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

Question

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

b) H₂O or CH₃CO₂^-

Step-by-Step Solution

Answer

CH₃CO₂^- 

Nucleophile

The nucleophiles are the negatively charged ions or the neutral species with the lone pair of electrons ready to bond.

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.
2. Nucleophilicity increases in going down in a periodic table group.
3. A negatively charged nucleophile is more nucleophilic than a neutral nucleophile due to a negative charge.

More nucleophiles among H 2 O or CH 3 CO 2 -

Based on:

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

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

CH₃CO₂^- is more nucleophilic than H₂O.