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

Question

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

d) (CH₃)₃P or (CH₃)₃N

Step-by-Step Solution

Answer

(CH₃)₃P 

Nucleophile

It is the negatively charged ions or neutral species that possess a single electron that is nucleophiles.

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 (CH 3 ) 3 P or (CH 3 ) 3 N

On the basis of:

1. Rule2: Nucleophilicity increases in going down in a group of the periodic table.

P and N belong to group 15 of the periodic table and P is shown above N in the group.

 

(CH₃)₃P is more nucleophilic than (CH₃)₃N