucleophile attacking the same atom then nucleophilicity is same as basicity that more basic species is more nucleophilic in nature.
2. Nucleophilicity increases in going down in a group of the periodic table.
3. A negatively charged nucleophile is more nucleophilic than a neutral nucleophile due to a negative charge.

More nucleophiles among NH 2 - or NH 3

On the basis of:

Rule 1: Nucleophile attacking the same atom then nucleophilicity is same as basicity that more basic species is more nucleophilic in nature.

Rule3: A negatively charged nucleophile is more nucleophilic than a neutral nucleophile due to a negative charge.

NH₂^- is more nucleophilic than NH₃